Organic Chemistry, 8e (Bruice)

Chapter 3 An Introduction to Organic Compounds: Nomenclature, Physical Properties,

and Structure

1) Which of the following is a tertiary amine?

A)

B)

C)

D)

E)

Answer: E
Section: 3-7
MCAT: 19.1

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2) There are 8 isomers that have the molecular formula C5H11Br. How many of these are tertiary
alkyl bromides?
A) 0
B) 1
C) 2
D) 3
E) 8
Answer: B
Section: 3-4
MCAT: 1.1, 3.2, 6.1
GLO: G2

3) Which of the following is sec-butyl alcohol?

A) CH3CH2CH2CH2OH
B) CH3CH(OH)CH2CH3
C) (CH3)2CHCH2OH
D) (CH3)2CHOH
E) (CH3)2CHOCH3
Answer: B
Section: 3-6
MCAT: 10.1

4) Identify the number of tertiary carbons in the following structure.

A) 2
B) 3
C) 4
D) 5
E) 6
Answer: B
Section: 3-1

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5) What is the common name for the following structure?

A) isobutane
B) isopropylmethane
C) t-Butane
D) n-Butane
E) sec-Butane
Answer: A
Section: 3-2

6) Give the IUPAC name for the following structure.

A) 2-methyl-3-ethylheptane
B) 3-ethyl-2-methylheptane
C) 5-Isopropyloctane
D) 4-Isopropyloctane
E) 2-methyl-3-propylheptane
Answer: D
Section: 3-2
MCAT: 3.1

7) There is something wrong with the following name. Write the structure and correct the name:
2-ethylpropane.
Answer: The correct name is 2-methylbutane.

Section: 3-2
MCAT: 3.1

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8) Give structures for the three isomers with molecular formula C5H12 and provide the common
name of each.
Answer:

Section: 3-2
MCAT: 1.1, 3.1, 3.2

9) Provide an acceptable name for the alkane shown below.

CH3CH2CH2CH2CH2CH3
Answer: hexane or n-hexane
Section: 3-2
MCAT: 3.1

10) Provide an acceptable name for the alkane shown below.

Answer: 2,5-dimethylheptane
Section: 3-2
MCAT: 3.1

11) Provide an acceptable name for the alkane shown below.

Answer: 5-sec-butyl-2,2-dimethylnonane or
2,2-dimethyl-5-(1-methylpropyl) nonane
Section: 3-2
MCAT: 3.1

12) Provide an acceptable name for the alkane shown below.

Answer: 4-isopropyldecane or 4-(1-methlyethyl) decane

Section: 3-2
MCAT: 3.1
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13) Provide an acceptable name for the alkane shown below.

Answer: 3-ethyl-6-methyl-5-propylnonane
Section: 3-2
MCAT: 3.1

14) Provide an acceptable name for the alkane shown below.

Answer: 3-ethyl-4, 4-dimethylheptane

Section: 3-2
MCAT: 3.1

15) Draw an acceptable structure for 4-t-butyloctane.

Answer:

Section: 3-2
MCAT: 3.1

16) Draw an acceptable structure for 3-ethyl-3-methylhexane.

Answer:

Section: 3-2
MCAT: 3.1

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17) Draw an acceptable structure for 4-isopropyl-2-methylheptane.
Answer:

Section: 3-2
MCAT: 3.1

18) Draw an acceptable structure for 6-ethyl-2,6, 7-trimethyl-5-propylnonane.

Answer:

Section: 3-2
MCAT: 3.1

19) Provide an acceptable name for the alkane shown below.

Answer: 2,2,3,6-tetramethylheptane
Section: 3-2
MCAT: 3.1

20) Provide an acceptable name for the alkane shown below.

Answer: 6-ethyl-2-methyl-5-propyldecane
Section: 3-2
MCAT: 3.1

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21) Give the systematic name of the alkane shown below.

Answer: 4-ethyl-2,2,7-trimethylnonane
Section: 3-2
MCAT: 3.1

22) Give the systematic name of the alkane shown below.

