Ch.10 Test Bank Docx An Introduction to Organic Chemistry

General, Organic, and Biochemistry, 10e (Denniston)

Chapter 10 An Introduction to Organic Chemistry

1) Which of the following statements about organic compounds is FALSE?

A) Organic compounds are only synthesized by living systems.

B) Organic compounds are carbon-containing compounds.

C) Organic compounds contain covalent bonds.

D) The carbon atoms in organic compounds may be arranged in chains or rings.

E) Structural subunits called functional groups are responsible for the chemical behavior of organic compounds.

2) Which of the following best describes molecules related as conformational isomers?

A) same molecular formulas but different bonding patterns between atoms

B) different molecular formulas but the same connections between atoms

C) same molecular formulas, the same connections between atoms, but different spatial arrangement of atoms due to rotation around bonds

D) same molecular formulas but different cis-trans arrangement of atoms

E) different molecular formulas and different bonding patterns

3) Which bonding pattern is NOT typical of carbon atoms in organic compounds?

A)

B)

C)

D)

E)

4) Which type of compound is NOT classified as an aliphatic hydrocarbon?

A) alkyne

B) aromatic

C) cycloalkane

D) alkene

E) alkane

5) Which compound is classified as an ether?

A)

B)

C)

D)

E)

6) The carbonyl group is a functional group found in many different types of compounds. What is the general structure of the carbonyl group?

A)

B)

C)

D)

E)

7) Which statement concerning the two compounds shown below is FALSE?

A) Compound A and compound B are both organic compounds.

B) Compound A and compound B are both hydrocarbons.

C) Compound B has stronger intermolecular forces than compound A.

D) Compound A is likely a gas at room temperature and compound B is likely a liquid at room temperature.

E) Compound B has a higher boiling point than compound A.

8) What is the name of the compound whose condensed formula is CH3(CH2)5CH3?

A) propane

B) pentane

C) hexane

D) heptane

E) 1,5-dimethylpentane

9) Benzene may be represented by the line formula below. What is the molecular formula of benzene?

A) C12H6

B) C6H12

C) C6H6

D) C6H14

E) C6

10) Which of the following is NOT a characteristic associated with undecane, an 11-carbon straight chain alkane?

A) hydrogen bonding

B) low water solubility

C) density less than water

D) flammable liquid

E) nonpolar

11) The functional group shown below is found in what type of compound?

A) alcohols

B) ketones

C) carboxylic acids

D) esters

E) aldehydes

12) What is the classification of the carbon atom that is bonded to the -OH group in menthol?

A) primary

B) secondary

C) tertiary

D) quaternary

E) pentary

13) An alkane used as a lubricant contains 25 carbon atoms. How many hydrogen atoms are present in its structure?

A) 25

B) 27

C) 50

D) 52

E) It is impossible to predict.

14) The structure of an organic compound may be represented in several different ways. Which formula for an organic compound explicitly shows all of the atoms and bonds in a molecule?

A) molecular formula

B) condensed formula

C) structural formula

D) patterned formula

E) line formula

15) Which correctly describes the geometry and bond angles around the indicated carbon in the structure below?

A) trigonal planar; 120°

B) tetrahedral, 109.5°

C) trigonal pyramidal, 109.5°

D) tetrahedral, 90°

E) tetravalent, 120°

16) Which of the following compounds would be named 3-ethyl-2-methylhexane?

A)

B)

C)

D)

E) (CH3)2CHCH2CH2(CH2CH3)2

17) How does an alkyl group differ from its parent alkane?

A) An alkyl group has a larger structure than its parent alkane.

B) An alkyl group contains one more hydrogen atom than its parent alkane.

C) An alkyl group contains one less carbon atom than its parent alkane.

D) An alkyl group contains one less hydrogen atom than its parent alkane.

E) There is no difference between an alkyl group and its parent alkane.

18) Which alkyl group is a secondary alkyl group?

A)

B)

C)

D)

E) All of these are correct.

19) Consider the compound 4-ethyl-2,2-dimethylhexane, shown below. What classification best describes the fourth carbon atom in this six-carbon parent chain?

