Gen Chemistry Bonds, Properties Verified Test Bank Chapter 1 - Organic Chemistry 4e | Test Bank by Klein by David R. Klein. DOCX document preview.

Gen Chemistry Bonds, Properties Verified Test Bank Chapter 1

Organic Chemistry, 4e (Klein)

Chapter 1 A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

1) Chemical reactions occur as a result of ________.

A) the attraction between opposite charges

B) the nucleus—nucleus interactions

C) the motion of electrons

D) like atoms interacting

E) combining two chemicals

Diff: 1

Learning Objective: 1.1 Compare and contrast organic and inorganic compounds

2) From the following, identify the item which does not contain organic compounds.

A) medicine

B) socks

C) a plant

D) a coin

E) a plastic cup

Diff: 1

Learning Objective: 1.1 Compare and contrast organic and inorganic compounds

3) What is the difference between inorganic and organic compounds?

A) organic compounds do not contain carbon

B) organic compounds contain carbon

C) organic compounds are without pesticides

D) inorganic compounds contain carbon

E) inorganic compounds are composed exclusively of transition metal elements

Diff: 1

Learning Objective: 1.1 Compare and contrast organic and inorganic compounds

4) Constitutional isomers do not differ in ________.

A) physical properties

B) atomic connectivity

C) molecular formula

D) name

E) constitution

Diff: 1

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

5) What is the relationship between the following compounds?

An illustration shows the structures of two compounds. The first compound has a five-carbon chain in which C 1 and C 3 are each bonded to two hydrogen atoms, C 1 is double bonded to C 2, C 2 is bonded to a hydrogen atom, C 4 is double bonded to an oxygen atom carrying two lone pairs of electrons, and C 5 is bonded to three hydrogen atoms. The second compound has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 is double bonded to an oxygen atom carrying two lone pairs of electrons, C 3 is bonded to a carbon atom which is further bonded to three hydrogen atoms, C 3 is double bonded to C 4, and C 4 is bonded to two hydrogen atoms.

A) isotopes

B) constitutional isomers

C) the same structure

D) composed of different elements

E) no relationship

Diff: 1

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

6) What is the relationship between the following compounds?

An illustration shows the structures of two compounds. The first compound has a four-carbon chain in which C 1 and C 4 are each bonded to three hydrogen atoms, C 2 is bonded to two hydrogen atoms, and C 3 is replaced by an oxygen atom carrying two lone pairs of electrons. The second compound has a three-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 are each bonded to two hydrogen atoms, C 3 is further bonded to an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom.

A) resonance isomers

B) constitutional isomers

C) empirical isomers

D) isotopes

E) There is no relationship

Diff: 1

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

7) Carbon is considered to be ________.

A) tetravalent

B) divalent

C) trivalent

D) monovalent

E) pentavalent

Diff: 1

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

8) Which of the following compounds are constitutional isomers of each other?

An illustration shows the structures of four compounds. The first compound labeled 1 has a benzene ring in which C 1 is bonded to a bromine atom. C 2 is bonded to a chlorine atom. C 3 and C 6 are each bonded to a carbon atom which is further bonded to three hydrogen atoms. C 4 and C 5 are each bonded to a hydrogen atom. The second compound labeled 2 has a benzene ring in which C 1, C 4, C 5, and C 6 are each bonded to a hydrogen atom. C 2 is bonded to a two-carbon chain in which C 1 is bonded to a bromine atom and a hydrogen atom and C 2 is bonded to three hydrogen atoms. C 3 is bonded to a chlorine atom. The third compound labeled 3 has a benzene ring in which C 1 is bonded to a bromine atom. C 2 and C 6 are each bonded to a carbon atom which is further bonded to three hydrogen atoms. C 3 and C 4 are each bonded to a hydrogen atom. C 5 is bonded to a chlorine atom. The compound labeled 4 has a benzene ring in which C 1 and C 4 are each bonded to a bromine atom. C 2 is bonded to a chlorine atom. C 3 and C 5 are each bonded to a carbon atom which is further bonded to three hydrogen atoms. C 6 is bonded to a hydrogen atom.

A) I and II

B) III and IV

C) I, II and IV

D) II, III and IV

E) I, II, and III

Diff: 2

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

9) Which of the following compounds are constitutional isomers of each other?

An illustration shows the structure of four compounds. The first compound labeled 1 has a two-carbon chain in which C 1 is bonded to two hydrogen atoms and a chlorine atom, and C 2 is bonded to two chlorine atoms and a hydrogen atom. The compound labeled 2 has a two-carbon chain in which C 1 and C 2 are each bonded to two chlorine atoms and a hydrogen atom, respectively. The compound labeled 3 has a two-carbon chain in which C 1 and C 2 are each bonded to two hydrogen atoms and a chlorine atom, respectively. The fourth compound labeled 4 has a two-carbon chain in which C 1 is bonded to three hydrogen atoms, and C 2 is bonded to three chlorine atoms.

A) I and II

B) II and III

C) III and IV

D) I and IV

E) II and IV

Diff: 2

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

10) Identify three constitutional isomers having the molecular formula C4H8BrCl.

An illustration shows the structure of five compounds. The first compound labeled 1 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 is bonded to two hydrogen atoms, C 3 is bonded to a bromine atom and a hydrogen atom, and C 4 is bonded to two hydrogen atoms and a chlorine atom. The second compound labeled 2 has a four-carbon chain in which C 1 and C 4 are each bonded to three hydrogen atoms; respectively, C 2 and C 3 are each bonded to a bromine atom and a hydrogen atom, respectively. The third compound labeled 3 has a four-carbon chain in which C 1 and C 4 are each bonded to three hydrogen atoms; respectively, C 2 is bonded to two hydrogen atoms, and C 3 is bonded to a bromine atom and a chlorine atom. The fourth compound labeled 4 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 is bonded to two hydrogen atoms, C 3 is bonded to a bromine atom and a hydrogen atom, and C 4 is bonded to two hydrogen atoms and a chlorine atom. The fifth compound labeled 5 has a four-carbon chain in which C 1 and C 4 are each bonded to three hydrogen atoms; respectively, C 2 is bonded to a chlorine atom and a hydrogen atom, and C 3 is bonded to a bromine atom and a hydrogen atom.

A) I, II, and III

B) II, III, and IV

C) III, IV, and V

D) I, III, and V

E) II, III, and V

Diff: 2

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

11) Identify three constitutional isomers having the molecular formula C4H8O.

An illustration shows the structure of five compounds. The first compound labeled 1 has a four-carbon chain in which C 1 is bonded to a hydrogen atom, C 1 is triple bonded to C 2, C 3 is bonded to two hydrogen atoms, C 4 is bonded to two hydrogen atoms and an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. The second compound labeled 2 has a four-carbon chain in which C 1 and C 3 are each bonded to two hydrogen atoms, C 1 is double bonded to C 2, C 2 is bonded to a hydrogen atom, and C 4 is bonded to two hydrogen atoms and an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. The third compound labeled 3 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 are each bonded to two hydrogen atoms; respectively, C 4 is double bonded to an oxygen atom carrying two lone pairs of electrons and single bonded to a hydrogen atom. The compound labeled 4 has a five-carbon chain in which C 1 and C 3 are each bonded to two hydrogen atoms; respectively, C 1 is double bonded to C 2, C 2 is bonded to a hydrogen atom, C 4 is replaced by an oxygen atom carrying two lone pairs of electrons, and C 5 is bonded to three hydrogen atoms. The fifth compound labeled 5 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 is bonded to are each bonded to two hydrogen atoms; respectively, and C 4 is bonded to two hydrogen atoms and an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom.

A) I, II, and III

B) II, III, and IV

C) III, IV, and V

D) I, II, and IV

E) II, III, and V

Diff: 2

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

12) What force is not considered in the formation of a covalent bond?

A) repulsion between two positively charged nuclei

B) force of attraction between positively charged nuclei and negatively charged electrons

C) repulsion between negatively charged electrons

D) repulsion between positively charged nuclei and negatively charged electrons

E) the distance between the atoms' nuclei

Diff: 1

Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair

13) What is the correct Lewis dot structure for the sulfur atom, S?

An illustration shows five Lewis dot structures. The first structure labeled 1 has a sulfur atom carrying four lone pairs of electrons. The second structure labeled 2 has a sulfur atom carrying two lone pairs of electrons. The third structure labeled 3 has a sulfur atom carrying two lone pairs of electrons and two valence electrons. The fourth structure labeled 4 has a sulfur atom carrying a lone pair of electrons and three valence electrons. The fifth structure labeled 5 has a sulfur atom carrying four valence electrons.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair

14) What is the correct Lewis dot structure for the carbon atom, C?

An illustration shows five Lewis dot structures. The first structure labeled 1 has a carbon atom carrying four lone pairs of electrons. The second structure labeled 2 has a carbon atom carrying three valence electrons. The third structure labeled 3 has a carbon atom carrying two lone pairs of electrons and two valence electrons. The fourth structure labeled 4 has a carbon atom carrying a lone pair of electrons and three valence electrons. The fifth structure labeled 5 has a carbon atom carrying four valence electrons.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair

15) What is the correct Lewis structure for the molecule shown in the box below?

An illustration shows P H 3, enclosed within a box. An illustration below shows five Lewis dot structures. The first structure labeled 1 has a central phosphorus atom carrying a lone pair of electrons bonded to three hydrogen atoms. The second structure labeled 2 has a phosphorus atom carrying two lone pairs bonded to a hydrogen atom on the left and a hydrogen atom on the right which is further bonded to another hydrogen atom. The third structure labeled 3 has a central hydrogen atom which is bonded to three phosphorus atoms each carrying three lone pairs of electrons, respectively. The fourth compound labeled 4 has a phosphorus atom which is bonded to three hydrogen atoms. The fifth compound labeled 5 has a cyclobutane ring in which C 1 is replaced by a phosphorus atom carrying two lone pairs of electrons, C 2, C 3, and C 4 are each replaced by a hydrogen atom, respectively.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair

16) What is the correct Lewis structure for the molecule shown in the box below?

An illustration shows C O C l 2 enclosed within a box. An illustration below shows five Lewis dot structures. The first structure labeled 1 has a chlorine atom carrying three lone pairs of electrons bonded to a carbon atom carrying a lone pair of electrons which is further bonded to an oxygen atom carrying two lone pairs of electrons which is further bonded to a chlorine atom carrying three lone pairs of electrons. The second structure labeled 2 has a central chlorine atom double bonded to an oxygen atom carting two lone pairs of electrons and single bonded to two chlorine atoms each carrying three lone pairs of electrons, respectively. The third structure labeled 3 has a central oxygen atom carrying a lone pair of electrons bonded to a carbon atom carrying a lone pair of electrons, and two chlorine atoms each carrying three lone pairs of electrons, respectively. The fourth structure labeled 4 has a central oxygen atom carrying a lone pair of electrons double bonded to a carbon atom carrying a lone pair of electrons and single bonded to two chlorine atoms each carrying three lone pairs of electrons, respectively. The fifth structure labeled 5 has a central carbon atom bonded to an oxygen atom carrying two lone pairs of electrons, and two chlorine atoms each carrying three lone pairs of electrons, respectively.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair

17) What is the correct Lewis structure for the molecule shown in the box below?

An illustration shows the molecule C H 3 C O 2 H enclosed within a box. An illustration below shows five Lewis dot structures. The first structure labeled 1 has carbon atom bonded to three hydrogen atoms and another carbon atom carrying a lone pair of electrons which is further bonded to an oxygen atom carrying two lone pairs of electrons which is bonded to another oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. The second structure labeled 2 has a carbon atom bonded to three hydrogen atoms of which one is further bonded to another carbon atom which is double bonded to an oxygen atom carrying two lone pairs of electrons and single bonded to another oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. The third structure labeled 3 has a carbon atom bonded to three hydrogen atoms and an oxygen atom carrying two lone pairs of electrons which is further bonded to another oxygen atom carrying two lone pairs of electrons which is bonded to a carbon atom carrying a lone pair of electrons which is further bonded to a hydrogen atom. The fourth structure labeled 4 has a carbon atom bonded to three hydrogen atoms and another carbon atom which is double bonded to an oxygen atom carrying two lone pairs of electrons and single bonded to another oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. The fifth structure labeled 5 has a carbon atom bonded to three hydrogen atoms and another carbon atom carrying a lone pair of electrons which is further double bonded to an oxygen atom carrying two lone pairs of electrons which is further bonded to another oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair

18) Which of the following compounds has two lone pairs on the central atom?

A) CO2

B) SCl2

C) NF3

D) CS2

E) SO3

Diff: 2

Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair

19) What is the formal charge on oxygen in the following structure?

An illustration shows the structure of a compound. It has a carbon atom which is bonded to three hydrogen atoms and an oxygen atom carrying a lone pair of electrons which is further bonded to two hydrogen atoms.

A) 2-

B) 1-

C) 2+

D) 1+

E) 0

Diff: 1

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

20) What is the formal charge on nitrogen in the following structure?

An illustration shows the structure of a compound. It has a carbon atom bonded to a hydrogen atom, double bonded to a nitrogen atom which is further bonded to two hydrogen atoms, and bonded to another carbon atom which is further bonded to three hydrogen atoms.

A) 2-

B) 1-

C) 2+

D) 1+

E) 0

Diff: 1

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

21) What is the formal charge on oxygen in the following structure?

An illustration shows the structure of a compound. It has a carbon atom double bonded to an oxygen atom carrying a lone pair of electrons which is further bonded to a hydrogen atom, and bonded to two methyl groups.

A) 0

B) 1+

C) 2+

D) 1-

E) 2-

Diff: 1

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

22) What is the formal charge on oxygen in the following structure?