Answer: 3-ethyl-4-isopropyloctane
Section: 3-2
MCAT: 3.1

23) Name the compound.

A) 2-ethyl-3-propylpentane
B) 2,3-diethylhexane
C) 4-ethyl-5-methylheptane
D) 4-methyl-3-ethylheptane
E) 4-ethyl-3-methylheptane
Answer: E
Section: 3-2

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24) Provide an acceptable name for the compound shown below.

Answer: 3,3,5-trimethylheptane
Section: 3-2

25) Provide an acceptable name for the compound shown below.

Answer: 5-ethyl-3,3-dimethyloctane
Section: 3-2
MCAT: 3.1

26) Give the systematic name of the cycloalkane shown below.

Answer: 4-butyl-1,2-dimethylcyclohexane
Section: 3-3
MCAT: 3.1

27) Draw an acceptable structure for sec-butylcyclopentane.

Answer:

Section: 3-3
MCAT: 3.1

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28) Provide the systematic name of the compound shown.

Answer: 4-butyl-1-ethyl-2-methylcycloheptane
Section: 3-3
MCAT: 3.1

29) Give the formula.

A) C8H8
B) C8H10
C) C8H12
D) C8H14
E) C8H16
Answer: D
Section: 3-3

30) Name the compound.

A) 2-cyclopentyl-4-methylhexane
B) 5-cyclopentyl-3-methylhexane
C) 1-cyclopentyl-1,3-dimethylpentane
D) 2-cyclopentyl-4-methylheptane
E) 5-cyclopentyl-3-methylheptane
Answer: A
Section: 3-3
MCAT: 3.1

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31) Determine the number of hydrogens in limonene.

A) 8
B) 10
C) 12
D) 16
E) 18
Answer: D
Section: 1-4

32) Provide an acceptable name for the compound shown below.

Answer: isobutylcycloheptane
Section: 3-3
MCAT: 3.1

33) Provide an acceptable name for the compound shown below.

Answer: 3,3-dibromo-1-chloroheptane
Section: 3-4
MCAT: 3.1

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34) Provide the common name of the compound.

A) neoheptyl chloride
B) sec-heptyl chloride
C) isoheptyl chloride
D) tert-heptyl chloride
E) n-heptyl chloride
Answer: C
Section: 3-4
MCAT: 6.1

35) Provide the IUPAC name of the compound.

A) 2-methylheptane
B) 1-chloro-5-methylhexane
C) 6-chloro-2-methylhexane
D) 1,1-dimethyl-5-chloropentane
Answer: B
Section: 3-4
MCAT: 6.1

36) What is the common name for the following structure?

A) isobutyl bromide
B) t-Butyl bromide
C) neobutyl bromide
D) sec-Butyl bromide
E) isopropyl methyl bromide
Answer: B
Section: 3-4
MCAT: 6.1

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37) Give the IUPAC name for the following compound.

A) 1-chloro-2-methylcyclohexane
B) 1-methyl-2-chlorocyclohexane
C) 1-chloro-5-methylcyclohexane
D) 1-methyl-5-chlorocyclohexane
E) 1, 2-chloromethylcyclohexane
Answer: A
Section: 3-4
MCAT: 6.1

38) Which of the following is diisopropyl ether?

A) CH3CH2CH2–O–CH2CH2CH3

B)
C) CH3CH2CH2OCH(CH3)2
D) (CH3)3COC(CH3)3
E) (CH3)2CHOCH(CH3)2
Answer: E
Section: 3-5
MCAT: 14.1

39) Draw all ethers with molecular formula C4H10O.

Answer:

Section: 3-5
MCAT: 1.1, 14.1

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40) Draw all possible constitutional isomers for C2H6O and give common names for each
structure.
Answer:

Section: 3-5, 3-6

MCAT: 1.1, 3.2, 10.1, 14.1

41) Give the IUPAC name for the following structure.

