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Ch4 Test Bank Docx Alkanes And Cycloalkanes

Organic Chemistry, 4e (Klein)

Chapter 4 Alkanes and Cycloalkanes

1) What is the parent chain of the following compound?

An illustration depicts a compound with a SMILES string of CCC(C)CCC(C)CC.

A) octane

B) hexane

C) heptane

D) decane

E) nonane

Diff: 1

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

2) What is the parent chain of the following compound?

An illustration depicts a compound that has an eight-carbon chain. C 3 is bonded to a methyl group. C 4 is bonded to an ethyl group. C 5 is bonded to a butyl group. C 6 is bonded to a methyl group.

A) hexane

B) heptane

C) octane

D) nonane

E) decane

Diff: 1

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

3) What is the parent chain of the following compound?

An illustration depicts a compound which has a linear carbon chain of six carbon atoms. From right to left, A single bond branches off from C 2 and is connected with another carbon atom which is further connected to a methyl group. Another single bond branches off from C 4 and is connected with another carbon atom. This carbon atom is bonded to two other methyl groups.

A) pentane

B) hexane

C) heptane

D) octane

E) nonane

Diff: 1

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

4) What is the parent chain of the following compound?

A) pentane

B) hexane

C) heptane

D) octane

E) nonane

Diff: 1

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

5) What is the IUPAC name of the following compound?

An illustration depicts a compound which has a linear carbon chain of seven carbon atoms. From right to left, A single bond branches off from C 3 and is connected with another carbon atom which is further connected to a methyl group. Another single bond branches off from C 5 and is connected with another carbon atom. This carbon atom is bonded to two other methyl groups.

A) 3-isopropyl-5-ethylheptane

B) 2-methyl-3-ethyl-5-ethylheptane

C) 3-ethyl-5-isopropylheptane

D) 2-methyl-3,5-diethylheptane

E) 3,5-diethyl-2-methylheptane

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

6) What is the IUPAC name of the following compound?

An illustration depicts a compound with a SMILES string of CCC(C)CCC(C)CC.

A) 2,5-diethylhexane

B) 3,6-dimethyloctane

C) 2-ethyl-5-methylheptane

D) 2,5-dimethylheptane

E) 1,2-di-sec-butylethane

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

7) What is the IUPAC name of the following compound?

An illustration depicts a compound which has a linear carbon chain of six carbon atoms. From right to left, C 2, C 3, and C 5 are each bonded to an ethyl group.

A) 2,3,5-triethylhexane

B) 2,4,5-triethylhexane

C) 2,4-diethyl-5-methylheptane

D) 4-ethyl-3,6-dimethyloctane

E) 3,6-dimethyl-5-ethyloctane

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

8) What is the IUPAC name of the following compound?

An illustration depicts a compound with a SMILES string of CCC1CCCCC1C.

A) 1-ethyl-2-methylcyclohexane

B) 2-ethyl-1-methylcyclohexane

C) 1-ethyl-2-methylhexane

D) cyclononane

E) ethylmethylcyclohexane

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

9) What is the IUPAC name of the following compound?

An illustration depicts a compound with a SMILES string of CCC1CCC(C1C)C.

A) 2,3-dimethyl-1-ethyl-cyclopropane

B) 1-ethyl-2,3-dimethylcyclopentane

C) 3-ethyl-1,2-dimethyl-cyclopentane

D) 1-ethyl-2,3-methylcyclohexane

E) 1,2,3-ethyl-dimethylcyclopentane

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

10) What is the IUPAC name of the following compound?

An illustration depicts a compound with two cyclopentane rings fused together. The C 2 and C 4 atoms are each bonded to a methyl group.

A) 3,6-dimethylbicyclo[3.3.1]octane

B) 2,5-dimethylbicyclo[3.3.0]octane

C) 2,7-dimethylbicyclo[3.3.0]octane

D) 1,4-dimethylbicyclo[3.3.1]octane

E) 3,8-dimethylbicyclo[3.3.0]octane

Diff: 3

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

11) What is the IUPAC name of the following compound?

An illustration depicts a compound with a SMILES string of CCC(CC)C(C)C.

A) 3-isopropylpentane

B) 3-ethyl-4-methylpentane

C) 1,1-diethyl-2-methylpropane

D) 3-(1,1-dimethylmethyl)pentane

E) 3-ethyl-2-methylpentane

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

12) What is the IUPAC name of the following compound?