An illustration shows the structure of a compound. It has a central oxygen atom carrying a lone pair of electrons. The oxygen atom is further bonded to a carbon atom on either side, in which the carbon atom is further bonded to three hydrogen atoms.

A) 2+

B) 2-

C) 1+

D) 1-

E) 0

Diff: 1

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

23) Which of the following structures have a formal charge of zero on the carbon atom?

An illustration shows the structure of four compounds. The first compound labeled 1 has a carbon atom bonded to three hydrogen atoms. The second compound labeled 2 has a carbon atom carrying a lone pair of electrons bonded to three hydrogen atoms. The third compound labeled 3 has a carbon atom carrying a valence electron bonded to three hydrogen atoms. The fourth compound labeled 4 has a carbon atom carrying a lone pair of electrons which is bonded to two hydrogen atoms.

A) I and III

B) II and III

C) III and IV

D) I and IV

E) II and IV

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

24) Which of the following structures have a 1- formal charge on the sulfur atom?

An illustration shows the structure of five compounds. The first compound labeled 1 has a central carbon atom bonded to three hydrogen atoms and sulfur atom carrying three lone pairs of electrons. The second compound labeled 2 has a central sulfur atom carrying two lone pairs of electrons bonded to two methyl groups. The third compound labeled 3 has a sulfur atom carrying a lone pair of electrons double bonded to an oxygen atom carrying two lone pairs of electrons and single bonded to another oxygen atom carrying three lone pairs of electrons. The fourth compound labeled 4 has a central carbon bonded to three hydrogen atoms and a sulfur atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. The fifth compound labeled 5 has a central sulfur atom bonded to two four oxygen atoms in which two carry three lone pairs of electrons, and two others carry two lone pairs of electrons and are each bonded to a hydrogen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

25) Which of the following structures have a 1+ formal charge on the sulfur atom?

An illustration shows the structure of five compounds. The first compound labeled 1 has a central carbon atom bonded to three hydrogen atoms and a sulfur atom carrying three lone pairs of electrons. The second compound labeled 2 has a central sulfur atom carrying two lone pairs of electrons bonded to two methyl groups. The third compound labeled 3 has a sulfur atom carrying a lone pair of electrons double bonded to an oxygen atom carrying two lone pairs of electrons and single bonded to another oxygen atom carrying three lone pairs of electrons. The fourth compound labeled 4 has a central carbon bonded to three hydrogen atoms and a sulfur atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. The fifth compound labeled 5 has a central sulfur atom bonded to two four oxygen atoms in which two carry three lone pairs of electrons, and two others carry two lone pairs of electrons and are each bonded to a hydrogen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

26) What are the formal charges on boron and nitrogen in the following structure?

An illustration shows the structure of a compound. It has a central boron atom bonded to three fluorine atoms each carrying three lone pairs of electrons, respectively. The boron atom is further bonded to a nitrogen atom, which is further bonded to three hydrogen atoms.

A) B = 1+, N = 1+

B) B = 1+, N = 1-

C) B = 1-, N = 1-

D) B = 1-, N = 1+

E) B = 1-, N = 0

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

27) What are the formal charges on boron and oxygen in the following structure?

An illustration shows the structure of a compound. It has a central oxygen atom carrying a lone pair of electrons bonded to two methyl groups and a boron atom which is further bonded to three fluorine atoms each carrying three lone pairs of electrons, respectively.

A) B = 1-, O = 1-

B) B = 1-, O = 1+

C) B = 1+, O = 1+

D) B = 1+, O = 1-

E) B = 1-, O = 0

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

28) Which of the following structures have 1+ formal charge on the central atom?

An illustration shows the structure of five compounds. The first compound labeled 1 has a central beryllium atom carrying two lone pairs of electrons bonded to two hydrogen atoms on both sides. The second compound labeled 2 has a central boron atom carrying four lone pairs of electrons bonded to four hydrogen atoms. The third compound labeled 3 has a nitrogen atom carrying four lone pairs of electrons bonded to three hydrogen atoms. The fourth compound labeled 4 has a nitrogen atom carrying four lone pairs of electrons bonded to four hydrogen atoms. The fifth compound labeled 5 has an oxygen atom carrying four lone pairs of electrons bonded to three hydrogen atoms.

A) I

B) II

C) III

D) III and V

E) IV and V

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

29) Which of the following structures have a formal charge on at least one atom?

An illustration shows the structures of five compounds. The first compound labeled 1 has a hydrogen atom bonded to a nitrogen atom carrying two lone pairs of electrons which is further bonded to a fluorine atom carrying three lone pairs of electrons. The second compound labeled 2 has two oxygen atoms carrying two lone pairs of electrons bonded to each other, each oxygen atom is further bonded to a hydrogen atom, respectively. The third compound labeled 3 has a central carbon atom bonded to three hydrogen atoms and a fluorine atom carrying three lone pairs of electrons. The fourth compound labeled 4 has a boron atom bonded to three oxygen atoms each carrying two lone pairs of electrons and bonded to a hydrogen atom, respectively. The fifth compound has a sulfur atom carrying two lone pairs of electrons bonded to two methyl groups.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

30) Which of the following structures have a 1— formal charge on the nitrogen atom?

An illustration shows the structures of five compounds. The first compound labeled 1 has a central nitrogen atom carrying a lone pair of electrons bonded to a hydrogen atom and two methyl groups. The second compound labeled 2 has a central nitrogen atom carrying two lone pairs of electrons bonded to two methyl groups. The third compound labeled 3 has a nitrogen atom carrying a lone pair of electrons bonded to two hydrogen atoms and a methyl group. The fourth compound labeled 4 has a nitrogen atom carrying a lone pair of electrons bonded to a methyl group and double bonded to a carbon atom which is further bonded to two hydrogen atoms. The fifth compound labeled 5 has a hydrogen atom bonded to an oxygen atom carrying two lone pairs of electrons, which is further bonded to a nitrogen atom carrying a lone pair of electrons, which is further bonded to two hydrogen atoms.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

31) The bonding pattern of oxygen with a formal charge of 1— could be described as ________.

A) one lone pair of electrons and three single bonds

B) two lone pairs of electrons and two single bonds

C) three lone pairs of electrons, and one single bond

D) one lone pair of electrons, one single, and one double bond

E) zero lone pairs, and two single and one double bond

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

32) What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

An illustration shows an H N O 3 group enclosed within a box. An illustration below shows the structures of five compounds. The first compound labeled 1 has a central nitrogen atom double bonded to an oxygen atom carrying three lone pairs of electrons, double bonded to an oxygen atom carrying two lone pairs of electrons, and single bonded to an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. The second compound labeled 2 has a central nitrogen atom bonded to two oxygen atoms each carrying three lone pairs of electrons and a negative charge, double bonded to another oxygen atom carrying two lone pairs of electrons and a positive charge which is further bonded to a hydrogen atom. The third compound labeled 3 has a nitrogen atom carrying a lone pair of electrons bonded to a hydrogen atom and two oxygen atoms each carrying three lone pairs of electrons and a negative charge. The fourth compound labeled 4 has a nitrogen atom carrying a positive charge double bonded to an oxygen atom carrying two lone pairs of electrons, bonded to an oxygen atom carrying three lone pairs of electrons and a negative charge, and bonded to another oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. The fifth compound labeled 5 has a nitrogen atom carrying a positive charge bonded to a hydrogen atom and three oxygen atoms each carrying three lone pairs of electrons and a negative charge, respectively.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

33) What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

An illustration shows H C N enclosed within a box. An illustration below shows the structure of five compounds. The first compound labeled 1 has a hydrogen atom bonded to a carbon atom carrying a positive charge which is further double bonded to a nitrogen atom carrying two lone pairs of electrons. The second compound labeled 2 has a hydrogen atom bonded to a carbon atom which is triple bonded to a nitrogen atom carrying a lone pair of electrons. The third compound labeled 3 has a hydrogen atom double bonded to a carbon atom which is further double bonded to a nitrogen atom carrying a lone pair of electrons and a positive charge. The fourth compound labeled 4 has a hydrogen atom bonded to a carbon atom carrying a lone pair of electrons and a negative charge which is further double bonded to a nitrogen atom carrying a lone pair of electrons. The fifth compound labeled 5 has a hydrogen atom double bonded to a carbon atom which is further double bonded to a nitrogen atom carrying a lone pair of electrons and a valence electron.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

34) What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

An illustration shows S C N enclosed within square brackets with a superscript minus charge. The structure is enclosed within a box. Another illustration shows the structure of five compounds. The first compound labeled 1 has a sulfur atom carrying three lone pairs of electrons bonded to a carbon atom which is further triple bonded to a nitrogen atom carrying a lone pair of electrons. The second compound labeled 2 has a sulfur atom carrying two lone pairs of electrons double bonded to a carbon atom which is further bonded to a nitrogen atom carrying three lone pairs of electrons. The third compound labeled 3 has a sulfur atom carrying two lone pairs of electrons double bonded to a carbon atom carrying a negative charge which is further triple bonded to a nitrogen atom carrying a lone pair of electrons. The fourth compound labeled 4 has a sulfur atom bonded to two lone pairs of electrons double bonded to a carbon atom which is bonded to a nitrogen atom carrying three lone pairs of electrons and a negative charge. The fifth compound labeled 5 has a sulfur atom carrying three lone pairs of electrons and a negative charge bonded to a carbon atom carrying a positive charge which is further triple bonded to a nitrogen atom carrying a lone pair of electrons.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

35) What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

Another illustration shows N O 2 enclosed within a box. An illustration shows the structure of five compounds. The first compound labeled 1 has a nitrogen atom carrying two lone pairs of electrons double bonded to a nitrogen atom carrying a positive charge which is further double bonded to an oxygen atom carrying two lone pairs of electrons. The second compound labeled 2 has a nitrogen atom carrying a lone pair of electrons tripe bonded to another nitrogen atom carrying a positive charge which is further bonded to an oxygen atom carrying three lone pairs of electrons and a negative charge. The third compound labeled 3 has a nitrogen atom carrying two lone pairs of electrons double bonded to another nitrogen atom which is further triple bonded to an oxygen atom carrying a lone pair of electrons. The fourth compound labeled 4 has a nitrogen atom carrying three lone pairs of electrons double bonded to another nitrogen atom carrying a lone pair of electrons which is further bonded to an oxygen atom carrying three lone pairs of electrons and a negative charge. The fifth compound labeled 5 has a nitrogen atom carrying three lone pairs of electrons and a negative charge bonded to another nitrogen atom carrying a positive charge which is further triple bonded to an oxygen atom carrying a lone pair of electrons.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

36) What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

An illustration shows H N 3 enclosed within a box. Another illustration shows the structure of five compounds. The first compound labeled 1 has a hydrogen atom bonded to a nitrogen atom carrying a lone pair of electrons which is further double bonded to another nitrogen atom carrying a positive charge which is further double bonded to another nitrogen atom carrying two lone pairs of electrons and a negative charge. The second compound labeled 2 has a hydrogen atom bonded to a nitrogen atom carrying a positive charge triple bonded to another nitrogen atom which is further bonded to a nitrogen atom carrying three lone pairs of electrons and a negative charge. The third compound labeled 3 has a hydrogen atom bonded to a nitrogen atom carrying two lone pairs of electrons which is further double bonded to a nitrogen atom which is further triple bonded to another nitrogen atom carrying a lone pair of electrons. The fourth compound labeled 4 has a hydrogen atom bonded to a nitrogen atom carrying a lone pair of electrons which is further double bonded to another nitrogen atom carrying a lone pair of electrons which is further bonded to another nitrogen atom carrying three lone pairs of electrons and a negative charge. The fifth compound labeled 5 has a hydrogen atom bonded to a nitrogen atom carrying two lone pairs of electrons and a negative charge which is further bonded to another nitrogen atom which is further triple bonded to a nitrogen atom carrying a lone pair of electrons and a positive charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

37) Which of the following bond-line structures are of the same compound?

An illustration shows the structure of four compounds. The compound labeled 1 has a SMILES string of CC1CCC(C1)C. The compound labeled 2 has a SMILES string of CCC1CCCC1. The compound labeled 3 has a SMILES string of CC1CCCC1C. The compound labeled 4 has a SMILES string of CCC1CCCC1 in which C 3 is bonded to a two-carbon chain.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

38) Which of the following bond-line structures represent the same compound?

An illustration shows the structure of four compounds. The compound labeled 1 has a SMILES string of CCCCC. The compound labeled 2 has a SMILES string of CCCC(C)C. The compound labeled 3 has a SMILES string of CCCCC where C 4 is bonded to a methyl group. The compound labeled 4 has a SMILES string of CCC(C)C.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

39) The electronegativity of elements on the periodic table tends to increase ________.

A) from left to right, top to bottom

B) from right to left, bottom to top

C) from left to right, bottom to top

D) from right to left, top to bottom

E) from upper right to lower left

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

40) Which of the following is the least electronegative element?

A) B

B) C

C) N

D) O

E) F

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

41) Which of the following is the most electronegative element?

A) B

B) C

C) N

D) O

E) H

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

42) Which of the following is the least electronegative element?

A) P

B) N

C) Na

D) Si

E) K

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

43) Which of the following is the most electronegative element?

A) P

B) N

C) S

D) O

E) F

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

44) What is the correct order of increasing electronegativity for Rb, F and O?

A) Rb < F < O

B) Rb < O < F

C) O < F < Rb

D) F < Rb < O

E) O < Rb < F

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

45) Which of the following series has the correct order of elements in increasing electronegativity?