A) 3-chloro-6-methylcyclohexanol
B) 2-methyl-5-chlorocyclohexanol
C) 1-chloro-4-methylcyclohexanol
D) 5-chloro-2-methylcyclohexanol
E) 2-methyl-3-chlorocyclohexanol
Answer: D
Section: 3-6
MCAT: 6.1, 10.1

42) Which of the following compounds does not have the molecular formula C6H14O?
A) 1-hexanol
B) 2-hexanol
C) 3-methyl-2-pentanol
D) 3-methyl-3-pentanol
E) cyclohexanol
Answer: E
Section: 3-6
MCAT: 1.1, 3.2, 10.1

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43) Give the structure of isopentyl alcohol.
Answer:

Section: 3-6
MCAT: 10.1

44) Provide the systematic name of the compound shown.

Answer: 6,7-dimethyl-3-octanol
Section: 3-6
MCAT: 10.1

45) Name the structure.

Answer: 6-chloro-2-hexanol
Section: 3-6
MCAT: 6.1, 10.1

46) Provide an acceptable name for the compound shown below.

Answer: 5-ethyl-2-methylcyclohexanol
Section: 3-6
MCAT: 10.1

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47) Provide an acceptable name for the compound shown below.

Answer: N-ethyl-2-pentanamine or N-ethylpentan-2-amine

Section: 3-7
MCAT: 19.1

48) Classify the following amines as primary, secondary, or tertiary.

Answer: primary, secondary, secondary

Section: 3-7
MCAT: 19.1

49) Provide the common name of the compound.

A) tert-butyldimethylamine
B) isobutyldimethylamine
C) neobutyldimethylamine
D) sec-butyldimethylamine
E) n-butyldimethylamine
Answer: A
Section: 3-7
MCAT: 19.1

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50) Provide the IUPAC name of the compound.

A) N,N,1,1-tetramethylethanamine
B) N,N-dimethyl-2-butanamine
C) N,N,2-trimethyl-1-propanamine
D) N,N,2-trimethylpropanamine
E) N,N,2-trimethyl-2-propanamine
Answer: E
Section: 3-7
MCAT: 19.1

51) Provide the IUPAC name of the compound.

H2NCH2CH2CH2CH2OH
Answer: 4-amino-1-butanol
Section: 3-7
MCAT: 10.1, 19.1

52) Draw the structure of 3-chloro-N-ethyl-2-hexanamine.

Answer:

Section: 3-7
MCAT: 6.1, 19.1

53) Give the structure of tetramethylammonium chloride.

Answer:

Section: 3-7
MCAT: 19.1

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54) Draw the structure of N-ethyl-5-methyl-3-hexanamine.
Answer:

Section: 3-7
MCAT: 19.1

55) Fluorine is more electronegative than chlorine yet the carbon-fluorine bond in CH3-F is
shorter than CH3-Cl. Explain.
Answer: Chlorine is a larger atom than fluorine and uses a 3p rather than 2p orbital. The overlap
of a 2sp3 orbital with a 3p orbital is not as good as the overlap of a 2sp3 orbital with a 2p orbital,
causing the bond to be longer and weaker.
Section: 3-8
MCAT: 2.7
GLO: G2

56) Identify the compound with the highest bond angle.

A) the C-O-C bond in an ether
B) the C-N-C bond in a secondary amine
C) the C-N-C bond in a quaternary amine
D) the C-O-C bond in an alcohol
E) They are all equal.
Answer: C
Section: 3-8
MCAT: 10.1, 14.1, 19.1
GLO: G2

57) Identify the compound with the highest boiling point.