A) primary

B) secondary

C) tertiary

D) quaternary

E) It is impossible to determine without knowing the structural formula.

20) Which of the following is 1-chloro-3-methylbutane?

A)

B)

C)

D)

E)

21) What is the molecular formula of the simplest alkane capable of having constitutional isomers?

A) CH4

B) C2H6

C) C3H8

D) C4H10

E) C5H12

22) How many constitutional isomers are possible for the molecular formula C5H12?

A) one

B) three

C) four

D) five

E) six

23) Which of the following properly describes constitutional isomers?

A) organic compounds with different molecular formulas

B) compounds with the same molecular formula, but a different order of attachment of atoms

C) compounds with the same molecular formula and order of attachment of atoms, but a different spatial arrangement of atoms

D) compounds with the same number of hydrogens, but a different number of carbons

E) compounds with the same number of carbons, but a different number of hydrogens

24) A cycloalkane molecule contains 8 carbon atoms. How many hydrogen atoms are present in the molecule?

A) 4

B) 8

C) 14

D) 16

E) 18

25) How does the molecular formula of a cycloalkane differ from that of the corresponding alkane?

A) The alkane has two fewer hydrogen atoms in its formula.

B) The cycloalkane has one fewer hydrogen atom in its formula.

C) The cycloalkane has one fewer carbon in its formula.

D) The cycloalkane has two fewer hydrogen atoms in its formula.

E) The alkane has two more carbon atoms in its formula.

26) What is the proper name for the compound shown below?

A) dimethylcyclohexane

B) trans-1,3-methylhexane

C) 1-methyl-3-methyl-cis-cyclohexane

D) cis-1,3-dimethylcyclohexane

E) trans-1,3-dimethylcyclohexane

27) What is the structure of trans-1,3-dibromocyclohexane?

A)

B)

C)

D)

E)

28) Eicosane is the name of the organic compound with the condensed formula CH3(CH2)18CH3. What does the prefix "eicos" specifically indicate about the structure of this compound?

A) It is an alkane.

B) It is a saturated hydrocarbon.

C) It contains a straight chain of carbons.

D) It is aliphatic.

E) It contains 20 carbons in a continuous chain.

29) What term is used to describe the various spatial arrangements of a molecule formed by rotation around C—C single bonds?

A) geometric isomers

B) conformations

C) constitutional isomers

D) enantiomers

E) structural isomers

30) How do the different conformations of an alkane molecule arise?

A) through C—C bond cleavage

B) by rotation about C—C single bonds

C) through oxidation of C—C bonds

D) by rearrangement of the order of attachment of atoms in the molecule

E) by combustion and halogenation reactions

31) The chair and boat conformations of cyclohexane are shown below. Which statement best explains why the chair conformation is more stable than the boat conformation?

A) The hydrogen atoms in the chair conformation are all staggered, which minimizes the repulsion of the bonding electrons.

B) The carbon atoms in the chair conformation are all eclipsed, which provides for the ideal bond angle of 109.5°.

C) The carbon atoms in the chair conformation are closer together than in the boat conformation, which provides for stronger C-C bonds.

D) The hydrogen atoms in the chair conformation are closer together than in the boat conformation, which provides for stronger C-H bonds.

E) The C-C bonds in the chair conformation are all staggered, which maximizes the energy of the molecule.

32) The name of an organic compound is 2-methyl-4-propyloctane. What information about the structure of this compound is FALSE?

A) It is a branched alkane.

B) There are eight carbons in the parent chain.

C) There is a one-carbon alkyl group on carbon 2 of the parent chain.

D) There is a three-carbon alkyl group on carbon 4 of the parent chain.

E) None of the above statements is false.

33) What additional condition or reagent is necessary for methane to react with chlorine according to the reaction equation shown below?

CH4 + Cl2 → CH3Cl + HCl

A) enzyme

B) water

C) light or high temperature

D) acid or base

E) complete darkness

34) The large number of organic compounds is due in part to the ability of these compounds to form constitutional isomers. Which of the following pairs of compounds are related as constitutional isomers?