A) 4-butyl-5-ethyl-3,6-dimethylheptane

B) 3-sec-butyl-4-butyl-5-methylheptane

C) 3-butyl-2,4,5-triethyl-hexane

D) 5-sec-butyl-4-ethyl-3-methylnonane

E) 3,4-di-sec-butyl-octane

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

13) What is the IUPAC name of the following compound?

An illustration depicts a compound which has a SMILES string of CC1CCC(C1)(C)C.

A) 1,1,3-trimethylcyclopentane

B) 1,3,3-trimethylcyclopentane

C) 1,1,3-trimethylcyclopropane

D) 1,3,3-trimethylcyclopropane

E) 1-methyl-3-isopropylcyclopentane

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

14) What is the IUPAC name of the following compound?

An illustration depicts a compound with a ring of eight carbon atoms. The C 1 atom is bonded to another carbon atom which is further bonded to three methyl groups. The C 3 atom is bonded to a methyl group.

A) 1-methyl-3-tert-butylcyclooctane

B) 1-tert-butyl-3-methylcyclooctane

C) 1-methyl-7-tert-butylcyclooctane

D) 1-tert-butyl-7-methylcyclooctane

E) 3-methyl-1-(dimethylethyl)cyclooctane

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

15) Which of the following have an isopropyl group as a substituent on the parent chain?

An illustration depicts three compounds. The compound one has a linear carbon chain of six carbon atoms. The C 3 is bonded to another carbon atom which is further bonded to two methyl groups. The compound two has a linear carbon chain of seven carbon atoms. The C 4 is bonded to another carbon atom which is further bonded to two methyl groups. The compound three has a SMILES string of CC(C)C1CCCC1.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 1

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

16) What is the common name of the following substituent?

An illustration depicts a compound, labeled parent with a SMILES string of CCC(C)C.

A) isopropyl

B) tert-butyl

C) isobutyl

D) sec-butyl

E) neopentyl

Diff: 1

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

17) Which of the following is [2.2.2]bicyclooctane?

An illustration depicts five compounds. The first compound has a SMILES string of C1CC2CCC1CC2. The second compound has a SMILES string of C1CC2CCC1C2. The third compound has a SMILES string of C1CC2CC1C2. The fourth compound has a SMILES string of C1CC2CCCC2C1. The fifth compound is a ten carbon alkane, in which C 1 is linked to C 4 through two methylene groups.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

18) Which of the following is a tert-butyl group?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

19) Which of the following is 3-ethyl-2,4,6-trimethyloctane?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

20) Which of the following is 3-ethyl-3-methylpentane?

An illustration depicts five compounds. The first compound has a SMILES string of CCC(C)C(C)C. The second compound has a SMILES string of CCC(CC)C(C)C. The third compound has a SMILES string of CCC(CC)(CC)CC. The fourth compound has a SMILES string of
CCC(C)(CC)CC. The fifth compound has a SMILES string of CCCC(C)(CC)CC.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

21) Which of the following is 1-cyclopropyl-3-methylcyclopentane?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

22) What is the IUPAC name of the following compound?

An illustration depicts a compound which has eleven carbon atoms, in which C 1 is connected to C 5 through the bridge of two methylene groups.

A) bicyclo[6.5.4]undecane

B) bicyclo[4.3.2]nonane

C) [4.3.2]bicyclononane

D) [2.3.4]bicycloundecane

E) bicyclo[4.3.2]undecane

Diff: 3

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

23) Which of the following IUPAC names represent structures that are constitutional isomers of C6H14?

$I U P A C names of five compounds are as follows: 1: hexane. 2: 2-methylhexane. 3: 2-methylpentane. 4: 2, 3-dimethylpentane. 5: 2, 3-dimethylbutane.$

A) I and II

B) III and V

C) I, III and V

D) II, III and IV

E) I, III and IV

Diff: 3

Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers

24) Which pair of the following compounds are constitutional isomers?

An illustration depicts four compounds. The first compound has a SMILES string of CC1CCC(C(C1)C)C. The second compound has a SMILES string of CC1CC(C(C1)C)C. The third compound has a SMILES string of
C1CCCCCCC1. The fourth compound has a SMILES string of CC1CC(C(CC1C)C)C.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 2

Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers

25) Which of the following compounds are constitutional isomers?

A) I and II

B) II and III

C) III and IV

D) I and IV

E) II and IV

Diff: 2

Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers

26) Which pair of the following compounds are constitutional isomers?