A) CH3CH2OCH2CH3
B) CH3CH2CH2CH2OH
C) CH3CH2CH2CH2NH2
D) CH3CH2CH2CH2Cl
E) CH3CH2CH2CH2Br
Answer: B
Section: 3-9
MCAT: 2.5

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58) Identify the compound(s) that do not have hydrogen bonding. You may choose more than
one answer.
A) CH3CH2CH2NHCH3
B) CH3CH2CH2CH2Cl
C) CH3CH2CH2CH2NH2
D) CH3CH2CH2CH2OH
E) CH3CH2CH2OCH3
Answer: B, E
Section: 3-9
MCAT: 2.5

59) Which of the following will have the lowest boiling point?
A) CH3Cl
B) CH4
C) CH2Cl2
D) CHCl3
E) CCl4
Answer: B
Section: 3-9
MCAT: 2.5

60) Which of the compounds below will form hydrogen bonds between its molecules?
A) CH3CH2CH2F
B) CH3CH2CH2CH3
C) (CH3)3N
D) CH3CH2OCH3
E) CH3NHCH2CH3
Answer: E
Section: 3-9
MCAT: 2.5
GLO: G2

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61) Which of the following has the greatest van der Waal's interaction between molecules of the
same kind?
A)

B) CH3CH2CH2CH3
C)

D) CH3CH2CH2CH2CH3
E)

Answer: D
Section: 3-9

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62) Which of the following has the lowest boiling point?
A) CH3CH2CH2CH2CH2CH3
B)

C)

D)

E) CH3CH2CH2CH2CH2CH2CH3
Answer: C
Section: 3-9
MCAT: 3.3

63) Which of the following has the greatest solubility in CH3CH2CH2CH3?

A) CH3OH
B) CH3O- Na+
C) CH3NH2
D) CH3OCH3
E) (CH3)3CH
Answer: E
Section: 3-10
MCAT: 2.5

64) Which of the following is the most soluble in H2O?

A) CH3OCH3
B) CH3CH2OH
C) CH3CH2Cl
D) CH3CH2CH3
E) CH3CHO
Answer: B
Section: 3-10
MCAT: 2.5

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65) Which of the following would have the highest boiling point?
A) CH3CH2—O—CH2CH2—O—CH3
B) CH3—O—CH2CH2CH2—O—CH3
C) HO—CH2CH2CH2CH2—OH
D) CH3CH2—O—CH2—O—CH2CH3
E)

Answer: C
Section: 3-9
MCAT: 14.1

66) Consider the three isomeric alkanes n-hexane, 2, 3-dimethylbutane, and 2-methylpentane.
Which of the following correctly lists these compounds in order of increasing boiling point?
A) 2, 3-dimethylbutane < 2-methylpentane < n-hexane
B) 2-methylpentane < n-hexane < 2, 3-dimethylbutane
C) 2-methylpentane < 2, 3-dimethylbutane < n-hexane
D) n-hexane < 2-methylpentane < 2, 3-dimethylbutane
E) n-hexane < 2, 3-dimethylbutane < 2-methylpentane
Answer: A
Section: 3-9
MCAT: 3.1, 3.3

67) What is the strongest intermolecular force present in liquid ethanol?

A) induced dipole-induced dipole
B) dipole-dipole, specifically hydrogen bonding
C) dipole-dipole, but not hydrogen bonding
D) ion-dipole
E) ion-ion
Answer: B
Section: 3-9
MCAT: 2.5, 10.1

68) Assuming roughly equivalent molecular weights, which of the following would have the
highest boiling point?
A) a tertiary amine
B) a quaternary ammonium salt
C) an alcohol
D) an ether
E) an alkyl chloride
Answer: B
Section: 3-9
MCAT: 2.5

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69) Explain why the molecule shown below has a lower boiling point than CH3CH2CH2CH3.

Answer: CH3CH2CH2CH3 has greater van der Waals forces because it has a greater contact
area than isobutane. Therefore, the boiling point of CH3CH2CH2CH3 is higher.
Section: 3-9
MCAT: 2.5, 3.3

70) Primary and secondary amines exhibit hydrogen bonding; tertiary amines do not. Explain.
Answer: The nitrogen in a tertiary amine is not attached to a hydrogen. Recall that for a
molecule to exhibit hydrogen bonding it must have a hydrogen attached to a highly
electronegative atom such as F, N, or O.
Section: 3-9
MCAT: 2.5, 19.1, 19.4