A)

B)

C)

D)

E)

35) The compound shown below can be made from the halogenation reaction of what compound?

A) propane

B) hexane

C) pentane

D) benzene

E) 1-methylbutane

36) Which of the following statements concerning conformational isomers is FALSE?

A) Conformational isomers are different spatial arrangements of the same molecule, formed by rotation around single bonds.

B) Conformational isomers rapidly interconvert, and cannot be physically separated from each other.

C) The staggered and the eclipsed conformation are two types of conformational isomers of alkanes.

D) The staggered conformation is more stable than the eclipsed conformation, because in the staggered conformation electron repulsion is maximized.

E) The boat conformation and the chair conformation are two conformational isomers of cyclohexane; the chair conformation is the more stable of the two.

37) What type(s) of carbon-carbon bonds are never found in a saturated hydrocarbon?

A) single bonds

B) single and double bonds

C) double and triple bonds

D) single, double, and triple bonds

E) None of the choices are correct.

38) Traces of chloroform, CHCl3, were found in the trunk of a car of a Florida woman who was charged in the death of her child. Which of the following best represents the order of attachment of the atoms in chloroform?

A)

B)

C)

D)

E) None of the choices are correct.

39) What class of organic compounds contains the structure shown below?

A) aliphatic

B) isotopic

C) alkene

D) alkyne

E) aromatic

40) Butanone (structure shown) may be classified as what type of compound?

A) aldehyde

B) ketone

C) ether

D) carboxylic acid

E) ester

41) What functional groups are shown below?

A) alkoxy, amino

B) carbonyl, aldehyde

C) hydroxyl, ammonia

D) carbonyl, amino

E) None of the choices are correct.

42) What is the molecular formula of butane?

A) C3H8

B) C4H8

C) C4H10

D) C2H6

E) None of the choices are correct.

43) Which name describes a three-carbon alkane?

A) pentane

B) butane

C) propane

D) heptane

E) methane

44) Which of the following is the condensed formula of 3-methylheptane?

A) CH3CH2CH(CH3)CH2CH2CH2CH3

B) CH3CH2CH2(CH3)CH2CH2CH2CH3

C) CH3CH(CH3)CH2CH2CH2CH2CH3

D) CH3(CH3)CHCH2CH2CH2CH3

E) None of the choices are correct.

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

A) 2-bromo-2-methylpropane

B) 2-bromoisobutane

C) 2,2-dibromomethylpropane

D) 2-methyl-2-bromopropane

E) bromomethylbutane

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

A) 2,4,4-trimethylpentane

B) 2,2,4-octane

C) 2,2,4-trimethylpentane

D) trimethylpentane

E) None of the choices are correct.

47) Which compound is NOT an isomer with the molecular formula C5H12?

A)

B)

C)

D)

E) All of these are correct.

48) What is the IUPAC name of the compound below?

A) methylhexane

B) methylcyclohexane

C) toluene

D) hexylmethane

E) methylbenzene

49) Methane reacts with oxygen in a combustion reaction to produce carbon dioxide and water. How many moles of water are produced by the complete combustion of one mole of methane?

A) 1

B) 2

C) 3

D) 4

E) 5

50) What is the balanced equation for the complete combustion of cyclooctane?

A) C8H18 + 12O2 → 8CO2 + 9H2O

B) C8H16 + O2 → CO2 + H2O

C) 2C8H12 + 24O2 → 16CO2 + 12H2O

D) C8H16 + 12O2 → 8CO2 + 8H2O

E) C8H16 + 8O2 → 8CO + 8H2O

51) In 1828, Friedrich Wöhler carried out the first synthesis of an organic compound from inorganic substances. What compound did he accidentally make?

A) glucose

B) urea

C) ammonium cyanate

D) aspirin

E) formaldehyde

52) What is the source of most of the synthetic organic compounds that are used today?

A) methane

B) trees

C) petroleum

D) natural gas

E) coal

53) Which of the following is NOT a typical property of inorganic compounds?