An illustration depicts four compounds. The first compound has a SMILES string of CCCC. The second compound has a SMILES string of C1CCC1 . The third compound has a SMILES string of CC(C)C. The fourth compound has a SMILES string of CCCCC.

A) I and III

B) II and IV

C) I and IV

D) II and III

E) I, II, and III

Diff: 2

Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers

27) What is the relationship between the following compounds?

An illustration depicts two compounds. The first compound has a SMILES string of CCC(C)CC. The second compound has a SMILES string of CCCC(C)C.

A) constitutional isomers

B) different representations of the same molecule

C) completely different/not constitutional isomers

D) isotopes

E) resonance hybrids

Diff: 1

Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers

28) What is the relationship between the following two compounds?

An illustration depicts two compounds. The first compound has a SMILES string of CCC(C)CC. The second compound has a SMILES string of CCCCC.

A) constitutional isomers

B) different representations of the same molecule

C) completely different/not constitutional isomers

D) isotopes

E) resonance hybrids

Diff: 1

Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers

29) What is the relationship between the following two compounds?

An illustration depicts two compounds. The first compound has a SMILES string of CCCCC. The second compound has a SMILES string of C1CCCC1.

A) constitutional isomers

B) different representations of the same molecule

C) completely different/not constitutional isomers

D) isotopes

E) resonance hybrids

Diff: 1

Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers

30) What is the relationship between the following two compounds?

An illustration depicts two compounds with each having a SMILES string of CCCCC. The second compound is linear.

A) constitutional isomers

B) different representations of the same molecule

C) completely different/not constitutional isomers

D) isotopes

E) resonance hybrids

Diff: 1

Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers

31) What is the relationship between the following two compounds?

An illustration depicts two compounds. The first compound has a SMILES string of CCCCC. The second compound has a SMILES string of CC(C)(C)C.

A) constitutional isomers

B) different representations of the same molecule

C) completely different/not constitutional isomers

D) isotopes

E) resonance hybrids

Diff: 1

Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers

32) What is the correct coefficient for oxygen that would balance the following combustion reaction?

An incomplete combustion reaction is as follows:
A compound with a SMILES string of CCC(C)C reacts with unknown moles (represented by a question mark) of O 2 to form 5 C O 2 and 6 H 2 O.

A) 2

B) 4

C) 6

D) 8

E) 10

Diff: 2

Learning Objective: 4.4 Define heat of combustion, describing how it can be measured

33) What is the correct coefficient for oxygen that would balance the following combustion reaction?

An incomplete combustion reaction is as follows:
2 moles of a compound with a SMILES string of CCCC(C)C reacts with unknown moles (represented by a question mark) of O 2 to form 12 C O 2 and 14 H 2 O.

A) 11

B) 13

C) 15

D) 17

E) 19

Diff: 2

Learning Objective: 4.4 Define heat of combustion, describing how it can be measured

34) Identify the correct coefficients required to balance the following combustion reaction?

An incomplete combustion reaction is as follows:
A compound that has a SMILES string of
C1CCCC1 with a Coefficient value of 2 reacts with O 2 to yield C O 2 and H 2 O. The blank spaces to the left of O 2, C O 2, and H 2 O are marked 1, 2 and 3 (in Roman Numerals), respectively.

A) I = 5; II = 10; III = 15

B) I = 15; II = 10; III = 10

C) I = 15; II = 10; III = 15

D) I = 10; II = 15; III = 10

E) I = 3; II = 2; III = 3

Diff: 3

Learning Objective: 4.4 Define heat of combustion, describing how it can be measured

35) Identify the correct coefficients required to balance the following combustion reaction?

An incomplete combustion reaction is as follows:
A compound that has a SMILES string of
CC(C)(C)C reacts with O 2 to yield C O 2 and H 2 O. The blank spaces to the left of O 2, C O 2, and H 2 O are marked 1, 2 and 3 (in Roman Numerals), respectively.

A) I = 4; II = 5; III = 12

B) I = 16; II = 10; III = 11

C) I = 8; II = 5; III = 6

D) I = 2; II = 4; III = 6

E) I = 9; II = 15; III = 5

Diff: 3

Learning Objective: 4.4 Define heat of combustion, describing how it can be measured

36) Identify the isomer of C9H20 that is the most stable?