71) Explain why trimethylamine, (CH3)3N:, has a considerably lower boiling point than
propylamine CH3CH2CH2NH2, even though both compounds have the same molecular
formula.
Answer: Since hydrogen bonding is possible for propylamine and not for trimethylamine, the
boiling point is higher for propylamine.
Section: 3-9
MCAT: 19.4

72) Which of the molecules below has the higher boiling point? Briefly explain your choice.
CH3CH2CH2OH or CH3CH2OCH3
Answer: CH3CH2CH2OH has the higher boiling point since it is capable of intermolecular
hydrogen bonding.
Section: 3-9
MCAT: 2.5, 10.2, 14.1

73) Would you expect sodium chloride (NaCl) to be highly soluble in the organic solvent hexane
(CH3CH2CH2CH2CH2CH3)? Briefly explain your answer.
Answer: One would not expect NaCl to be highly soluble in hexane. NaCl is an ionic solid (i.e.,
a very polar material) while hexane is nonpolar. Nonpolar solvent molecules do not solvate ions
well. The attractions of oppositely charged ions to each other are vastly greater than the weak
attractions of the ions for the solvent.
Section: 3-10
MCAT: 1.3
GLO: G2

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74) Which compound is more soluble in water? Briefly explain your choice.
CH3OCH3 or CH3CH2OH
Answer: CH3CH2OH is more soluble in water since it can donate a hydrogen bond to water and
accept a hydrogen bond from water. CH3OCH3 can only accept a hydrogen bond from water; it
has no hydrogen which can hydrogen bond to water.
Section: 3-10
MCAT: 2.5, 10.2, 14.1
GLO: G2

75) Which compound is more soluble in water? Briefly explain your choice.
(CH3)2NH or CH3CH2CH3
Answer: (CH3)2NH is more soluble in water since it can hydrogen bond with water. Alkanes are
not capable of hydrogen bonding with water.
Section: 3-10
MCAT: 2.5, 19.4

76) Which intermolecular force is primarily responsible for the interactions among alkane
molecules?
Answer: Van der Waal's or London forces
Section: 3-9
MCAT: 2.5

77) What is polarizability and how is it related to the size of an atom?

Answer: Polarizability indicates the ease with which an electron cloud can be distorted. The
larger the atom, the more loosely its nucleus holds the electrons in its outermost shell, and the
more they can be distorted.
Section: 3-9

78) Arrange the following amines in order of increasing boiling point, lowest bp to highest bp:
(CH3)2CHCH2CH2NH2, (CH3)2CHN(CH3)2, and (CH3)2CHCH2NHCH3.
Answer: (CH3)2CHN(CH3)2 < (CH3)2CHCH2NHCH3 < (CH3)2CHCH2CH2NH2
Section: 3-9
MCAT: 19.4
GLO: G2

79) The eclipsed and staggered forms of ethane are said to differ in
A) molecular formula.
B) configuration.
C) conformation.
D) constitution.
E) structure.
Answer: C
Section: 3-11
MCAT: 3.4

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80) Which of the following is the staggered conformation for rotation about the C1—C2 bond in
the following structure?

A) I
B) II
C) III
D) IV
E) V
Answer: A
Section: 3-11
MCAT: 3.4

81) Among the butane conformers, which occur at energy minima on a graph of potential energy
versus dihedral angle?
A) gauche only
B) eclipsed and totally eclipsed
C) gauche and anti
D) eclipsed only
E) anti only
Answer: C
Section: 3-11
MCAT: 3.4

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82) Which of the following best explains the relative stabilities of the eclipsed and staggered
forms of ethane? The ________ form has the most ________ strain.
A) eclipsed; steric
B) eclipsed; torsional
C) staggered; steric
D) staggered; torsional
Answer: B
Section: 3-11
MCAT: 3.4

83) Which of the following best explains the reason for the relative stabilities of the conformers
shown?

A) I has more torsional strain.