A) high boiling point

B) flammable

C) water-soluble

D) rapid reactions

E) high melting point

54) The reaction shown below can be used to prepare alkyl halides. Which of the following best describes the type of reaction illustrated?

A) addition

B) substitution

C) elimination

D) combustion

E) condensation

55) Which structural formula is represented by the condensed formula shown below?

CH2BrCH2CH(CH3)2 

A)

B)

C)

D)

E)

56) Which functional group is found in alcohols?

A) carboxyl

B) carboxy

C) amino

D) carbonyl

E) hydroxyl

57) Functional groups are primarily responsible for the chemical properties of molecules in which they are found. Which of the following compounds have the same functional group, and would therefore have the same chemical properties?

A) A and D

B) B and C

C) B and D

D) A, B, and D

E) B, C, and D

58) What is the correct classification for the compound shown below?

A) alcohol

B) aldehyde

C) carboxylic acid

D) ester

E) ketone

59) What is the correct classification for the compound shown below?

A) alcohol

B) ether

C) carboxylic acid

D) amine

E) ketone

60) What is the correct classification for the compound shown below?

A) alcohol

B) ether

C) amide

D) amine

E) alkene

61) What word best describes the geometry (shape) around a carbon atom that has four single bonds to neighboring atoms?

A) tetrahedral

B) planar

C) regular

D) linear

E) unsaturated

62) Which of the following molecular formulas is not that of an alkane or cycloalkane?

A) C6H6

B) C6H12

C) C5H12

D) C3H6

E) C3H8

63) Which is the correct order of melting points for the following alkanes, from highest temperature to lowest temperature?

A) nonane > hexane > methane > ethane

B) hexane > nonane > ethane > methane

C) nonane > hexane > ethane > methane

D) nonane > ethane > hexane > methane

E) methane > ethane > hexane > nonane

64) What is the name of the alkyl group represented by the structure below?

A) acetyl

B) dimethyl

C) propyl

D) ethanyl

E) ethyl

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

A) 2-chloromethane

B) 2-chloropropane

C) 1-methyl-1-chloroethane

D) 1,1-chloromethylethane

E) 2-chloroethane

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

A) 2-ethylbutane

B) 2-methyl-2-ethylpropane

C) 3-methylpentane

D) trimethylpropane

E) 2-methyl-diethylmethane

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

A) 3-ethylpentane

B) 3-methylheptane

C) 1,4-dimethylpentane

D) 3-ethylheptane

E) 2-methyl-diethylmethane

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

A) dibromopentane

B) 2,4-dibromopentane

C) 2,4-dibromohexane

D) 2,5-dibromohexane

E) 1-bromo-2,5-methylbromopentane

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

A) 2,2-dimethylpropane

B) 2-methylbutane

C) dimethylbutane

D) 2-hydro-2-methylbutane

E) isopropylethane

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

A) 2,2-dimethylpropane

B) 2-methylbutane

C) dimethylbutane

D) tetramethylethane

E) 2,2,2-trimethylmethane

71) Molecules that have the same molecular formula, but have different structures are known as which of the following?

A) allotropes

B) isotopes

C) conformers

D) isomers

E) alkanes

72) Which compound is an isomer of 2-methylpropane?

A) 2-chloropropane

B) 2,2-dimethylpropane

C) propane

D) cyclobutane

E) butane

73) Which compound is an isomer of pentane?

A) 2-methylpentane

B) ethylcyclopropane

C) 2,2-dimethylpropane

D) cyclopentane

E) methylcyclobutane

74) Which compound is an isomer of 1,1-dibromoethane?

A) Br2CHCH3

B) CH2BrCH2Br

C) CH3CHBr2

D) CHBr2CHBr2

E) CH3BrCH3Br

75) Which compound is an isomer of butane?

A) cyclobutane

B) CH3CH(CH3)2

C) benzene

D) CH3CHBrCH2CH3

E) 2,2-dimethylpropane

76) Of the structures shown, which are related as constitutional isomers?