A) C < N < B < Br

B) P < N < As < F

C) Li < B < N < F

D) Cl < Cs < C < Co

E) Be < B < Ba < Br

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

46) The Cl–Cl bond is best described as ________.

A) nonpolar covalent

B) polar covalent

C) ionic

D) coordinate covalent

E) None of these.

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

47) The C–Cl bond is best described as ________.

A) nonpolar covalent

B) polar covalent

C) ionic

D) coordinate covalent

E) None of these.

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

48) The bond between potassium and oxygen is best described as ________.

A) nonpolar covalent

B) polar covalent

C) ionic

D) coordinate covalent

E) None of these.

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

49) The bond between carbon and hydrogen is best described as ________.

A) nonpolar covalent

B) polar covalent

C) ionic

D) coordinate covalent

E) None of these.

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

50) Which of the following is the correct depiction of the dipole moment for a C–F bond?

The illustration shows five compounds with their dipole moments depicted. The first compound labeled 1 has a carbon atom bonded to a fluorine atom. A dipole moment arrow along the single bond points toward the fluorine atom. The second compound labeled 2 has a carbon atom bonded to a fluorine atom. A dipole moment arrow along the single bond points toward the carbon atom. The third compound labeled 3 has a carbon atom bonded to a fluorine atom. A dipole moment arrow points upward from the single bond. The fourth compound labeled 4 has a carbon atom bonded to a fluorine atom. A dipole moment arrow points downward from the single bond. The fifth compound labeled 5 has a carbon atom bonded to a fluorine atom. Two dipole moment arrows along the single bond point at each other.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

51) Which of the following illustrates the correct placement of partial charges for a P–Cl bond?

The illustration shows five compounds with their partial charges depicted. The first compound labeled 1 has a phosphorus atom carrying a partial positive charge bonded to a chlorine atom carrying a partial positive charge. The second compound labeled 2 has a phosphorus atom carrying a partial negative charge bonded to a chlorine atom carrying a partial positive charge. The third compound labeled 3 has a phosphorus atom carrying a partial positive charge bonded to a chlorine atom carrying a partial negative charge. The fourth compound labeled 4 has a phosphorus atom carrying a partial negative charge bonded to a chlorine atom carrying a partial negative charge. The fifth compound labeled 5 has a phosphorus atom carrying a partial charge bonded to a chlorine atom carrying a partial charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

52) Which of the following is the correct representation of partial charges at the indicated atoms?

An illustration shows the structure of a compound. It has a central carbon atom double bonded to an oxygen atom carrying two lone pairs of electrons, single bonded to a carbon atom further bonded to two hydrogen atoms and a chlorine atom carrying three lone pairs of electrons, and another carbon atom which is further bonded to three hydrogen atoms. An arrow labeled 1, points toward the chlorine atom. An arrow labeled 2 points toward an oxygen atom. An arrow labeled 3 points toward the central carbon atom.

A) I = δ+; II = δ+; III = δ+

B) I = δ—; II = δ—; III = δ—

C) I = δ+; II = δ+; III = δ—

D) I = δ—; II = δ—; III = δ+

E) I = δ+; II = δ—; III = δ+

Diff: 2

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

53) Which atom has the largest δ+ in the following compound?

An illustration shows the structure of a compound. It has a central carbon atom bonded to a hydrogen atom, two bromine atoms each carrying three lone pairs of electrons, and a nitrogen atom carrying a lone pair of electrons which is further double bonded to an oxygen atom carrying two lone pairs of electrons.

A) N

B) O

C) Br

D) H

E) C

Diff: 2

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

54) Which of the following statements best describes the C–Cl bond in the following compound?

An illustration shows the structure of a compound. It has a central carbon atom bonded to two hydrogen atoms, a carbon atom further bonded to two hydrogen atoms and a chlorine atom carrying three lone pairs of electrons, and another carbon atom which is further bonded to three hydrogen atoms.

A) nonpolar; no dipole

B) polar; δ+ at carbon and δ— at chlorine

C) polar; δ— at carbon and δ+ at chlorine

D) polar; δ— at carbon and δ— at chlorine

E) ionic

Diff: 2

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

55) Which of the following compounds have both polar covalent and ionic bonds?

A) NH4Br

B) H2O2

C) HCN

D) H2S

E) CH4

Diff: 2

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

56) How many hydrogen atoms are connected to the indicated carbon atom?

An illustration shows the structure of a compound. It has a five-carbon chain in which C 2 is bonded to two methyl groups. An arrow points toward C 2.

A) one

B) two

C) three

D) four

E) none

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

57) How many hydrogen atoms are connected to the indicated carbon atom?

An illustration shows the structure of a compound. It has a five-carbon chain in which C 2 is bonded to a methyl group. An arrow points toward C 2.

A) one

B) two

C) three

D) four

E) none

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

58) For NaOCH3, identify each bond as polar covalent, nonpolar covalent or ionic.

A) NaO = polar covalent; OC = polar covalent; CH = nonpolar covalent

B) NaO = ionic; OC = polar covalent; CH = nonpolar covalent

C) NaO = ionic; OC = ionic; CH = nonpolar covalent

D) NaO = polar covalent; OC = nonpolar covalent; CH = polar covalent

E) NaO = polar covalent; OC = nonpolar covalent; CH = nonpolar covalent

Diff: 2

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

59) For the following compound, identify the polar covalent bond(s) from the options provided.

An illustration shows the structure of a compound. It has a central carbon atom double bonded to an oxygen atom carrying two lone pairs of electrons, single bonded to a hydrogen atom and a carbon atom which is further bonded to two hydrogen atoms and a chlorine atom carrying three lone pairs of electrons respectively. An arrow labeled 1, points toward the double between the central carbon atom and the oxygen atom. An arrow labeled 2 points toward the bond between the two carbon atoms. An arrow labeled 3 points toward the bond between the carbon atom and the chlorine atom.

A) I and II

B) II and III

C) I and III

D) I only

E) II only

Diff: 2

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds

60) Orbitals with the same energy are called ________.

A) quantum orbitals

B) atomic orbitals

C) antibonding orbitals

D) bonding orbitals

E) degenerate orbitals

Diff: 1

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

61) What is the letter designation for the following atomic orbital?

An illustration shows a dumbbell shaped structure in which the upper lobe is shaded.

A) s

B) p

C) d

D) f

E) g

Diff: 1

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

62) How many hydrogen atoms are connected to the indicated carbon atom?

An illustration shows a cyclohexane ring. An arrow points toward C 2 of the compound.

A) one

B) two

C) three

D) four

E) none

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

63) In quantum mechanics a node (nodal surface or plane) is the ________.

A) location where ψ is negative

B) location where ψ is positive

C) location where ψ2 is positive

D) location where ψ2 is negative

E) location where ψ is zero

Diff: 2

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

64) Which of the following principle states that "Each orbital can accommodate a maximum of two electrons with opposite spin"?

A) Aufbau principle

B) Pauli exclusion principle

C) Hund's Rule

D) Heizenberg Uncertainty principle

E) Le Chatelier's principle

Diff: 1

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

65) Which of the following principle states "When orbitals of equal energy are available, every orbital gets one electron before any gets two electrons"?

A) Aufbau principle

B) Pauli exclusion principle

C) Hund's Rule

D) Heizenberg Uncertainty principle

E) Le Chatelier's principle

Diff: 1

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

66) Which of the following represents the ground state electron configuration for a phosphorous atom?

A) 1s22s22p63s13p4

B) 1s22s22p63s23p4

C) 1s22s22p63s23p3

D) 1s22s22p63s23p2

E) 1s22s22p63s23p5

Diff: 2

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

67) The atomic number for nitrogen is 7. Which of the following represents the ground state electron configuration for a nitrogen atom?

A) 1s22s12p4

B) 1s22p5

C) 2s22p5

D) 1s22s2 2p3

E) 1s22s23s3

Diff: 2

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

68) Which element has the ground state electron configuration of 1s22s22p63s23p5?

A) oxygen

B) fluorine

C) sulfur

D) chlorine

E) bromine

Diff: 2

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

69) Which element has the ground state electron configuration of 1s22s22p63s23p4?

A) Cl

B) S

C) P

D) Al

E) N

Diff: 2

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

70) What is the electronic configuration for the magnesium ion with a 2+ charge?

A) 1s22s22p63s2

B) 1s22s22p6

C) 1s22s22p4

D) 1s22s22p63s1

E) 1s22s22p63s22p2

Diff: 2

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

71) Which element has the following electronic configuration?

An illustration shows 1 s, 2 s, and 2 p orbitals. The 1 s and 2 s orbitals each have a pair of electrons with opposite spins. The three orbitals of 2 p each have an unpaired electron with an upward spin.

A) boron

B) carbon

C) silicon

D) nitrogen

E) fluorine

Diff: 2

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

72) Which element has the following electronic configuration?

An illustration shows 1 s, 2 s, and 2 p orbitals. The 1 s and 2 s orbitals each have a pair of electrons with opposite spins. Two of the three orbitals of 2 p each have a pair of electrons with opposite spins. One of the remaining 2 p orbitals has an unpaired electron with an upward spin.

A) boron

B) carbon

C) silicon

D) nitrogen

E) fluorine

Diff: 2

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

73) The following ground state electron configuration violates ________.

An illustration shows 1 s, 2 s, and 2 p orbitals. The 1 s orbital has a pair of electrons with an opposite spin. The 2 s orbital also has a pair of electrons with an opposite spin. Two of the three orbitals of 2 p each have a pair of electrons with opposite spins. One of the remaining 2 p orbitals is empty.

A) the Aufbau principle

B) the Pauli Exclusion principle

C) Hund's Rule

D) Heisenberg's Uncertainty principle

E) None of these.

Diff: 1

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

74) The following ground state electron configuration violates ________.

An illustration shows 1 s, 2 s, and 2 p orbitals. The 1 s orbital has a pair of electrons with an opposite spin. The 2 s orbital has an unpaired electron having a positive spin. Two of the three orbitals of 2 p each have a pair of electrons with opposite spins. One of the remaining 2 p orbitals has an unpaired electron with a downward spin.

A) the Aufbau principle

B) the Pauli Exclusion principle

C) Hund's Rule

D) Heisenberg's Uncertainty principle

E) None of these.

Diff: 1

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

75) The following ground state electron configuration violates ________.

An illustration shows 1 s, 2 s, and 2 p orbitals. The 1 s orbital has a pair of electrons with opposite spins. The 2 s orbitals has a pair of electrons with an upward spin. One of the three orbitals of 2 p has a pair of electrons with an upward spin. Two of the remaining 2 p orbitals each have an unpaired electron with an upward spin, respectively.

A) the Aufbau principle

B) the Pauli Exclusion principle

C) Hund's Rule

D) Heisenberg's Uncertainty principle

E) None of these.

Diff: 1

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

76) Ar, K+, and Cl— have equal numbers of electrons, and are considered isoelectronic. Select the correct ground state electron configuration for them.

A) 1s22s22p63s23p6

B) 1s22s22p63s6

C) 1s22s22p23s23p5

D) 1s22s22p63s13p64s1

E) 1s22s22p63s23p2

Diff: 2

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

77) Constructive interference of waves results in ________.

A) a wave with smaller amplitude

B) a wave with larger amplitude

C) cancellation of both waves

D) formation of a node

E) Both C and D

Diff: 1

Learning Objective: 1.8 Define a bond in terms of valence bond theory

78) Destructive interference of waves results in ________.

A) a wave with smaller amplitude

B) a wave with larger amplitude

C) cancellation of both waves

D) formation of a node

E) Both C and D

Diff: 1

Learning Objective: 1.8 Define a bond in terms of valence bond theory

79) All single bonds can be classified as ________.

A) nonpolar covalent

B) polar covalent

C) ionic

D) sigma bonds

E) pi bonds

Diff: 1

Learning Objective: 1.8 Define a bond in terms of valence bond theory

80) Which bonding type has circular symmetry with respect to the bond axis?

A) sigma bond

B) pi bond

C) delta bond

D) covalent bond

E) ionic bond

Diff: 2

Learning Objective: 1.8 Define a bond in terms of valence bond theory

81) Which best describes the difference between valence bond theory and molecular orbital (MO) theory?

A) valence bond theory requires the linear combination of atomic orbitals

B) MO theory requires the linear combination of atomic orbitals

C) valence bond theory considers only individual atomic orbitals

D) Both A and B

E) Both B and C

Diff: 2

Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs

82) How many molecular orbitals are formed when the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs

83) Which molecular orbitals are formed when the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule?

A) two bonding molecular orbitals

B) only one bonding molecular orbital

C) one bonding molecular orbital and one antibonding molecular orbital

D) two antibonding molecular orbitals

E) only one antibonding orbital

Diff: 2

Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs

84) How are electrons distributed in the molecular orbitals when the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule?

A) two electrons in the bonding molecular orbital

B) one electron in the bonding molecular orbital, one electron in the non-bonding molecular orbital

C) one electron in the bonding molecular orbital, one electron in the antibonding molecular orbital

D) two electrons in the antibonding molecular orbital

E) two electrons in the non-bonding molecular orbital

Diff: 2

Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs

85) How many hydrogen atoms are connected to the indicated carbon atom?

An illustration shows a compound with a SMILES string of CCCC#C. An arrow points toward C 2.

A) one

B) two

C) three

D) four

E) none

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

86) How many hydrogen atoms are connected to the indicated carbon atom?

An illustration shows a compound with a SMILES string of Cc1ccccc1. An arrow points toward C 1.

A) one

B) two

C) three

D) four

E) none

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

87) According to molecular orbital theory the highest energy molecular orbital that is occupied with an electron is referred to as ________.