B) I has more steric strain.
C) II has more torsional strain.
D) II has more steric strain.
Answer: D
Section: 3-11
MCAT: 3.4

84) Which of the following statements about the conformers that result from rotation about the
C2-C3 bond of butane is correct?
A) The highest energy conformer is one in which methyl groups are eclipsed by hydrogens.
B) The gauche conformer is an eclipsed one.
C) Steric strain is absent in the eclipsed forms.
D) Torsional strain is absent in the eclipsed forms.
E) none of the above
Answer: E
Section: 3-11
MCAT: 3.1

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85) Draw the Newman projection that represents the most stable conformation of 3,3-
dimethylhexane viewed along the C3-C4 bond.
Answer:

Section: 3-11
MCAT: 3.1, 3.4
GLO: G2

86) Draw the Newman projection that represents the least stable conformation of 3,3-
dimethylhexane viewed along the C3-C4 bond.
Answer:

Section: 3-11
MCAT: 3.1, 3.4

87) Draw the Newman structure for the most stable conformation of 1-bromopropane
considering rotation about the C1-C2 bond.
Answer:

Section: 3-11
MCAT: 3.4, 6.1

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88) Draw a Newman projection of the most stable conformation of 2-methylpropane.
Answer:

Section: 3-11
MCAT: 3.1, 3.4

89) Define the term conformation.

Answer: Conformations are different arrangements of the same molecule formed by rotations
about single bonds.
Section: 3-11
MCAT: 3.4

90) Use a sawhorse structure to depict the eclipsed conformer of ethane.

Answer:

Section: 3-11
MCAT: 3.1, 3.4

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91) View a butane molecule along the C2-C3 bond and provide a Newman projection of the
lowest energy conformer.
Answer:

Section: 3-11
MCAT: 3.1, 3.4

92) Provide a representation of the gauche conformer of butane.

Answer:

Section: 3-11
MCAT: 3.1, 3.4

93) Draw the Newman projection of the most stable conformation that results due to rotation
about the C2-C3 bond in 2,3-dimethylbutane.

Answer:
Section: 3-11
MCAT: 3.1, 3.4

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94) Identify the most stable conformation of butane.
A) anti
B) eclipsed
C) gauche
D) totally eclipsed
E) adjacent
Answer: A
Section: 3-11
MCAT: 3.1, 3.4

95) List the conformations in order of decreasing stability.

Answer: 6 > 3, 5 > 1, 4 > 2

Section: 3-11
MCAT: 3.4

96) Which of the following correctly ranks the cycloalkanes in order of increasing ring strain per
methylene?
A) cyclopropane < cyclobutane < cyclohexane < cycloheptane
B) cyclohexane < cyclopentane < cyclobutane < cyclopropane
C) cyclopentane < cyclobutane < cyclopentane < cyclopropane
D) cyclopentane < cyclopropane < cyclobutane < cyclohexane
E) cyclopropane < cyclopentane < cyclobutane < cyclohexane
Answer: B
Section: 3-12
MCAT: 3.1, 3.3

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97) Describe the source of angle strain and torsional strain present in cyclopropane.
Answer: The angle strain arises from the compression of the ideal tetrahedral bond angle of
109.5° to 60°. The large torsional strain occurs since all C-H bonds on adjacent carbons are
eclipsed.
Section: 3-12
MCAT: 3.1, 3.3
GLO: G2

98) Which of the following correctly lists the conformations of cyclohexane in order of
increasing energy?
A) chair < boat < twist-boat < half-chair
B) half-chair < boat < twist-boat < chair
C) chair < twist-boat < half-chair < boat
D) chair < twist-boat < boat < half-chair
E) half-chair < twist-boat < boat < chair
Answer: D
Section: 3-13
MCAT: 23.6

99) Which of the following is the most stable conformation of bromocyclohexane?