A) nonane

B) 3-methyloctane

C) 2,2-dimethylheptane

D) 2,2,3,4-tetramethylpentane

E) 2,6-dimethylheptane

Diff: 2

Learning Objective: 4.4 Define heat of combustion, describing how it can be measured

37) The reaction shown below is an example of ________.

A chemical reaction is as follows:
The reactant that has a SMILES string of CCCCCCCCCCCC reacts with atmospheric H 2 at 450 degrees Celsius. The products have a SMILES string of CCCCC and CCCCCCC, respectively.

A) catalytic cracking

B) thermal cracking

C) catalytic reforming

D) thermal reforming

E) combustion

Diff: 2

Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons

38) The process that converts straight-chain alkanes into branched hydrocarbons is called ________.

A) hydrogenation

B) cracking

C) reforming

D) hydrolysis

E) combustion

Diff: 1

Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons

39) Identify the size of the hydrocarbon that is used in gasoline.

A) C1 — C4

B) C5 — C12

C) C12 — C18

D) C20 and higher nonvolatile liquids

E) C20 and higher nonvolatile solids

Diff: 1

Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons

40) Identify the size of the hydrocarbon that is used in natural gas.

A) C1 — C4

B) C5 — C12

C) C12 — C18

D) C20 and higher nonvolatile liquids

E) C20 and higher nonvolatile solids

Diff: 1

Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons

41) Identify the size of the hydrocarbon that is used in jet fuel.

A) C1 — C4

B) C5 — C12

C) C12 — C18

D) C20 and higher nonvolatile liquids

E) C20 and higher nonvolatile solids

Diff: 1

Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons

42) Identify the size of the hydrocarbon that is used in asphalt.

A) C1 — C4

B) C5 — C12

C) C12 — C18

D) C20 and higher nonvolatile liquids

E) C20 and higher nonvolatile solids

Diff: 1

Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons

43) Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

44) Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

45) Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

46) Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

47) Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

48) Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

An illustration depicts a compound with a SMILES string of CC[C@@H](C)[C@@H](C)CC. illustration of an eye is depicted. An upward sloping dashed arrow from the eye points toward the carbon atom that is wedged bonded to the methyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

49) Which of the following is the correct wedge and dash conformation for the following Newman projection?

An illustration depicting Newman projection of a compound is as follows:
The projection has inverted Y-shape at the front and sphere at the back. Front half: The substituents in clockwise direction reads, C H 3, H, and B r. Back half: The substituents in clockwise direction reads, B r, C H 3, and H.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

50) Which of the following is the correct wedge and dash conformation for the following Newman projection?

An illustration depicting Newman projection of a compound is as follows:
The projection has inverted Y-shape at the front and sphere at the back. Front half: The substituents bonded to a carbon atom in clockwise direction reads, E t, E t, and H. Back half: The substituents bonded to a carbon atom in clockwise direction reads, C H 3, H, and C H 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

51) Which of the following is the correct wedge and dash conformation for the following Newman projection?

An illustration depicting Newman projection of a compound is as follows:
The projection has inverted Y-shape at the front and sphere at the back. Front half: The substituents bonded to a carbon atom in clockwise direction reads, C H 3, H, and C H 3. Back half: The substituents bonded to a carbon atom in clockwise direction reads, H, E t, and H.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

52) Which of the following is the correct wedge and dash conformation for the following Newman projection?

An illustration depicting Newman projection of a compound is as follows:
The projection has inverted Y-shape at the front and sphere at the back. Front half: The substituents bonded to the front carbon atom in clockwise direction reads, C H 3, B r, and H. Back half: The substituents bonded to back carbon atom in clockwise direction reads, B r, C H 3, and H.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

53) Which of the following is the correct wedge and dash conformation for the following Newman projection?

An illustration depicting Newman projection of a compound is as follows:
The projection has inverted Y-shape at the front and sphere at the back. Front half: The substituents bonded to a carbon atom in clockwise direction reads, C H 3, H, and C H 3. Back half: The substituents bonded to a carbon atom in clockwise direction reads, C H 3, E t and H.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

54) Which of the following is the correct wedge and dash conformation for the following Newman projection?

An illustration depicting Newman projection of a compound is as follows:
The projection has inverted Y-shape at the front and sphere at the back. Front half: The substituents bonded to a carbon atom in clockwise direction reads, C H 3, C l, and C H 3. Back half: The substituents bonded to a carbon atom in clockwise direction reads, C H 3, E t and H.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes

55) Which of the following is a Newman projection of an eclipsed conformation for ethane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

56) Which of the following is a Newman projection of a staggered conformation for ethane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

57) Which of the following is a Newman projection of an eclipsed conformation for propane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

58) Which of the following is a Newman projection of a staggered conformation for propane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

59) Consider the energy diagram showing the conformational analysis of propane and match the indicated position with the correct conformation below.