A) degenerate

B) antibonding

C) the LCAO

D) the LUMO

E) the HOMO

Diff: 1

Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs

88) According to molecular orbital theory the lowest energy molecular orbital that is not occupied by an electron is referred to as ________.

A) degenerate

B) antibonding

C) the LCAO

D) the LUMO

E) the HOMO

Diff: 1

Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs

89) Identify the incorrect statement in regards to the overlap of 1s atomic orbitals of two hydrogen atoms resulting in constructive interference?

A) a sigma bonding molecular orbital is formed

B) the bonding molecular orbital formed is lower in energy than the 1s atomic orbital

C) the bonding molecular orbital formed has a node between the atoms

D) the bonding molecular orbital formed has circular symmetry

E) a maximum of two electrons may occupy the bonding molecular orbital

Diff: 3

Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs

90) For the following chemical reaction, how many hydrogen atoms are added or lost?

An illustration shows a reaction. A reactant that has a SMILES string of CCCCC yields a product that has a SMILES string of CCC=CC.

A) one hydrogen atom added

B) two hydrogen atoms added

C) one hydrogen atom lost

D) two hydrogen atoms lost

E) no change in the number of hydrogen atoms

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

91) For the following chemical reaction, how many hydrogen atoms are added or lost?

An illustration shows a reaction. A reactant that has a SMILES string of C1CCC(=O)CC1 yields a product that has a SMILES string of C1CCC(CC1)O.

A) one hydrogen atom added

B) two hydrogen atoms added

C) one hydrogen atom lost

D) two hydrogen atoms lost

E) no change in the number of hydrogen atoms

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

92) Interaction of the following two atomic orbitals in the orientation shown results in what kind of molecular orbital?

An illustration shows two dumbbell shaped structures of 2 p orbitals in which the first lobe of both the structures is shaded, respectively. There is a plus sign between the structures.

A) a sigma bonding molecular orbital is formed

B) a pi bonding molecular orbital is formed

C) a sigma antibonding molecular orbital is formed

D) a pi antibonding molecular orbital is formed

E) destructive interference occurs so no molecular orbital is formed

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

93) Interaction of the following two atomic orbitals results in what kind of molecular orbital, in the orientation shown?

An illustration shows two dumbbell shaped structures of 2 p orbitals in which the first lobe of the first structure and the second lobe of the second structure are shaded, respectively. There is a plus sign between the structures.

A) a sigma bonding molecular orbital is formed

B) a pi bonding molecular orbital is formed

C) a sigma antibonding molecular orbital is formed

D) a pi antibonding molecular orbital is formed

E) constructive interference occurs so no molecular orbital is formed

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

94) What is the hybridization of the oxygen atom in the following compound?

An illustration shows the structure of a compound that has a central carbon atom bonded to three hydrogen atoms and an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom.

A) sp

B) sp2

C) sp3

D) sp3d

E) s2p

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

95) What is the hybridization of the carbon atom in CO2?

A) sp

B) sp2

C) sp3

D) sp3d

E) s2p

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

96) What is the hybridization of the nitrogen atom in the following compound?

An illustration shows the structure of a compound that has a central carbon atom bonded to three hydrogen atoms and a nitrogen atom carrying two lone pairs of electrons which is further bonded to two hydrogen atoms.

A) sp

B) sp2

C) sp3

D) sp3d

E) s2p

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

97) What is the hybridization of the boron atom in the following compound?

An illustration shows the structure of a compound that has a central boron atom which is bonded to three fluorine atoms each carrying three lone pairs of electrons, respectively.

A) sp

B) sp2

C) sp3

D) sp3d

E) s2p

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

98) What is the hybridization of the carbon (I) atom in the following compound?

An illustration shows the structure of a compound. It has a central carbon atom which is bonded to a hydrogen atom, a carbon atom which is further bonded to three hydrogen atoms, and double bonded to a nitrogen atom carrying a lone pair of electrons which is further bonded to a hydrogen atom. An arrow points toward the central carbon atom.

A) sp

B) sp2

C) sp3

D) sp3d

E) sp3d2

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

99) What is the hybridization of the nitrogen atom in the following compound?

An illustration shows the structure of a compound. It has a central carbon atom which is bonded to a hydrogen atom, a carbon atom which is further bonded to three hydrogen atoms, and double bonded to a nitrogen atom carrying a lone pair of electrons which is further bonded to a hydrogen atom.

A) sp

B) sp2

C) sp3

D) sp4

E) s2p

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

100) The lone pair of electrons on the nitrogen atom in the following compound are located in which atomic orbital?

An illustration shows the structure of a compound. It has a central carbon atom which is bonded to a hydrogen atom, a carbon atom which is further bonded to three hydrogen atoms, and double bonded to a nitrogen atom carrying a lone pair of electrons which is further bonded to a hydrogen atom.

A) sp2

B) sp3

C) sp

D) s

E) p

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

101) Which of the following structures have carbon with sp2 hybridization?

An illustration shows the structure of four compounds. The first compound labeled 1 has a central carbon atom carrying a positive charge bonded to three hydrogen atoms. The second compound labeled 2 has a central carbon atom carrying a lone pair of electrons and a negative charge bonded to three hydrogen atoms. The third compound labeled 3 has a central carbon atom bonded to four hydrogen atoms. The fourth compound labeled 4 has a carbon atom carrying a lone pair of electrons bonded to two hydrogen atoms.

A) I and II

B) III and IV

C) I and III

D) II and IV

E) I and IV

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

102) Which of the indicated carbon atoms are sp2 hybridized?

An illustration shows the structure of a compound. It has a five-carbon chain in which C 1 and C 3 are each bonded to two hydrogen atoms, C 1 is double bonded to C 2, C 2 is bonded to a hydrogen atom, C 4 is double bonded to an oxygen atom, and C 5 is bonded to three hydrogen atoms. An arrow labeled 1, points toward C 1, an arrow labeled 2 points toward C 3, an arrow labeled 3 points toward C 4, and an arrow labeled 4 points toward C 5.

A) I and II

B) III and IV

C) II and III

D) I and III

E) II and IV

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

103) What is the correct hybridization for the indicated carbon atoms in the following compound?

An illustration shows the structure of a compound. It has a seven-carbon chain in which C 1, C 5, and C 6 are each bonded to a hydrogen atom. C 1 is triple bonded to C 2. C 3 and C 4 are each bonded to two hydrogen atoms. C 5 is double bonded to C 6. C 7 is bonded to three hydrogen atoms. An arrow labeled 1, points toward C 2, an arrow labeled 2 points toward C 5, and an arrow labeled 3 points toward C 7.

A) I = sp3, II = sp2, III = sp

B) I = sp2, II = sp, III = sp2

C) I = sp, II = sp2, III = sp3

D) I = sp, II = sp2, III = sp

E) I = sp2, II = sp3, III = sp2

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

104) How many ssp2 sigma bonds are in the following compound?

An illustration shows the structure of a compound. It has a five-carbon chain in which C 1 is bonded to three hydrogen atoms. C 2, C 3, and C 4 are each bonded to a hydrogen atom. Double bonds are present between C 2 and C 3 and C 4 and C 5. C 5 is bonded to two hydrogen atoms.

A) 2

B) 3

C) 4

D) 5

E) 6

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

105) The C2–C3 bond in the following compound results from the overlap of which orbitals?

An illustration shows the structure of a compound. It has five carbon atoms in which C 1 is bonded to three hydrogen atoms. C 2 is double bonded to an oxygen atom carrying two lone pairs of electrons. C 3 and C 5 are each bonded to two hydrogen atoms. C 4 is double bonded to C 5. C 4 is bonded to a hydrogen atom.

A) spsp2

B) spsp3

C) sp2—sp2

D) sp2—sp3

E) sp3—sp2

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

106) The sigma bond in the C=C in the following compound results from the overlap of which orbitals?

An illustration shows the structure of a compound. It has five carbon atoms in which C 1 and C 3 are each bonded to two hydrogen atoms. C 1 is double bonded to C 2. C 2 is bonded to a hydrogen atom. C 4 is double bonded to an oxygen atom carrying two lone pairs of electrons. C 5 is bonded to three hydrogen atoms.

A) spsp2

B) spsp3

C) sp2—sp2

D) sp2—sp3

E) sp3—sp2

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

107) The C–C sigma bond in ethyne (H–C≡C–H) results from the overlap of which orbitals?

A) spsp

B) spsp3

C) sp2—sp2

D) sps

E) pp

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

108) How many pi bonds are present in the following compound?

An illustration shows the structure of a compound. It has five carbon atoms in which C 1 and C 3 are each bonded to two hydrogen atoms. C 1 is double bonded to C 2. C 2 is bonded to a hydrogen atom. C 4 is double bonded to an oxygen atom carrying two lone pairs of electrons. C 5 is bonded to three hydrogen atoms.

A) one

B) two

C) three

D) four

E) five

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

109) How many pi bonds are present in the following compound?

An illustration shows the structure of a compound. It has a benzene ring in which C 1, C 3, C 4, C 5, and C 6 are each bonded to a hydrogen atom. C 2 is bonded to a seven-carbon chain, in which C 1, C 4, and C 5 are each bonded to two hydrogen atoms. C 2 is double bonded to C 3. C 2, C 3 and C 7 are each bonded to a hydrogen atom. C 6 is triple bonded to C 7.

A) two

B) three

C) four

D) five

E) six

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

110) The sigma bond that is part of C=N in the following compound results from the overlap of which orbitals?

An illustration shows the structure of a compound. It has a central carbon atom bonded to a hydrogen atom, another carbon atom which is further bonded to three hydrogen atoms, and double bonded to a nitrogen atom carrying a lone pair of electrons which is further bonded to an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom.

A) sp2sp2

B) spsp

C) sp2—sp3

D) sp3—sp3

E) sp3—sp2

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

111) The bonds indicated by the arrow in the following compound results from the overlap of which orbitals?

An illustration shows the structure of a compound. It has a five-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 is triple bonded to C 3, C 4 is bonded to a hydrogen atom, C 5 is bonded to two hydrogen atoms, and C 4 is double bonded to C 5. An arrow points toward the double bonded between C 4 and C 5.

A) sp2sp2

B) sp3—sp3

C) pp

D) Both A and B

E) Both A and C

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

112) Which orbitals are involved in the C–O sigma bond in acetone, shown below?

An illustration shows the structure of a compound. It has a central carbon atom double bonded to an oxygen atom carrying two lone pairs of electrons bonded to two methyl groups.

A) Csp2–Osp2

B) Csp3–Osp3

C) Csp–Osp

D) Cp–Op

E) Csp–Op

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

113) Which of the following best describes the orbitals involved in the formation of the C=O bond in acetone, shown below?

An illustration shows the structure of a compound. It has a central carbon atom double bonded to an oxygen atom carrying two lone pairs of electrons bonded to two methyl groups.

A) σ = Csp2 - Osp2 and π = Csp2 - Osp2

B) σ = Csp2 - Osp2 and π = Cp - Op

C) σ = Csp3 - Osp2 and π = Cp - Op

D) σ = Cp - Op and π = Csp2 - Osp2

E) σ = Csp - Osp and π = Cp - Op

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

114) The C–H bond in the methyl cation, CH3+, results from the overlap of which orbitals?

A) sp3sp2

B) sp3—s

C) sp2s

D) sp3—p

E) ps

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

115) The lone pair of electrons in the methyl anion, :CH3–, resides in which orbital?

A) s2

B) p

C) sp

D) sp3

E) sp2

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

116) What is the hybridization of the indicated atoms in the following compound?

An illustration shows the structure of a compound. It has an oxygen atom carrying two lone pairs of electrons double bonded to a carbon atom which is further double bonded to a nitrogen atom carrying a lone pair of electrons which is further bonded to a carbon atom bonded to three hydrogen atoms. An arrow labeled 1, points toward the oxygen atom. An arrow labeled 2 points toward the carbon atom double bonded to the oxygen atom. An arrow labeled 3 points at the nitrogen atom. An arrow labeled 4 points at the carbon atom bonded to the nitrogen atom.

A) I = sp ; II = sp2 ; III = sp3 ; IV = sp2

B) I = sp2 ; II = sp ; III = sp2 ; IV = sp3

C) I = sp3 ; II = sp2 ; III = sp ; IV = sp2

D) I = sp2 ; II = sp3 ; III = sp2 ; IV = sp

E) I = sp2 ; II = sp2 ; III = sp2 ; IV = sp3

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

117) The carbon and oxygen atoms in carbon monoxide are connected by which type of bond(s)?

A) a sigma (σ) bond

B) two sigma (σ) bonds

C) a pi (π) bond

D) two pi (π) bonds

E) both A and D

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

118) The N–H bond in the following compound is a ________ and is formed from the ________.

An illustration shows a carbon atom which is bonded to three hydrogen atoms and a nitrogen atom carrying a lone pair of electrons which is further bonded to two hydrogen atoms.

A) σ bond; sp2 — s orbital overlap

B) σ bond; sp3 — s orbital overlap

C) π bond; sp3 — s orbital overlap

D) π bond; sp2 — p orbital overlap

E) π bond; pp orbital overlap

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

119) Identify the shortest bond in the following compound.

An illustration shows the structure of a compound. It has a five-carbon chain in which C 1 is bonded to two hydrogen atoms. C 1 is double bonded to C 2. C 2 is bonded to a hydrogen atom. C 3 is triple bonded to C 4. C 5 is bonded to three hydrogen atoms. An arrow labeled 1, points toward the double bond between C 1 and C 2. An arrow labeled 2 points toward the bond between C 2 and C 3. An arrow labeled 3 points toward the triple bond. An arrow labeled 4 points toward the bond between C 4 and C 5.