A) I
B) II
C) III
D) IV
E) V
Answer: C
Section: 3-14
MCAT: 23.6

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100) In the boat conformation of cyclohexane, the "flagpole" hydrogens are located on
A) the same carbon.
B) adjacent carbons.
C) C-1 and C-3.
D) C-1 and C-4.
E) none of the above.
Answer: D
Section: 3-13

101) Which conformer is at a local energy minimum on the potential energy diagram in the
chair-chair interconversion of cyclohexane?
A) half-chair
B) planar
C) boat
D) twist-boat
E) fully eclipsed
Answer: D
Section: 3-13
GLO: G3

102) Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha) and the
equatorial hydrogens (He).
Answer:

Section: 3-13

103) The Keq for the interconversion for the two chair forms of methylcyclohexane at 25 °C is
18. What % of the chair conformers feature an axial methyl group?
A) 95
B) 75
C) 50
D) 25
E) 5
Answer: E
Section: 3-14
GLO: G2, G4

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104) The equilibrium constant for the ring-flip of fluorocyclohexane is 1.5 at 25°C. Calculate the
percentage of the axial conformer at the temperature.
Answer: Keq = = 1.5

% axial = × 100%

= × 100%
= 40%
Section: 3-14
GLO: G2, G4

105) Which of the following describes the most stable conformation of trans-1-tert-butyl-3-
methylcyclohexane?
A) Both groups are equatorial.
B) Both groups are axial.
C) The tert-butyl group is equatorial and the methyl group is axial.
D) The tert-butyl group is axial and the methyl group is equatorial.
E) none of the above
Answer: C
Section: 3-15
MCAT: 2.4, 3.5

106) Name the compound shown below.

A) trans-1,2-dichlorocyclohexane
B) cis-1,2-dichlorocyclohexane
C) trans-1,3-dichlorocyclohexane
D) cis-1,3-dichlorocyclohexane
E) trans-1,4-dichlorocyclohexane
Answer: D
Section: 3-15
MCAT: 3.5

107) Which of the following has two equatorial alkyl substituents in its most stable
conformation?
A) 1,1-dimethylcyclohexane
B) cis-1,2-dimethylcyclohexane
C) cis-1,3-diethylcyclohexane
D) cis-1,4-diethylcyclohexane
E) trans-1,3-diethylcyclohexane
Answer: C
Section: 3-15
MCAT: 3.1, 3.3
GLO: G2
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108) Draw the most stable conformation of trans-1-tert-butyl-3-methylcyclohexane.
Answer:

or enantiomer
Section: 3-15
MCAT: 3.1, 3.3
GLO: G2

109) Draw the most stable conformer of cis-1-isopropyl-2-methylcyclohexane.

Answer:

or enantiomer
Section: 3-15
MCAT: 3.5
GLO: G2

110) Draw the most stable conformation of trans-1-isopropyl-2-methylcyclohexane.

Answer:

or enantiomer
Section: 3-15
MCAT: 3.5
GLO: G2

111) Identify the number of secondary hydrogens in the following structure.

A) 4
B) 6
C) 8
D) 10
E) 12
Answer: C
Section: 3-1

112) Identify the compound where the groups are axial and equatorial.
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A) trans-1,4-dibromocyclohexane
B) cis-1,4-dibromocyclohexane
C) cis-1,3-dibromocyclohexane
D) trans-1,2-dibromocyclohexane
E) none of the above
Answer: B
Section: 3-15
MCAT: 3.5, 6.1

113) Identify the least stable conformation for 1-tert-butyl-3-methylcyclohexane.

A) tert-butyl is axial and the methyl is equatorial.
B) tert-butyl is axial and the methyl is axial.
C) tert-butyl is equatorial and the methyl is axial.
D) tert-butyl is equatorial and the methyl is equatorial.
E) All are equally stable.
Answer: B
Section: 3-15
MCAT: 3.1, 3.5
GLO: G2

114) Draw the most stable conformer of cis-1-ethyl-2-methylcyclohexane.

Answer:

Section: 3-15
MCAT: 3.1, 3.5
GLO: G2

115) Draw the most stable conformer of trans-1-ethyl-2-methylcyclohexane.