An illustration depicts a graph that plots energy on the vertical axis versus dihedral angle on the horizontal axis. The values on the horizontal axis are ranged from 0 to 180. A wave with three crests and two troughs is plotted. The crest present in the middle is indicated using an arrow.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

60) What is the eclipsing cost of Br and H if the energy difference between the staggered and eclipsed conformations of bromoethane, shown in the box below, is 13 kJ/mol?

The compound has a SMILES string of CCBr.

A) 4 kJ/mol

B) 5 kJ/mol

C) 8 kJ/mol

D) 13 kJ/mol

E) 3.8 kJ/mol

Diff: 3

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

61) What is the energy difference between the staggered and eclipsed conformations of 2,2,-dimethylpropane?

A) 3.8 kJ/mol

B) 4 kJ/mol

C) 6 kJ/mol

D) 11 kJ/mol

E) 18 kJ/mol

Diff: 3

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

62) Which of the following is a gauche conformation for butane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

63) Which of the following is an anti conformation for butane?

A) I

B) II

C) III

D) IV

E) E

Diff: 1

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

64) Which of the following is a CH3—CH3 eclipsed conformation for butane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

65) Which of the following is a CH3-H eclipsed conformation for butane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

66) Which of the following is the correct Newman projection for the following compound showing the two methyl groups are anti?

An illustration depicts a compound that has a linear carbon chain of four carbon atoms. C 2 is wedged bonded to C l. A downward sloping dashed arrow from an eye points toward the carbon atom that is wedged bonded to C l.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

67) Which of the following is the correct Newman projection for the following compound showing the gauche conformation?

An illustration depicts a compound that has a linear carbon chain of three carbon atoms. C 1 is wedged bonded to C l. A downward sloping dashed arrow from an eye points toward the carbon atom that is wedged bonded to C l.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

68) How many substituents does the following compound have?

An illustration depicts a compound with a linear carbon chain of seven carbon atoms. C 2 is bonded to an ethyl group. C 5 is bonded to a methyl group.

A) one

B) two

C) three

D) four

E) none

Diff: 1

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

69) How many substituents does the following compound have?

An illustration depicts a compound with a linear carbon chain of eight carbon atoms. C 3 is bonded to a methyl group. C 4 is bonded to a four-carbon chain. C 5 and C 6 are bonded to an ethyl and a methyl group, respectively.

A) one

B) two

C) three

D) four

E) none

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

70) Consider the energy diagram showing the conformational analysis of propane and match the indicated position with the correct conformation below.

An illustration depicts a graph that plots energy on the vertical axis versus dihedral angle on the horizontal axis. The values on the horizontal axis range from 0 to 180. A wave with three crests and two troughs is plotted. The trough that is present between the second and third crests is indicated using an arrow.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

71) Which of the following is the lowest energy conformation of the following compound looking down the indicated bond?

An illustration depicts a compound with a SMILES string of CC(C)C(C)C. A horizontal dashed arrow from an eye points towards the C 2 atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

72) Which of the following is the highest energy conformation of the following compound looking down the indicated bond?

An illustration depicts a compound with a SMILES string of CCC(C)C. A downward sloping arrow from the eye points toward the C 3 atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

73) Which of the following is the highest energy conformation of the following compound looking down the indicated bond?

An illustration depicts a compound with a SMILES string of CCC(C)Cl. A downward sloping arrow from an eye points toward the C 3 atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

74) Which of the following is the highest energy conformation of the following compound looking down the indicated bond?

An illustration depicts a compound with a SMILES string of CC(C)C(C)C. A horizontal dashed arrow from an eye points toward the C 2 atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

75) Which of the following cycloalkanes has the most angle strain?