A) I

B) II

C) III

D) IV

E) I and III have the same length

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

120) Which of the following compounds has the shortest carbon—carbon bond?

An illustration shows the structure of four compounds. The first compound labeled 1 has a two-carbon chain in which C 1 and C 2 are each bonded to three hydrogen atoms, respectively. The second compound labeled 2 has a two-carbon chain in which C 1 and C 2 are double bonded to each other and are each bonded to two hydrogen atoms, respectively. The third compound labeled 3 has a three-carbon chain in which C 1 and C 3 are each bonded to three hydrogen atoms, respectively. C 2 is bonded to two hydrogen atoms. The fourth compound labeled 4 has a two-carbon chain in which C 1 is triple bonded to C 2 and each carbon atom is bonded to a hydrogen atom, respectively.

A) I

B) II

C) III

D) IV

E) All the carbon bonds are equal in length

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

121) Which of the statements best describes the carbon-carbon bond length and strength for the following compounds.

An illustration shows the structure of two compounds. The first compound labeled 1 has a two-carbon chain in which C 1 and C 2 are double bonded to each other and are each bonded to two hydrogen atoms, respectively. The second compound labeled 2 has a two-carbon chain in which C 1 is triple bonded to C 2 and each carbon atom is bonded to a hydrogen atom, respectively.

A) the shortest and strongest bond is found in compound I

B) the shortest and strongest bond is found in compound II

C) the shortest and weakest bond is found in compound I

D) the shortest and weakest bond is found in compound II

E) the shortest bond is found in compound I and the weakest bond in compound II

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

122) Identify the longest C–C bond(s) in the following compound?

An illustration shows the structure of a compound. It has a five-carbon chain in which C 1 is bonded to two hydrogen atoms. C 1 is double bonded to C 2. C 2 is bonded to a hydrogen atom. C 3 is triple bonded to C 4. C 5 is bonded to three hydrogen atoms. An arrow labeled 1, points toward the double bond between C 1 and C 2. An arrow labeled 2 points toward the triple bond between C 3 and C 4. An arrow labeled 3 points toward the bond between C 4 and C 5.

A) I

B) II

C) III

D) I and III

E) I and II

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

123) Rank the indicated C–C bonds in order of increasing bond length.

An illustration shows the structure of a compound. It has a five-carbon chain in which C 1 is bonded to two hydrogen atoms. C 1 is double bonded to C 2. C 2 is bonded to a hydrogen atom. C 3 is triple bonded to C 4. C 5 is bonded to three hydrogen atoms. An arrow labeled 1, points toward the double bond between C 1 and C 2. An arrow labeled 2 points toward the triple bond between C 3 and C 4. An arrow labeled 3 points toward the bond between C 4 and C 5.

A) I < II < III

B) II < III < I

C) III < I< II

D) II < I< III

E) I < III< II

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

124) Identify the compound with the strongest carbon — nitrogen bond.

A) CH3CH2CH=NH

B) CH3CH2NH2

C) CH3CH2C≡N

D) (CH3)3N

E) The strength of the carbon-nitrogen bonds are the same

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

125) Identify the compound with the longest carbon — nitrogen bond.

A) CH3CH2CH=NH

B) CH3CH2NH2

C) CH3CH2C≡N

D) CH3CH=NCH3

E) The length of all the carbon-nitrogen bonds are the same

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

126) What is the molecular geometry of the central atom in the following compound?

An illustration shows a C C l 4 enclosed within a box.

A) tetrahedral

B) trigonal planar

C) trigonal pyramidal

D) square planar

E) linear

Diff: 1

Learning Objective: 1.11 Describe VSEPR theory

127) Which of the following compound(s) have trigonal planar molecular geometry?

An illustration shows the structure of four compounds. The first compound labeled 1 has a central boron atom which is bonded to three fluorine atoms each carrying three lone pairs of electrons. The second compound labeled 2 has a central oxygen atom carrying a lone pair of electrons and a positive charge bonded to three hydrogen atoms. The third compound labeled 3 has a central carbon atom carrying a lone pair of electrons and a negative charge which is bonded to three hydrogen atoms. The fourth compound labeled 4 has a central nitrogen atom carrying a lone pair of electrons bonded to three fluorine atoms each carrying three lone pairs of electrons.

A) I

B) II

C) III

D) IV

E) I and IV

Diff: 1

Learning Objective: 1.11 Describe VSEPR theory

128) Which of the following compound(s) have trigonal pyramidal molecular geometry?

An illustration shows the structure of four compounds. The first compound labeled 1 has a central boron atom which is bonded to three fluorine atoms each carrying three lone pairs of electrons. The second compound labeled 2 has a central oxygen atom carrying two lone pairs of electrons bonded to two hydrogen atoms. The third compound labeled 3 has a central carbon atom bonded to four hydrogen atoms. The fourth compound labeled 4 has a central nitrogen atom carrying a lone pair of electrons bonded to three fluorine atoms each carrying three lone pairs of electrons.

A) I

B) II

C) III

D) IV

E) I and IV

Diff: 1

Learning Objective: 1.11 Describe VSEPR theory

129) Which of the following compound(s) have bent molecular geometry?

An illustration shows the structure of four compounds. The first compound labeled 1 has a central boron atom which is bonded to three fluorine atoms each carrying three lone pairs of electrons. The second compound labeled 2 has a central oxygen atom carrying two lone pairs of electrons bonded to two hydrogen atoms. The third compound labeled 3 has a central carbon atom bonded to four hydrogen atoms. The fourth compound labeled 4 has a central nitrogen atom carrying a lone pair of electrons bonded to three fluorine atoms each carrying three lone pairs of electrons.

A) I

B) II

C) III

D) IV

E) I and IV

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

130) Which of the following compound(s) have trigonal planar molecular geometry?

An illustration shows the structure of five compounds. The first compound labeled 1 has a central carbon atom carrying a lone pair of electrons and a negative charge bonded to three hydrogen atoms. The second compound labeled 2 has a central oxygen atom carrying a lone pair of electrons and a positive charge which is bonded to three hydrogen atoms. The third compound labeled 3 has a central boron atom bonded to three fluorine atoms each carrying three lone pairs of electrons. The fourth compound labeled 4 has a central oxygen atom carrying two lone pairs of electrons bonded to two hydrogen atoms. The fifth compound labeled 5 has a central carbon atom carrying a positive charge bonded to three hydrogen atoms.

A) I, II and III

B) II and III

C) III and V

D) V only

E) All of these

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

131) Which of the following compound(s) have a tetrahedral arrangement of electron pairs?

An illustration shows the structure of five compounds. The first compound labeled 1 has a central carbon atom carrying a lone pair of electrons and a negative charge bonded to three hydrogen atoms. The second compound labeled 2 has a central oxygen atom carrying a lone pair of electrons and a positive charge which is bonded to three hydrogen atoms. The third compound labeled 3 has a central boron atom bonded to three fluorine atoms each carrying three lone pairs of electrons. The fourth compound labeled 4 has a central oxygen atom carrying two lone pairs of electrons bonded to two hydrogen atoms. The fifth compound labeled 5 has a central nitrogen atom carrying a lone pair of electrons bonded to three hydrogen atoms.

A) I, II and III

B) I, II, IV and V

C) III and IV and V

D) IV and V

E) All of these

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

132) Which of the following compounds have trigonal planar arrangement of electron pairs?

An illustration shows the structure of five compounds. The first compound labeled 1 has a central carbon atom carrying a lone pair of electrons and a negative charge bonded to three hydrogen atoms. The second compound labeled 2 has a central sulfur atom carrying a lone pair of electrons double bonded to two oxygen atoms each carrying two lone pairs of electrons. The third compound labeled 3 has a central boron atom bonded to three fluorine atoms each carrying three lone pairs of electrons. The fourth compound labeled 4 has a central oxygen atom carrying two lone pairs of electrons bonded to two hydrogen atoms. The fifth compound labeled 5 has a central nitrogen atom carrying a lone pair of electrons bonded to three hydrogen atoms.

A) I, II and III

B) I, II, IV and V

C) III and IV and V

D) II and III

E) All of these

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

133) What is the molecular geometry at the central atom in in the molecule shown in the box?

An illustration shows a C H 2 B r 2 group enclosed within a box.

A) trigonal planar

B) trigonal pyramidal

C) square planar

D) tetrahedral

E) None of these

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

134) What is the molecular geometry at the central atom in the molecule shown in the box?

An illustration shows a C l 2 C O enclosed within a box.

A) trigonal planar

B) trigonal pyramidal

C) square planar

D) tetrahedral

E) bent

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

135) What is the molecular geometry at the nitrogen atom in the following compound?

An illustration shows the structure of a compound. It has a two-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 is bonded to a hydrogen atom, and double bonded to a nitrogen atom carrying a lone pair of electrons which is further bonded to an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom.

A) trigonal planar

B) trigonal pyramidal

C) linear

D) tetrahedral

E) bent

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

136) Which compound does not have a linear molecular geometry?

A) CO2

B) H2O

C) BeCl2

D) HCN

E) C2H2

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

137) What is the approximate bond angle around the indicated carbon atom?

An illustration shows the structure of a compound. It has a four-carbon chain in which C 1 and C 4 are each bonded to three hydrogen atoms, C 2 is bonded to two hydrogen atoms, and C 3 is double bonded to an oxygen atom carrying a lone pair of electrons and a positive charge which is further bonded to a hydrogen atom. An arrow points toward C 3.

A) 60°

B) 90°

C) 109.5°

D) 120°

E) 180°

Diff: 1

Learning Objective: 1.11 Describe VSEPR theory

138) What is the approximate bond angle around the indicated carbon atom?

An illustration shows a two-carbon chain in which C 1 is bonded to three hydrogen atoms, and C 2 is triple bonded to an oxygen atom carrying a lone pair of electrons and a positive charge. An arrow points toward C 2.

A) 60°

B) 90°

C) 109.5°

D) 120°

E) 180°

Diff: 1

Learning Objective: 1.11 Describe VSEPR theory

139) What is the approximate bond angle around the nitrogen atom?

An illustration shows a benzene ring in which C 1 is replaced by a nitrogen atom carrying a lone pair of electrons. C 2, C 3, C 4, C 5, and C 6 are each bonded to a hydrogen atom.

A) 90°

B) 109.5°

C) 120°

D) 180°

E) 100°

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

140) What is the approximate bond angle around the carbon atom in the following molecule?

An illustration shows C l 2 C O enclosed within a box.

A) 90°

B) 109.5°

C) 105°

D) 120°

E) 180°

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

141) What is the hybridization and approximate bond angle around the carbon atom in the following molecule?

An illustration shows an H C N enclosed within a box.

A) sp2, 120°

B) sp, 180°

C) sp3, 109.5°

D) sp3, 120°

E) sp, 120°

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

142) What is the hybridization state and approximate bond angle around nitrogen in the following compound?

An illustration shows the structure of a compound. It has a central nitrogen atom carrying a lone pair of electrons bonded to three carbon atoms which are each further bonded to three hydrogen atoms, respectively.

A) sp2, 109.5°

B) sp2, 107°

C) sp3, 109.5°

D) sp3, 107°

E) sp2, 120°

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

143) What is the hybridization state and approximate bond angle around oxygen in the following compound?

An illustration shows the structure of a compound. It has a central oxygen atom carrying two lone pairs of electrons bonded to two carbon atoms which are each further bonded to three hydrogen atoms, respectively.

A) sp, 109.5°

B) sp2, 109.5°

C) sp3, 109.5°

D) sp2, 120°

E) sp, 180°

Diff: 3

Learning Objective: 1.11 Describe VSEPR theory

144) What is the hybridization state and molecular geometry around the sulfur atom in the molecule shown in the box?

An illustration shows S O 3 enclosed within a box.

A) sp2, tetrahedral

B) sp2, trigonal planar

C) sp3, tetrahedral

D) sp3, trigonal pyramidal

E) sp2, trigonal pyramidal

Diff: 3

Learning Objective: 1.11 Describe VSEPR theory

145) What is the hybridization state and molecular geometry around the carbon atom in the molecule shown in the box?

An illustration shows C O 2 enclosed within a box.

A) sp, linear

B) sp2, trigonal planar

C) sp3, tetrahedral

D) sp3, trigonal pyramidal

E) sp2, trigonal pyramidal

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

146) Identify the hybridization state, molecular geometry and approximate bond angle for the species shown in box below.

An illustration shows a C H 3 group in which the carbon atom carries a positive charge. It is labeled methyl cation and is enclosed within a box.

A) sp2, tetrahedral, 109°

B) sp2, trigonal planar, 120°

C) sp3, tetrahedral, 109.5°

D) sp3, trigonal pyramidal, 120°

E) sp2, trigonal pyramidal, 180°

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

147) Identify the hybridization state, molecular geometry and approximate bond angle for the species shown in box below.

An illustration shows a C H 3 group in which the carbon atom carries a lone pair of electrons and negative charge. It is labeled methyl anion and is enclosed within a box.

A) sp2, tetrahedral, 109°

B) sp2, trigonal planar, 120°

C) sp3, tetrahedral, 109.5°

D) sp3, trigonal pyramidal, <109.5°

E) sp2, trigonal pyramidal, 180°

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

148) Identify the hybridization state, molecular geometry and approximate bond angle around the sulfur atom for the following molecule.

An illustration shows C l 2 S O enclosed within a box.

A) sp2, tetrahedral, 109°

B) sp2, trigonal planar, 120°

C) sp3, tetrahedral, 109.5°

D) sp3, trigonal pyramidal, <109.5°

E) sp2, trigonal pyramidal, 180°

Diff: 3

Learning Objective: 1.11 Describe VSEPR theory

149) Identify the hybridization state, molecular geometry and approximate bond angle around the carbon atom for the molecule shown in box below.