A) 1 and 3

B) 2 and 3

C) 3 and 4

D) Both 1 and 3 and 2 and 3 are correct.

E) 1 and 3, 2 and 3, and 3 and 4 are all related.

77) Which of the following compounds are related as geometric isomers?

A) 1 and 2

B) 1 and 3

C) 1 and 4

D) 2 and 3

E) All are related as geometric isomers.

78) Which of the following is the monohalogenated product that results when cyclopentane undergoes chlorination according to the reaction below?

A)

B)

C)

D)

E)

79) Which equation properly represents the complete combustion of propane, C3H8?

A) C3H8 + 7O2 → 3CO2 + 8H2O

B) C3H8 + 5O2 → 3CO2 + 4H2O

C) C3H8 + 10O → 3CO2 + 4H2O

D) C3H8 + 7O → 3CO + 4H2O

E) 2C3H8 + 7O2 → 6CO + 8H2O

80) Which of the following is a possible product of the halogenation reaction shown below?

A)

B)

C)

D)

E) All of the compounds are possible products.

81) Which of the following is a correct description of saturated hydrocarbons?

A) contain only single carbon-carbon bonds

B) contain only double carbon-carbon bonds

C) contain a mixture of single and double carbon-carbon bonds

D) contain a mixture of double and triple carbon-carbon bonds

E) contain a mixture of single, double, and triple carbon-carbon bonds

82) Which one of the following structures represents an unstable organic compound that is not likely to exist?

A)

B)

C)

D) CH2=CHCH2CH3

E) CH3CH2CH(CH3)2

83) A chemist needs to reflux a reaction mixture at a high temperature. This requires the use of a high-boiling organic solvent. Of the following solvents that are available for use, which would have the highest boiling point, and therefore should be used as the solvent in the reaction?

A)

B)

C)

D)

E) CH4

84) Which compound(s) below contain substituents that are trans?

A) A

B) B

C) C

D) D

E) A and B

85) Which of the following is the correct line formula for methylbutane?

A)

B)

C)

D)

E)

86) What is the molecular formula and name of the following compound?

A) C4H9Br, 3-bromobutane

B) C5H11Br, 2-bromopentane

C) C4H8Br, 2-bromobutane

D) C4H9Br, 2-bromobutane

E) C4H8Br, 3-bromobutane

87) How many secondary and tertiary carbons, respectively, are in the following compound?

A) 2, 4

B) 2, 3

C) 3, 3

D) 3, 4

E) 5, 3

88) What is the proper name of the following compound?

A) trans-dichloropentane

B) cis-dichlorocyclopentane

C) trans-1,2-dichlorocyclopentane

D) staggered-1,2-dichlorocyclopentane

E) anti-1,2-chlorocyclopentane

89) Which compound(s) below contain substituents that are cis?

A) A

B) B

C) A and B

D) C and D

E) A, C, and D

90) Urea, shown below, is an isomer of ammonium cyanate, NH4OCN.

91) When dissolved in water, inorganic compounds tend to be better conductors of electricity than organic compounds.

92) Organic compounds tend to have higher boiling points than inorganic compounds.

93) Organic compounds tend to be more soluble in hexane than inorganic compounds.

94) The carboxyl functional group is found in all ketones.

95) Alkanes are more soluble in water than in nonpolar solvents.

96) The condensed formula of a compound conveys the same information as the structural formula, but in a more concise form.

97) The propyl group is CH3CH2CH2–.

98) There is only one stable alkane of formula C4H10.

99) 2-Methylhexane is a constitutional isomer of hexane.

100) Hexane commonly exists in either a chair conformation or a boat conformation.

101) The chair conformation of cyclohexane is more stable than the boat conformation.

102) Carbon monoxide may be produced in the partial (incomplete) combustion of methane.

103) Which of the following is a passive learning strategy?

A) taking notes by hand

B) creating flash cards

C) reading the solutions manual

D) building a concept map

E) creating a visual summary

104) Students using laptops for note-taking in class demonstrate significantly worse understanding of lecture than those taking notes by hand.