An illustration depicts five cycloalkanes. The first cycloalkane has a SMILES string of C1CC1. The second cycloalkane has a SMILES string of C1CCC1. The third cycloalkane has a SMILES string of C1CCCC1. The fourth cycloalkane has a SMILES string of C1CCCCC1. The fifth cycloalkane has a SMILES string of C1CCCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.9 Discuss strain in cycloalkanes

76) Which of the following cycloalkanes has the least angle strain?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.9 Discuss strain in cycloalkanes

77) Which of the following is a boat conformation of cyclohexane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.10 Describe the chair and boat conformations of cyclohexane including a comparison of their torsional strains

78) Which of the following is a chair conformation of cyclohexane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.10 Describe the chair and boat conformations of cyclohexane including a comparison of their torsional strains

79) How many substituents does the following compound have?

An illustration depicts a compound which has a linear carbon chain of seven carbon atoms. C 2 is bonded to an ethyl group. C 4 is bonded to a carbon atom which is further bonded to two methyl groups.

A) none

B) one

C) two

D) three

E) four

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

80) Which of the following is a chair conformation of the following substituted cyclohexane?

An illustration depicts a cyclohexane compound with a SMILES string of CC1CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation

81) For the following cyclohexene identify each substituent as axial or equatorial.

An illustration depicts the chair conformation of cyclohexane in which C 1 is bonded to a bromine atom and C 4 is bonded to a chlorine atom.

A) Br = axial; Cl = axial

B) Br = axial; Cl = equatorial

C) Br = equatorial; Cl = equatorial

D) Br = equatorial; Cl = axial

E) Br = neither; Cl = neither

Diff: 1

Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation

82) Identify the cyclohexane chair conformation with an axial ethyl substituent and equatorial methyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation

83) Identify the correct chair conformation of cyclohexane showing all the equatorial hydrogen atoms.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation

84) Which of the following illustrates an axial OH?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation

85) Which of the following illustrates a correctly positioned equatorial OH?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation

86) Identify the correct chair conformation of cyclohexane showing all the axial hydrogen atoms.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation

87) How many substituents does the following compound have?

An illustration depicts a compound with a linear carbon chain of eight carbon atoms. From left to right, C 2 is bonded to a methyl group. The C 4 is bonded to a carbon atom which is further bonded to two methyl groups. The C 6 is bonded to an ethyl group.

A) none

B) one

C) two

D) three

E) four

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

88) Identify the correct chair confirmations of the following compound and then indicate which one is more stable.

An illustration depicts a compound with a SMILES string of C1CCC(CC1)O.

An illustration depicts three chair conformations of a compound. In the first structure, an axial O H is present at C 5. In the second structure, an axial O H is present at C 6. In the third structure, an equatorial O H is present at C 6.

A) I and II are correct chair structures and I is most stable

B) I and II are correct chair structures and II is most stable

C) I and III are correct chair structures and III is most stable

D) II and III are correct chair structures and II is most stable

E) II and III are correct chair structures and III is most stable

Diff: 2

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored

89) Identify the correct chair confirmations of the following compound and then indicate which one is more stable.

An illustration depicts a compound with a SMILES string of CC(C)C1CCCCC1.

A) I and II are correct chair structures and I is most stable

B) I and II are correct chair structures and II is most stable

C) I and III are correct chair structures and III is most stable

D) II and III are correct chair structures and II is most stable

E) II and III are correct chair structures and III is most stable

Diff: 2

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored

90) Which is the most stable chair conformation of the following compound?

An illustration depicts a compound having a six membered ring with five carbon atoms and an oxygen atom. The C 4 is bonded to a carbon atom which is further bonded to two methyl groups.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored

91) Which is the most stable chair conformation of the following compound?

An illustration depicts a compound with a SMILES string of CC(C)C1CCCNC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored

92) Which is the most stable chair conformation of the following compound?

An illustration depicts a compound with a SMILES string of CCC1CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored

93) Identify the other chair conformation of the following compound.

An illustration depicts a chair conformation of a six membered compound with two oxygen atoms and four carbon atoms, one at first and the other at third position. An ethyl group at C 5 is in up position.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored

94) Identify the correct chair confirmations of the following compound and then indicate which one is more stable.

An illustration depicts a compound with a SMILES string of C1CCC(CC1)S.

An illustration depicts three chair conformations of a compound with a SMILES string of C1CCC(CC1)S. The first structure depicts a chair conformation with axial S H at C 5. The second structure depicts a chair conformation with axial S H at C 6. The third structure depicts a chair conformation with equatorial S H at C 5.

A) I and II are correct chair structures and I is most stable

B) I and II are correct chair structures and II is most stable

C) I and III are correct chair structures and III is most stable

D) II and III are correct chair structures and II is most stable

E) II and III are correct chair structures and III is most stable

Diff: 2

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored

95) Identify the correct chair confirmations of the following compound and then indicate which one is least stable.