An illustration shows an H C O O H group enclosed within a box.

A) sp2, tetrahedral, 109°

B) sp2, trigonal planar, 120°

C) sp3, tetrahedral, 109.5°

D) sp3, trigonal pyramidal, <109.5°

E) sp2, trigonal pyramidal, 180°

Diff: 3

Learning Objective: 1.11 Describe VSEPR theory

150) Following is the structure for Propranolol, an antihypertensive drug. Identify the hybridization state, molecular geometry and approximate bond angle at the nitrogen atom in Propranolol.

An illustration shows the structure of a compound. It has two benzene rings fused together. All the carbon atoms except C 3 of the second benzene ring are each bonded to a hydrogen atom. C 3 of the second benzene ring is further bonded to a six-carbon chain in which C 1 is replaced by an oxygen atom carrying two lone pairs of electrons. C 2 and C 4 are each bonded to two hydrogen atoms. C 2 is bonded to a hydrogen atom and an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. C 5 is replaced by a nitrogen atom carrying a lone pair of electrons and is further bonded to a hydrogen atom. C 6 is bonded to a hydrogen atom and two methyl groups.

A) sp2, tetrahedral, 109°

B) sp2, trigonal planar, 120°

C) sp3, tetrahedral, 109.5°

D) sp3, trigonal pyramidal, ~109.5°

E) sp2, trigonal pyramidal, 180°

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

151) Identify the hybridization state, molecular geometry and approximate bond angle at the indicated nitrogen atom in the following compound.

An illustration shows the structure of a compound. It has a cyclohexane ring in which C 1 is bonded to a methyl group. C 3 and C 4 are each bonded to two hydrogen atoms; C 5 is replaced by a nitrogen atom carrying a positive charge and further bonded to a hydrogen atom. C 6 is bonded to a hydrogen atom. C 1 is double bonded to C 2. N 5 is double bonded to C 6. C 2 is bonded to a four-carbon chain in which C 1 is bonded to a hydrogen atom. C 2 is replaced by a nitrogen atom carrying a lone pair of electrons. C 1 is double bonded to the nitrogen atom. C 3 is bonded to a hydrogen atom and a methyl group. C 4 is double bonded to an oxygen atom carrying two lone pairs of electrons and single bonded to another oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. An arrow points toward the nitrogen atom carrying a lone pair of electrons.

A) sp2, bent, 109°

B) sp2, bent, 120°

C) sp3, tetrahedral, 109.5°

D) sp3, trigonal pyramidal, ~109.5°

E) sp2, trigonal pyramidal, 120°

Diff: 3

Learning Objective: 1.11 Describe VSEPR theory

152) Tryptophan is an essential amino acid that is important in the synthesis of the neurotransmitter serotonin. Identify the hybridization state, molecular geometry and approximate bond angle at the indicated carbon atom.

An illustration shows a compound that has a SMILES string of c1ccc2c(c1)c(c[nH]2)CC(C(=O)O)N. An arrow points toward C 5 of the cyclopentane ring.

A) sp2, tetrahedral, 109°

B) sp2, trigonal planar, 120°

C) sp3, tetrahedral, 109.5°

D) sp3, trigonal pyramidal, ~109.5°

E) sp2, trigonal pyramidal, 180°

Diff: 3

Learning Objective: 1.11 Describe VSEPR theory

153) Which of the following covalent bonds has the largest dipole moment?

A) C–C

B) C–H

C) C–O

D) N–H

E) H–F

Diff: 1

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

154) Which of the following compounds has no dipole moment?

A) CH4

B) NH3

C) HF

D) HCl

E) HBr

Diff: 1

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

155) Which of the following compounds has polar covalent bonds?

A) NH3

B) Na2O

C) H2

D) KF

E) CH4

Diff: 1

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

156) Which of the following compounds have a net dipole moment?

A) CBr4

B) CO2

C) CH4

D) H2O

E) C2H4

Diff: 2

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

157) Which of the following compounds does not have a dipole moment?

A) HCl

B) NCl3

C) CO

D) BF3

E) H2O

Diff: 2

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

158) Which of the following compounds has a net dipole moment of zero?

An illustration shows the structure of five compounds. The first compound labeled 1 has a two-carbon chain in which C 1 is double bonded to C 2, C 1 is bonded to a hydrogen atom at the top and a fluorine atom at the bottom, and C 2 is bonded to a fluorine atom at the top and a hydrogen atom at the bottom. The second compound labeled 2 has a two-carbon chain in which C 1 is double bonded to C 2, C 1 is bonded to two hydrogen atoms, and C 2 is bonded to two fluorine atoms. The third compound labeled 3 has a two-carbon chain in which C 1 is double bonded to C 2, and C 1 and C 2 are each bonded to a hydrogen atom on top and a fluorine atom at the bottom, respectively. The fourth compound labeled 4 has a two-carbon chain in which C 1 is double bonded to C 2, C 1 is bonded to a hydrogen atom and a fluorine atom, and C 2 is bonded to two fluorine atoms. The fifth compound labeled 5 has a two-carbon chain in which C 1 is double bonded to C 2, C 1 is bonded to a hydrogen atom and a fluorine atom, and C 2 is bonded to a chlorine atom and a hydrogen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

159) Identify the following compound(s) having a dipole moment?

An illustration shows the structure of 5 compounds. The first compound labeled 1 has a carbon atom double bonded to two oxygen atoms. The second compound labeled 2 has a carbon atom double bonded to an oxygen atom and nitrogen atom which is further bonded to a hydrogen atom. The third compound labeled 3 has a carbon atom double bonded to a sulfur atom and nitrogen atom which is further bonded to a hydrogen atom. The fourth compound labeled 4 has a carbon atom carrying a negative charge triple bonded to an oxygen atom carrying a positive charge.

A) II

B) III

C) II and III

D) I, II and III

E) II, III and IV

Diff: 2

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

160) Rank the following compounds in order of decreasing dipole moment.

An illustration shows the structure of three compounds. The first compound labeled 1 has a two-carbon chain in which C 1 is double bonded to C 2, C 1 is bonded to a hydrogen atom at the top and a fluorine atom at the bottom, and C 2 is bonded to a fluorine atom at the top and a hydrogen atom at the bottom. The second compound labeled 2 has a two-carbon chain in which C 1 is double bonded to C 2, C 1 is bonded to a hydrogen atom and a fluorine atom, and C 2 is bonded to two fluorine atoms. 
The third compound labeled 3 has a two-carbon chain in which C 1 is double bonded to C 2, and C 1 and C 2 are each bonded to a hydrogen atom on top and a fluorine atom at the bottom, respectively.

A) I > II > III

B) II > III > I

C) I > III > II

D) III > II > I

E) II > I > III

Diff: 3

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

161) Rank the following compounds in order of decreasing dipole moment.

An illustration shows the structure of three compounds. The first compound labeled 1 has a cyclohexane ring in which C 1 and C 3 are each double bonded to an oxygen atom carrying two lone pairs of electrons, and C 2, C 4, C 5, and C 6 are each bonded to two hydrogen atoms. The second compound labeled 2 has a cyclohexane ring in which C 1 and C 4 are each double bonded to an oxygen atom carrying two lone pairs of electrons, and C 2, C 3, C 5, and C 6 are each bonded to two hydrogen atoms. The third compound labeled 3 has a cyclohexane ring in which C 1 and C 2 are each double bonded to an oxygen atom carrying two lone pairs of electrons, and C 3, C 4, C 5, and C 6 are each bonded to two hydrogen atoms.

A) I > II > III

B) II >III > I

C) I > III > II

D) III > I > II

E) II > I > III

Diff: 2

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

162) For the following transformation, how many hydrogen atoms are added or lost?

An illustration shows a reaction. The reactant that has a SMILES sting of C=CCC=C yields a product that has a SMILES string of CCC#CC.

A) one hydrogen atom added

B) two hydrogen atoms added

C) one hydrogen atom lost

D) two hydrogen atoms lost

E) no change in the number of hydrogen atoms

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

163) For the following equation, how many hydrogen atoms are added or lost?

An illustration shows a reaction. The reactant that has the SMILES sting of C1CCOCC1 yields a product that has a SMILES string of C1CCOC(C1)O.

A) one hydrogen atom added

B) two hydrogen atoms added

C) one hydrogen atom lost

D) two hydrogen atoms lost

E) no change in the number of hydrogen atoms

Diff: 1

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

164) For the following equation, how many hydrogen atoms are added or lost?

A) one hydrogen atom added

B) two hydrogen atoms added

C) one hydrogen atom lost

D) two hydrogen atoms lost

E) no change in the number of hydrogen atoms

Diff: 2

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

165) Which of the intermolecular forces listed below is generally considered the strongest?

A) London dispersion forces

B) fleeting dipole-dipole interactions

C) dipole-dipole interactions

D) hydrogen bonding

E) the vital force

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

166) Which intermolecular force is generally considered the weakest?

A) ion-dipole interactions

B) London dispersion forces

C) dipole-dipole interactions

D) hydrogen bonding

E) covalent bonding

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

167) What is the strongest intermolecular force possible between molecules of the following structure?

An illustration shows the structure of a compound. It has a four-carbon chain in which C 1 is bonded to three hydrogen atoms. C 2 and C 3 are each bonded to two hydrogen atoms. C 4 is bonded to two hydrogen atoms and an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom.

A) ion-dipole interactions

B) London dispersion forces

C) dipole-dipole interactions

D) hydrogen bonding

E) covalent bonding

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

168) What is the strongest intermolecular force possible between molecules of the following structure?

An illustration shows the structure of a compound. It has a four-carbon chain in which C 1 is bonded to three hydrogen atoms. C 2 and C 3 are each bonded to two hydrogen atoms. C 4 is bonded to two hydrogen atoms and a sulfur atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom.

A) ion-dipole interactions

B) London dispersion forces

C) dipole-dipole interactions

D) hydrogen bonding

E) covalent bonding

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

169) Which of the following statements best explains the observation that hydrogen fluoride has the highest boiling point of all the hydrogen halides?

A) The fluorine in HF is the smallest atom for all of the halogens.

B) Fluorine is the most electronegative of the atoms.

C) Hydrogen fluoride can participate in hydrogen bonding.

D) HF is very reactive and can react and dissolve glass.

E) HF is a weak acid, and doesn't completely dissociate.

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

170) Identify the following compound(s) having the greatest London dispersion forces between like molecules?

An illustration shows the structure of four compounds. The first compound labeled 1 has a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms. C 2 and C 3 are each bonded to two hydrogen atoms. C 4 is bonded to a hydrogen atom and another carbon atom which is further bonded to three hydrogen atoms. The second compound labeled 2 has a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, and C 2, C 3, and C 4 are each bonded to two hydrogen atoms, respectively. The third compound labeled 3 has a central carbon atom which is bonded to four carbon atoms, each further bonded to three hydrogen atoms, respectively. The fourth compound labeled 4 has a six-carbon chain in which C 1 and C 6 are each bonded to three hydrogen atoms, and C 2, C 3, C 4, and C 5 are each bonded to two hydrogen atoms.

A) I

B) II

C) III

D) IV

E) II and III

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

171) Identify the following compound(s) having the highest boiling point?

An illustration shows the structure of four compounds. The first compound labeled 1 shows a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, and C 2, C 3, and C 4 are each bonded to two hydrogen atoms, respectively. The second compound labeled 2 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 are each bonded to two hydrogen atoms, and C 4 is bonded to two hydrogen atoms and an oxygen atom which is further bonded to a hydrogen atom. The third compound labeled 3 has a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, C 2 and C 4 are each bonded to two hydrogen atoms, and C 3 is replaced by an oxygen atom. The fourth compound labeled 4 has a three-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 is bonded to two hydrogen atoms, and C 3 is bonded to two hydrogen atoms and a chlorine atom.

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

172) Identify the following compound(s) having the lowest boiling point?

An illustration shows the structure of four compounds. The first compound labeled 1 shows a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, and C 2, C 3, and C 4 are each bonded to two hydrogen atoms, respectively. The second compound labeled 2 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 are each bonded to two hydrogen atoms, and C 4 is bonded to two hydrogen atoms and an oxygen atom which is further bonded to a hydrogen atom. The third compound labeled 3 has a four-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, C 2 is bonded to two hydrogen atoms, and C 3 is bonded to a hydrogen atom and another carbon atom which is further bonded to three hydrogen atoms. The fourth compound labeled 4 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 are each bonded to two hydrogen atoms, and C 4 is bonded to two hydrogen atoms and a chlorine atom.

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

173) Which of the following compounds have the lowest boiling point?

A) CH3Cl

B) CH2Cl2

C) CH4

D) CHCl3

E) CCl4

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

174) Identify the following compound(s) having the lowest boiling point?

An illustration shows the structure of four compounds. The first compound labeled 1 has a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms. C 2 and C 3 are each bonded to two hydrogen atoms. C 4 is bonded to a hydrogen atom and another carbon atom which is further bonded to three hydrogen atoms. The second compound labeled 2 has a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, and C 2, C 3, and C 4 are each bonded to two hydrogen atoms, respectively. The third compound labeled 3 has a central carbon atom which is bonded to four carbon atoms, each further bonded to three hydrogen atoms, respectively. The fourth compound labeled 4 has a six-carbon chain in which C 1 and C 6 are each bonded to three hydrogen atoms, and C 2, C 3, C 4, and C 5 are each bonded to two hydrogen atoms.

A) I

B) II

C) III

D) IV

E) I and IV

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

175) Rank the following compounds in order of decreasing boiling point.