An illustration depicts a compound with a SMILES string of CC1CCSCC1.

A) I and II are correct chair structures and I is least stable

B) I and II are correct chair structures and II is least stable

C) I and III are correct chair structures and I is least stable

D) II and III are correct chair structures and II is least stable

E) II and III are correct chair structures and III is least stable

Diff: 2

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored

96) Identify the most stable chair conformation of the most stable isomer of 1,3,5-trimethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

97) Identify the most stable chair conformation of the most stable isomer of 1-ethyl-3-isopropylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

98) Identify the most stable chair conformation of the most stable isomer of 1,4-diethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

99) Identify the least stable chair conformation of the most stable isomer of 1,4-diethylcyclohexane

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

100) Identify the most stable chair conformation of the most stable isomer of 1,2,4-trimethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

101) Identify the least stable chair conformation of the most stable isomer of 1,2,4-trimethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

102) Which of the following is the lowest energy chair conformation of the following cyclohexane?

An illustration depicts a cyclohexane ring in which C 1 is wedge bonded to a methyl whereas the C 2 and C 4 are each dash bonded to a methyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

103) Which of the following is the lowest energy chair conformation of the following cyclohexane?

An illustration depicts a cyclohexane ring in which C 1 and C 5 are each wedged bonded to a methyl group. The C 3 is dash bonded to a methyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

104) Identify the most stable chair conformation of the most stable isomer of 1-ethyl-2,4-dimethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

105) Identify the least stable chair conformation of the most stable isomer of 1-ethyl-2,4-dimethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

106) On each chair structure identify the relationship of the substituents as cis or trans?

An illustration depicts two chair conformations of cyclohexane. In the first structure, C 1 and C 6 are each axially bonded to a methyl group. In the second structure, C 2 and C 6 are each equatorially bonded to a methyl group.

A) I = trans; II = trans

B) I = cis; II = cis

C) I = trans; II = cis

D) I = cis; II = trans

E) not possible to tell while in a chair structure

Diff: 1

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

107) On each chair structure identify the relationship of the substituents as cis or trans?

An illustration depicts two chair conformations of cyclohexane. In the first structure, C 1 is axially bonded to a methyl group whereas the C 4 is equatorially bonded to a methyl group. In the second structure, C 2 is equatorially bonded to a methyl group whereas the C 6 is axially bonded to a methyl group.

A) I = trans; II = trans

B) I = cis; II = cis

C) I = trans; II = cis

D) I = cis; II = trans

E) not possible to tell while in a chair structure

Diff: 1

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

108) On each chair structure identify the relationship of the substituents as cis or trans?

An illustration depicts two chair conformations of cyclohexane. In the first structure, an ethyl group at C 1 is at equatorial position. The C 4 is equatorially bonded to a methyl group. In the second structure, an ethyl group at C 2 is at axial position. The C 6 is axially bonded to a methyl group.

A) I = trans; II = trans

B) I = cis; II = cis

C) I = trans; II = cis

D) I = cis; II = trans

E) not possible to tell while in a chair structure

Diff: 1

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

109) On each chair structure identify the relationship of the substituents as cis or trans?

An illustration depicts two chair conformations of cyclohexane. In the first structure, an ethyl group at C 1 is at equatorial position. The C 3 is equatorially bonded to a methyl group. In the second structure, an ethyl group at C 2 is at equatorial position. The C 5 is axially bonded to a methyl group.

A) I = trans; II = trans

B) I = cis; II = cis

C) I = trans; II = cis

D) I = cis; II = trans

E) not possible to tell while in a chair structure

Diff: 1

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

110) Identify the most stable conformation of trans-1,4-diethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

111) Identify the most stable chair conformation of cis-1,4-diethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

112) Which of the following substituted cyclohexanes is most stable?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

113) Which of the following substituted cyclohexanes is most stable?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

114) Which of the following substituted cyclohexanes is most stable?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

115) Identify the lowest energy chair conformation of the most stable isomer of 4-isopropyl-1,2-dimethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

116) How many substituents does the following compound have?

An illustration depicts a compound with a SMILES string of CCC(CC)C(C)C.

A) one

B) two

C) three

D) four

E) none

Diff: 1

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

117) How many substituents does the following compound have?

An illustration depicts a compound with a linear carbon chain of nine carbon atoms. From left to right, C 2 is bonded to a methyl group, C 3 is bonded to another methyl group and C 7 is bonded to a carbon atom which is then bonded to three methyl groups.

A) one

B) two

C) three

D) four

E) five

Diff: 2

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic

118) What is the total energy cost associated with the compound below adopting the shown conformation?

An illustration depicting a staggered Newman projection of a compound is as follows:
The compound has an inverted Y shape at the front and sphere at the back. Front half: The substituents in clockwise direction reads, H, C H 3, and H. Back half: The substituents in clockwise direction reads, C H 3, H and H.

A) 3.8 kJ/mol

B) 4 kJ/mol

C) 6 kJ/mol

D) 11 kJ/mol

E) 18 kJ/mol

Diff: 1

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

119) What is the total energy cost associated with the compound below adopting the shown conformation?

An illustration depicting Newman projection of a compound is as follows:
The compound has an inverted Y shape at the front and sphere at the back. The substituents of front and back carbon lie close to each other. Front half: The substituents in clockwise direction reads, H, H, and C H 3. Back half: The substituents in clockwise direction reads, H, H, and C H 3.

A) 3.8 kJ/mol

B) 4 kJ/mol

C) 6 kJ/mol

D) 11 kJ/mol

E) 19 kJ/mol

Diff: 2

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

120) What is the total energy cost associated with the compound below adopting the shown conformation?

An illustration depicting Newman projection of a compound is as follows:
The compound has an inverted Y shape at the front and sphere at the back. The substituents of front and back carbon lie close to each other. Front half: The substituents in clockwise direction reads, C H 3, H and H. Back half: The substituents in clockwise direction reads, H, C H 3, and H.

A) 3.8 kJ/mol

B) 11 kJ/mol

C) 14 kJ/mol

D) 16 kJ/mol

E) 18 kJ/mol

Diff: 3

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

121) What is the total energy cost associated with the compound below adopting the shown conformation?

An illustration depicting Newman projection of a compound is as follows:
The compound has an inverted Y shape at the front and sphere at the back. The substituents of front and back carbon lie close to each other. Front half: The substituents in clockwise direction reads, C H 3, H and C H 3. Back half: The substituents in clockwise direction reads, H, C H 3, and C H 3.

A) 6 kJ/mol

B) 11 kJ/mol

C) 19 kJ/mol

D) 23 kJ/mol

E) 25 kJ/mol

Diff: 3

Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

122) Identify the lowest energy conformation of butane as a Newman projection looking down the C2-C3 bond.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

123) Which of the following is a the most stable conformation of cyclohexane?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 4.10 Describe the chair and boat conformations of cyclohexane including a comparison of their torsional strains

124) Which of the following is a the least stable conformation of cyclohexane?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.10 Describe the chair and boat conformations of cyclohexane including a comparison of their torsional strains

125) Identify the highest energy conformation of butane as a Newman projection looking down the C2-C3 bond.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

126) For the following cyclohexene, identify each substituent as axial or equatorial.

An illustration depicts the chair conformation of cyclohexane in which C 1 is bonded to a fluorine atom and C 4 is bonded to a chlorine atom. Both are bonded in the plane of ring.

A) F = axial; Cl = axial

B) F = axial; Cl = equatorial

C) F = equatorial; Cl = equatorial

D) F = equatorial; Cl = axial

E) F = neither; Cl = neither

Diff: 1

Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation

127) For the following cyclohexene identify each substituent as axial or equatorial.

An illustration depicts the chair conformation of cyclohexane in which C 1 is bonded to a fluorine atom in the plane of ring and C 4 is axially bonded to a bromine atom perpendicular to the carbon.

A) F = axial; Cl = axial

B) F = axial; Cl = equatorial

C) F = equatorial; Cl = equatorial

D) F = equatorial; Cl = axial

E) F = neither; Cl = neither

Diff: 1

Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation

128) Which is the least stable chair conformation of the following compound?

An illustration depicts a compound with a SMILES string of CCC1CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored

129) Which of the following is the highest energy chair conformation of the following cyclohexane?

An illustration depicts a cyclohexane ring in which C 1 is wedged bonded to a methyl whereas the C 2 and C 4 are each dashed bonded to a methyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes

130) Identify the least stable conformation of trans-1,4-diethylcyclohexane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers

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Chapter 4 Alkanes And Cycloalkanes

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