An illustration shows the structure of four compounds. The first compound labeled 1 has a four-carbon chain in which C 1 and C 4 are each bonded to three hydrogen atoms. C 2 is bonded to two hydrogen atoms. C 3 is bonded to a hydrogen atom and another carbon atom which is further bonded to three hydrogen atoms. The second compound labeled 2 has a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, and C 2, C 3, and C 4 are each bonded to two hydrogen atoms, respectively. The third compound labeled 3 has a central carbon atom which is bonded to four carbon atoms, each further bonded to three hydrogen atoms, respectively. The fourth compound labeled 4 has a six-carbon chain in which C 1 and C 6 are each bonded to three hydrogen atoms, and C 2, C 3, C 4, and C 5 are each bonded to two hydrogen atoms.

A) III > I > IV > II

B) II > I > IV > III

C) III > I > II > IV

D) IV > II > I > III

E) I > III > II > IV

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

176) Rank the following compounds in order of decreasing boiling point.

An illustration shows the structure of four compounds. The first compound labeled 1 shows a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, and C 2, C 3, and C 4 are each bonded to two hydrogen atoms, respectively. The second compound labeled 2 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 are each bonded to two hydrogen atoms, and C 4 is bonded to two hydrogen atoms and an oxygen atom which is further bonded to a hydrogen atom. The third compound labeled 3 has a four-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, C 2 is bonded to two hydrogen atoms, and C 3 is bonded to a hydrogen atom and another carbon atom which is further bonded to three hydrogen atoms. The fourth compound labeled 4 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 are each bonded to two hydrogen atoms, and C 4 is bonded to two hydrogen atoms and a nitrogen atom which is further bonded to two hydrogen atoms.

A) III > I > IV > II

B) II > IV > I > III

C) III > I > II > IV

D) IV > II > I > III

E) I > III > II > IV

Diff: 3

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

177) Rank the following compounds in order of decreasing boiling point.

An illustration shows structure of four compounds. The first compound labeled 1 shows a four-carbon chain, in which C 1 is bonded to a methyl group. C 2, C 3, and C 4 are each bonded to two hydrogen atoms. C 4 is further bonded to an O H group. The second compound labeled 2 shows a central oxygen atom. The oxygen atom is bonded to two carbon atoms on each side, in which one carbon atom is bonded to two hydrogen atoms and another carbon atom is bonded to three hydrogen atoms. The third compound labeled 3 shows a three-carbon chain, in which C 1, C 2, and C 3 are each bonded to two hydrogen atoms. C 1 and C 3 are each further bonded to an O H group. The fourth compound labeled 4 has a four-carbon chain. C 1 and C 4 are each bonded to three hydrogen atoms. C 2 is bonded to two hydrogen atoms. C 3 is bonded to a hydrogen atom at the bottom and an O bonded to an H atom at the top.

A) III > I > IV > II

B) II > IV > III > I

C) III > I > II > IV

D) IV > II > I > III

E) I > III > II > IV

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

178) For the following equation, how many hydrogen atoms are added or lost?

An illustration shows a reaction. The reactant that has a SMILES string of CC1(CCCCC1)C=C yields a product that has a SMILES string of CC1=C(CCCCC1)C.

A) one hydrogen atom added

B) two hydrogen atoms added

C) one hydrogen atom lost

D) two hydrogen atoms lost

E) no change in the number of hydrogen atoms

Diff: 2

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

179) Identify the following compound(s) expected to be the most soluble in water?

An illustration shows the structure of four compounds. The first compound labeled 1 shows a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, and C 2, C 3, and C 4 are each bonded to two hydrogen atoms, respectively. The second compound labeled 2 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 are each bonded to two hydrogen atoms, and C 4 is bonded to two hydrogen atoms and an oxygen atom which is further bonded to a hydrogen atom. The third compound labeled 3 has a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, C 2 and C 4 are each bonded to two hydrogen atoms, and C 3 is replaced by an oxygen atom. The fourth compound labeled 4 has a three-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 is bonded to two hydrogen atoms, and C 3 is bonded to two hydrogen atoms and a chlorine atom.

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 1

Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility

180) Identify the following compound(s) expected to be the most soluble in butane, CH3CH2CH2CH3?

An illustration shows the structure of four compounds. The first compound labeled 1 shows a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, and C 2, C 3, and C 4 are each bonded to two hydrogen atoms, respectively. The second compound labeled 2 has a four-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 and C 3 are each bonded to two hydrogen atoms, and C 4 is bonded to two hydrogen atoms and an oxygen atom which is further bonded to a hydrogen atom. The third compound labeled 3 has a five-carbon chain in which C 1 and C 5 are each bonded to three hydrogen atoms, C 2 and C 4 are each bonded to two hydrogen atoms, and C 3 is replaced by an oxygen atom. The fourth compound labeled 4 has a three-carbon chain in which C 1 is bonded to three hydrogen atoms, C 2 is bonded to two hydrogen atoms, and C 3 is bonded to two hydrogen atoms and a chlorine atom.

A) I

B) II

C) III

D) IV

E) II and III

Diff: 2

Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility

181) For soap molecules to remove and dissolve oil in water, what molecular features are needed?

A) one end of the molecule must be polar

B) the compound must contain oxygen atoms

C) one end of the molecule must be nonpolar

D) Both A and C

E) All A, B and C

Diff: 2

Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility

182) Amino acids are the building blocks of proteins. Which statement best describes the physical properties of the following amino acid?

An illustration shows the structure of a compound. It has a nitrogen atom carrying a lone pair of electrons bonded to two hydrogen atoms and a carbon atom which is further bonded to two hydrogen atoms and another carbon atom which is double bonded to an oxygen atom carrying two lone pairs of electrons and single bonded to another oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom.

A) high melting point and low solubility in water

B) large dipole moment and no hydrogen bonding

C) high melting point and large dipole moment

D) low solubility in water and small dipole moment

E) small dipole moment and hydrophobic

Diff: 2

Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility

183) Which statement best describes the physical properties of the following sugar?

An illustration shows the structure of a compound. It has a cyclohexane ring in which C 1 is replaced by an oxygen atom. C 2, C 3, C 4, and C 5 are each bonded to a hydroxyl group and a hydrogen atom, respectively. C 6 is bonded to a hydrogen atom and another carbon atom which is further bonded to two hydrogen atoms and a hydroxyl group, respectively.

A) high melting point and high solubility in water

B) large dipole moment and no hydrogen bonding

C) low melting point and large dipole moment

D) low solubility in water and large dipole moment

E) small dipole moment and hydrophobic

Diff: 2

Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility

184) Naproxen, sold under the trade name Aleve, has the following structure. What is the molecular formula for naproxen?

An illustration shows a compound that has a SMILES string of CC(c1ccc2cc(ccc2c1)OC)C(=O)O.

A) C13H15O3

B) C14H14O3

C) C12H16O3

D) C14H16O3

E) C14H18O3

Diff: 2

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

185) AZT, used in the treatment of AIDS, has the following structure. What is the molecular formula for AZT?

An illustration shows a compound. It has a cyclohexane ring in which C 1 is bonded to a methyl group, C 2 and C 4 are each double bonded to an oxygen atom, C 3 is replaced by an N H group, C 1 and C 6 are double bonded to each other, and C 5 is replaced by a nitrogen atom which is further bonded to a C 2 of a cyclopentane ring in which C 1 is replaced by an oxygen atom, C 4 is bonded to an N 3 group and C 5 is bonded to a methylene group which is further bonded to a hydroxyl group.

A) C9H14N5O4

B) C9H9N5O4

C) C9H12N5O4

D) C10H13N5O4

E) C11H12N5O4

Diff: 2

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

186) Capsaicin, found in peppers, has the following structure. What is the molecular formula for capsaicin?

An illustration shows a compound that has a SMILES string of CC(C)C=CCCCCC(=O)NCc1ccc(c(c1)OC)O.

A) C18H27NO3

B) C17H25NO3

C) C18H30NO3

D) C19H27NO3

E) C18H24NO3

Diff: 2

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa

187) Of the following examples, which would be considered organic compounds?

An illustration shows four compounds. The first compound is N a C l. The second compound is C H 3 B r. The third structure is H 2 O. The fourth structure is C H 3 O C H 3.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 1

Learning Objective: 1.1 Compare and contrast organic and inorganic compounds

188) Constitutional isomers differ in ________.

A) physical properties

B) atomic connectivity

C) molecular formula

D) A and B

E) B and C

Diff: 1

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

189) What is the relationship between the following compounds?

An illustration shows the structure of two compounds. The first compound has a SMILES string of 
CC(=O)CC=C. The second compound has SMILES string of CC(=C)C(=O)C.

A) isotopes

B) constitutional isomers

C) the same structure

D) composed of different elements

E) no relationship

Diff: 1

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

190) What is the relationship between the following compounds?

An illustration shows the structure of two compounds. The first compound has a SMILES string of 
CCOC. The second compound has a SMILES string of CCCO.

A) resonance isomers

B) constitutional isomers

C) empirical isomers

D) isotopes

E) There is no relationship

Diff: 1

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

191) Which of the following compounds are constitutional isomers?

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of Cc1ccc(c(c1Cl)Br)C. The second compound labeled 2 has a SMLES string of CC(c1ccccc1Cl)Br. The third compound labeled 3 has a SMILES string of Cc1ccc(c(c1Br)C)Cl. The fourth compound labeled 4 has a benzene ring in which C 1 is bonded to a bromine atom, C 2 is bonded to a chlorine atom, C 3 is bonded to a methyl group, and C 5 is bonded to a two-carbon chain.

A) I and II

B) I and III

C) I, II and IV

D) II, III and IV

E) I, II, and III

Diff: 2

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

192) Which of the following compounds are constitutional isomers of each other?

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of C(C(Cl)Cl)Cl. The second compound labeled 2 has a SMILES string of C(C(Cl)Cl)(Cl)Cl. The third compound labeled 3 has a SMILES string of C(CCl)Cl. The fourth compound labeled 4 has a SMILES string of CC(Cl)(Cl)Cl.

A) I and II

B) II and III

C) III and IV

D) I and IV

E) II and IV

Diff: 2

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

193) Identify three constitutional isomers having the molecular formula C4H8BrCl.

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCC(CCl)Br. The second compound labeled 2 has a SMILES string of CC(C(C)Br)Br. The third compound labeled 3 has a SMILES string of CCC(C)(Cl)Br. The fourth compound labeled 4 has a four-carbon chain in which C 3 is bonded to a bromine atom and a chlorine atom, and C 4 is bonded to a chlorine atom. The fifth compound labeled 5 has a SMILES string of CC(C(C)Br)Cl.

A) I, II, and III

B) II, III, and IV

C) III, IV, and IV

D) I, III, and V

E) II, III, and V

Diff: 1

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

194) Identify three constitutional isomers having the molecular formula C4H8O.

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of C#CCCO. The second compound labeled 2 has a SMILES string of C=CCCO. The third compound labeled 3 has a SMILES string of CCCC=O. The fourth compound labeled 4 has a SMILES string of 
COCC=C. The fifth compound labeled 5 has a SMILES string of CCCCO.

A) I, II, and III

B) II, III, and IV

C) III, IV, and IV

D) I, II, and IV

E) II, III, and V

Diff: 2

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

195) Which of the following represent identical molecules?

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CC(C(CCl)Br)Br. The second compound labeled 2 has a SMILES string of CC(C(CBr)Cl)Br. The third compound labeled 3 has a SMILES string of CC(C(C)(Cl)Br)Cl. The fourth compound labeled 4 has a SMILES string of CC(C(CBr)Cl)Br. The fifth compound labeled 5 has a SMILES string of CC(C(CBr)Br)Cl.

A) I and II

B) II and III

C) III and IV

D) IV and V

E) II and IV

Diff: 2

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

196) What are the formal charges on the atoms indicated for the following structure?

An illustration shows the structure of a compound. It has a central sulfur atom which is bonded to two oxygen atoms each carrying three lone pairs of electrons and two oxygen atoms each carrying two lone pairs of electrons which is each further bonded to a hydrogen atom. An arrow labeled 1, points toward the one of the oxygen atoms carrying two lone pairs of electrons. An arrow labeled 2 points toward the oxygen atom carrying three lone pairs of electrons. An arrow labeled 3 points toward the sulfur atom.

A) I = 0; II = 1+; III = 2+

B) I = 1-; II = 0; III = 1+

C) I = 1+; II = 1-; III = 2+

D) I = 1-; II = 1+; III = 1-

E) I = 0; II = 1-; III = 2+

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

197) What are the formal charges on fluorine and nitrogen in the following structure?

An illustration shows the structure of a compound. It has a boron atom bonded to three fluorine atoms each carrying three lone pairs of electrons and a nitrogen atom which is further bonded to three hydrogen atoms.

A) F = 1+, N = 1+

B) F = 0, N = 1-

C) F = 1-, N = 1-

D) F = 0, N = 1+

E) F = 1+, N = 1-

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

198) Which of the following have a 1+ formal charge on the central atom?

An illustration shows the structure of five compounds. The first compound labeled 1 has a beryllium atom bonded to two hydrogen atoms. The second compound labeled 2 has a central boron atom bonded to four hydrogen atoms. The third compound labeled 3 has a central nitrogen atom carrying a lone pair of electrons bonded to three hydrogen atoms. The fourth compound labeled 4 has a central nitrogen atom which is bonded to four hydrogen atoms. The fifth compound labeled 5 has an oxygen atom carrying a lone pair of electrons bonded to three hydrogen atoms.

A) I

B) II

C) III

D) III and V

E) IV and V

Diff: 2

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

199) Which of the following principle states "The lowest energy orbital is filled first"?

A) Aufbau principle

B) Pauli exclusion principle

C) Hund's Rule

D) Heizenberg Uncertainty principle

E) Le Chatelier's principle

Diff: 1

Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons

200) Which of the indicated carbon atoms in the following compound are sp2 hybridized?

An illustration shows the structure of a compound. It has a five-carbon chain in which C 2 is double bonded to an oxygen atom, and C 4 and C 5 are double bonded to each other. An arrow labeled 1, points toward C 5. An arrow labeled 2 points toward C 3. An arrow labeled 3 points toward C 2. An arrow labeled 4 points at C 1.

A) I and II

B) III and IV

C) II and III

D) I and III

E) II and IV

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

201) What is the hybridization for each of the indicated carbon atoms in the following compound?

An illustration shows the structure of a compound that has a SMILES string of CC=CCCC#C. An arrow labeled 1, points toward C 2. An arrow labeled 2 points toward C 5. An arrow labeled 3 points toward C 7.

A) I = sp3, II = sp2, III = sp

B) I = sp2, II = sp, III = sp2

C) I = sp, II = sp2, III = sp3

D) I = sp, II = sp2, III = sp

E) I = sp2, II = sp3, III = sp2

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

202) How many ssp2 sigma bonds are in the following compound?

An illustration shows a compound that has a SMILES string of C/C=C/C=C.

A) 2

B) 3

C) 4

D) 5

E) 6

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

203) The C2–C3 bond in the following compound results from the overlap of which orbitals?

An illustration shows a compound that has a SMILES string of CC(=O)CC=C, in which the carbon atoms 2 and 3 are labeled.

A) spsp2

B) spsp3

C) sp2—sp2

D) sp2—sp3

E) sp3—sp2

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

204) The sigma bond that is part of C=C in the following compound results from the overlap of which orbitals?

An illustration shows a compound that has a SMILES string of CC(=O)CC=C.

A) spsp2

B) spsp3

C) sp2—sp2

D) sp2—sp3

E) sp3—sp2

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

205) How many pi bonds are present in the following compound?

An illustration shows a compound that has a SMILES string of CC(=O)CC=C.

A) one

B) two

C) three

D) four

E) five

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

206) How many pi bonds are present in the following compound?

An illustration shows the structure of a compound. It has a benzene ring in which C 1 is bonded to a seven-carbon chain in which C 2 is double bonded to C 3, and C 6 is triple bonded to C 7.

A) two

B) three

C) four

D) five

E) six

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

207) How many sigma bonds are present in the following compound?

An illustration shows the structure of a compound. It has a benzene ring in which C 1 is bonded to a seven-carbon chain in which C 2 is double bonded to C 3, and C 6 is triple bonded to C 7.

A) 20

B) 22

C) 24

D) 25

E) 27

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

208) The sigma bond that is part of C=N in the following compound results from the overlap of which orbitals?

An illustration shows a compound that has a SMILES string of C/C=N/O.

A) sp2sp2

B) spsp

C) sp2—sp3

D) sp3—sp3

E) sp3—sp2

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

209) The bonds indicated by the arrow in the following compound results from the overlap of which orbitals?

An illustration shows a compound that has a SMILES string of CC#CC=C. An arrow points toward the double bond.

A) sp2sp2

B) sp3—sp3

C) pp

D) Both A and B

E) Both A and C

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

210) Which orbitals are involved in the C–O sigma bond in acetone, shown below?

An illustration shows a compound that has a SMILES string of CC(=O)C.

A) Csp2–Osp2

B) Csp3–Osp3

C) Csp–Osp

D) Cp–Op

E) Csp–Op

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

211) Which of the following best describes the orbitals involved in the formation of the C=O bond in acetone, shown below?

An illustration shows a compound that has a SMILES string of CC(=O)C.

A) σ = Csp2 - Osp2 and π = Csp2 - Osp2

B) σ = Csp2 - Osp2 and π = Cp - Op

C) σ = Csp3 - Osp2 and π = Cp - Op

D) σ = Cp - Op and π = Csp2 - Osp2

E) σ = Csp - Osp and π = Cp - Op

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

212) Identify the shortest bond in the following compound.

An illustration shows a compound that has a SMILES string of CC#CC=C. An arrow labeled 1, points toward the double bond. An arrow labeled 1, points toward the double bond. An arrow labeled 2 points at toward the bond between C 2 and C 3. An arrow labeled 3 points toward the triple bond. An arrow labeled 4 points toward the bond between C 4 and C 5.

A) I

B) II

C) III

D) IV

E) I and III are of equal length

Diff: 1

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

213) Identify the longest C–C bond(s) in the following compound?

An illustration shows a compound that has a SMILES string of CC#CC=C. An arrow labeled 1, points toward the double bond. An arrow labeled 1, points toward the double bond. An arrow labeled 2 points at toward the bond between C 2 and C 3. An arrow labeled 3 points toward the triple bond. An arrow labeled 4 points toward the bond between C 4 and C 5.

A) I

B) II

C) III

D) IV

E) II and IV are of equal length

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

214) Identify the longest C–C bond(s) in the following compound?

An illustration shows the structure of a compound. It has a seven-carbon chain in which C 1, C 5, and C 6 are each bonded to two hydrogen atoms. C 2 is bonded to a hydrogen atom. C 1 is double bonded to C 2. C 3 is triple bonded to C 4. C 7 is bonded to three hydrogen atoms. An arrow labeled 1, points toward the double bond. An arrow labeled 2 points toward the bond between C 2 and C 3. An arrow labeled 3 points toward the triple bond. An arrow labeled 4 points toward the bond between C 4 and C 5. An arrow labeled 5 points toward the bond between C 6 and C 7.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

215) Identify the longest C–C bond(s) in the following compound?

An illustration shows a compound that has a SMILES string of CCCC#CC=C. An arrow labeled 1, points toward the double bond. An arrow labeled 2 points toward the bond between C 2 and C 3. An arrow labeled 3 points toward the triple bond. An arrow labeled 4 points toward the bond between C 4 and C 5. An arrow labeled 5 points toward the bond between C 6 and C 7.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

216) Rank the indicated C–C bonds in increasing order of bond length.

An illustration shows a compound that has a SMILES string of CC#CC=C. An arrow labeled 1, points toward the double bond. An arrow labeled 1, points toward the double bond. An arrow labeled 2 points at toward the bond between C 2 and C 3. An arrow labeled 3 points toward the triple bond. An arrow labeled 4 points toward the bond between C 4 and C 5.

A) I < II < III < IV

B) II < IV < III < I

C) III < I < IV < II

D) III < I < II < IV

E) IV < II < I < III

Diff: 3

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

217) Following is the structure for Propranolol, an antihypertensive drug. Identify the hybridization state, molecular geometry and approximate bond angle at the indicated oxygen atom in Propranolol.

An illustration shows the structure of a compound. It has two benzene rings fused together. All the carbon atoms except C 3 of the second benzene ring are each bonded to a hydrogen atom. C 3 of the second benzene ring is further bonded to a six-carbon chain in which C 1 is replaced by an oxygen atom carrying two lone pairs of electrons (an arrow points toward this oxygen atom). C 2 and C 4 are each bonded to two hydrogen atoms. C 2 is bonded to a hydrogen atom and an oxygen atom carrying two lone pairs of electrons which is further bonded to a hydrogen atom. C 5 is replaced by a nitrogen atom carrying a lone pair of electrons and is further bonded to a hydrogen atom. C 6 is bonded to a hydrogen atom and two methyl groups.

A) sp2, tetrahedral, 109°

B) sp2, bent, 120°

C) sp3, tetrahedral, 109.5°

D) sp3, bent, ~109.5°

E) sp2, bent, 180°

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

218) Following is the structure for Propranolol, an antihypertensive drug. Identify the hybridization state, molecular geometry and approximate bond angle at the nitrogen atom in Propranolol.

An illustration shows a compound that has a SMILES string of CC(C)NCC(COc1ccc2ccccc2c1)O.

A) sp2, tetrahedral, 109°

B) sp2, trigonal planar, 120°

C) sp3, tetrahedral, ~109.5°

D) sp3, trigonal pyramidal, ~109.5°

E) sp2, trigonal pyramidal, 180°

Diff: 2

Learning Objective: 1.11 Describe VSEPR theory

219) Rank the following compounds in order of decreasing dipole moment.

An illustration shows the structures of three compounds. The first compound labeled 1 has a SMILES string of C1CC(=O)CC(=O)C1. The second compound labeled 2 has a SMILES string of C1CC(=O)CCC1=O. The third compound labeled 3 has a SMILES string of C1CCC(=O)C(=O)C1.

A) I > II > III

B) II >III > I

C) I > III > II

D) III > I > II

E) II > I > III

Diff: 2

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond

220) What is the strongest intermolecular force possible between molecules of the following structure?

An illustration shows a compound that has a SMILES string of CCCCO.

A) ion-dipole interactions

B) London dispersion forces

C) dipole-dipole interactions

D) hydrogen bonding

E) covalent bonding

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

221) What is the strongest intermolecular force possible between molecules of the following structure?

An illustration shows a compound that has a SMILES string of CCCCS.

A) ion-dipole interactions

B) London dispersion forces

C) dipole-dipole interactions

D) hydrogen bonding

E) covalent bonding

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

222) Which of the following compounds has the greatest London dispersion forces between like molecules?

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCC(C)C. The second compound labeled 2 has a SMILES string of CCCCC. The third compound labeled 3 has a SMILES string of CC(C)(C)C. The fourth compound labeled 4 has a SMILES string of CCCCCC. The fifth compound labeled 5 has a SMILES string of CC(C)C(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

223) Which of the following compounds is expected to have the highest boiling point?

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCCC. The second compound labeled 2 has a SMILES string of CCCCO. The third compound labeled 3 has a SMILES string of CCOCC. The fourth compound labeled 4 has a SMILES string of CCCOC. The fifth compound labeled 5 has a SMILES string of CCCCCl.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

224) Which of the following compounds is expected to have the lowest boiling point?

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCCC. The second compound labeled 2 has a SMILES string of CCCCO. The third compound labeled 3 has a SMILES string of CCOCC. The fourth compound labeled 4 has a SMILES string of CCCOC. The fifth compound labeled 5 has a SMILES string of CCCCCl.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

225) Identify the following compound expected to have the lowest boiling point?

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCC(C)C. The second compound labeled 2 has a SMILES string of CCCCC. The third compound labeled 3 has a SMILES string of CC(C)(C)C. The fourth compound labeled 4 has a SMILES string of CCCCCC. The fifth compound labeled 5 has a SMILES string of CC(C)C(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

226) Rank the following compounds in decreasing order of boiling point.

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of CCCC(C)C. The second compound labeled 2 has a SMILES string of CCCCC. The third compound labeled 3 has a SMILES string of CC(C)(C)C. The fourth compound labeled 4 has a SMILES string of CCCCCC.

A) III > I > IV > II

B) II > I > IV > III

C) III > I > II > IV

D) IV > II > I > III

E) I > III > II > IV

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

227) Rank the following compounds in decreasing order of boiling point.

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of CCCCC. The second compound labeled 2 has a SMILES string of CCCCO. The third compound labeled 3 has a SMILES string of CCCC(C)C. The fourth compound labeled 4 has a SMILES string of CCCCN.

A) III > I > IV > II

B) II > IV > I > III

C) III > I > II > IV

D) IV > II > I > III

E) I > III > II > IV

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

228) Rank the following compounds in decreasing order of boiling point.

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of CCCCO. The second compound labeled 2 has a SMILES string of CCOCC. The third compound labeled 3 has a SMILES string of C(CO)CO. The fourth compound labeled 4 has a SMILES string of CCC(C)O.

A) III > I > IV > II

B) II > IV > III > I

C) III > IV > I > II

D) IV > II > I > III

E) I > III > II > IV

Diff: 2

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

229) Identify the following compound expected to be the most soluble in water?

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCCC. The second compound labeled 2 has a SMILES string of CCCCO. The third compound labeled 3 has a SMILES string of CCOCC. The fourth compound labeled 4 has a SMILES string of CCCOC. The fifth compound labeled 5 has a SMILES string of CCCCCl.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility

230) Identify the following compound expected to be the most soluble in butane, CH3CH2CH2CH3?

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCCC. The second compound labeled 2 has a SMILES string of CCCCO. The third compound labeled 3 has a SMILES string of CCOCC. The fourth compound labeled 4 has a SMILES string of CCCOC. The fifth compound labeled 5 has a SMILES string of CCCCCl.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility

231) Amino acids are the building blocks of proteins. Which statement best describes the physical properties of the following amino acid?

An illustration shows a compound that has a SMILES string of C(C(=O)O)N.

A) high melting point and low solubility in water

B) large dipole moment and no hydrogen bonding

C) high melting point and large dipole moment

D) low solubility in water and small dipole moment

E) small dipole moment and hydrophobic

Diff: 2

Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility

232) Which statement best describes the physical properties of the following sugar?

An illustration shows a compound that has a SMILES string of C(C1C(C(C(C(O1)O)O)O)O)O.

A) high melting point and high solubility in water

B) large dipole moment and no hydrogen bonding

C) low melting point and large dipole moment

D) low solubility in water and large dipole moment

E) small dipole moment and hydrophobic

Diff: 2

Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility

© (2021) John Wiley & Sons, Inc. All rights reserved. Instructors who are authorized users of this course are permitted to download these materials and use them in connection with the course. Except as permitted herein or by law, no part of these materials should be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise.

Document Information

Document Type:
DOCX
Chapter Number:
1
Created Date:
Aug 21, 2025
Chapter Name:
Chapter 1 Gen Chemistry – Bonds, Properties
Author:
David R. Klein

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