Answer:

Section: 3-15
MCAT: 3.1, 3.5
GLO: G2

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116) Draw the most stable conformer of cis-1-ethyl-3-methylcyclohexane.
Answer:

Section: 3-15
MCAT: 3.1, 3.5
GLO: G2

117) Draw the most stable conformer of trans-1-ethyl-3-methylcyclohexane.

Answer:

Section: 3-15
MCAT: 3.1, 3.5
GLO: G2

118) Draw the most stable conformer of cis-1-ethyl-4-methylcyclohexane.

Answer:

Section: 3-15
MCAT: 3.1, 3.5
GLO: G2

119) Draw the most stable conformer of trans-1-ethyl-4-methylcyclohexane.

Answer:

Section: 3-15
MCAT: 3.1, 3.5
GLO: G2

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120) What aspect of the fused ring systems present in cholesterol make it an ideal compound to
lend rigidity to cell membranes?
Answer: The trans-fused ring systems present in cholesterol are not able to undergo chair-chair
interconversion (ring flip). This renders them a high degree of conformational rigidity.
Section: 3-16
MCAT: 3.5
GLO: G2

121) Provide the chair structure of cis-decalin, two cis-fused six-membered rings.
Answer:

Section: 3-16
GLO: G2

122) How many constitutional isomers are possible for C6H14?

A) 4
B) 5
C) 6
D) 7
E) 8
Answer: B
Section: 3-1
MCAT: 1.1, 3.2

123) If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must
it also contain?
A) n
B) n + 2
C) n - 2
D) 2n
E) 2n + 2
Answer: E
Section: 3-1

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124) Which of the following represent constitutional isomers?

A) I and II
B) I and III
C) I and IV
D) II and III
E) I, II, III and IV
Answer: E
Section: 3-0
MCAT: 2.4

125) Which of the following is true about the following compounds? You may choose more than
one answer.

A) These are identical compounds.

B) These are constitutional isomers.
C) These are conformational isomers.
D) These are different compounds.
E) There is no relationship.
Answer: A, C
Section: 3-0
MCAT: 2.4

126) Acetone has higher boiling point than propane because

A) double bond in acetone is hard to break.

B) acetone has higher molecular weight.
C) acetone exhibits dipole-dipole interactions which are stronger than van der Waal's interactions
in propane.
D) acetone exhibit hydrogen bonding which is stronger than van der Waal's interactions in
propane.
E) acetone has higher surface area.
Answer: C
Section: 3-9
MCAT: 2.5

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127) The parent chain in the following molecule is

A) pentane.
B) hexane.
C) heptane.
D) octane.
E) nonane.
Answer: C
Section: 3-11
MCAT: 3.1

128) What is the common name of the alkyl substituent present on C-2 of menthol shown below?

A) isopropyl
B) isobutyl
C) sec-butyl
D) tert-butyl
E) iso-pentyl
Answer: A
Section: 3-1
MCAT: 3.1

129) Name the following molecule.

Answer: 2-ethyl-2-methylhexan-1-ol
Section: 3-6, 3-11
MCAT: 10.1

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130) The dihedral angle between the bromo and ethyl substituents present on the adjacent
carbons of the following molecule is

A) 0°
B) 60°
C) 90°
D) 120°
E) 180°
Answer: E
Section: 3-11

131) Structure of commonly used anti-anxiety drug, valium is shown below. What are the
strongest intermolecular interactions present between molecules?

A) Van der Waals interactions

B) dipole-dipole interactions
C) hydrogen bonding
D) covalent bonding
E) ionic bonding
Answer: B
Section: 3-9
MCAT: 2.5

132) Which of the following atoms has the highest polarizability?

A) H
B) O
C) N
D) C
E) S
Answer: E
Section: 3-9
GLO: G2

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133) Draw the Newman projection of the following molecule sighting down the indicated bond?

Answer:

Section: 3-11
MCAT: 3.4

134) In the chair conformation of cyclohexane, how many hydrogen atoms are eclipsed?
A) 0
B) 2
C) 4
D) 6
E) 8
Answer: A
Section: 3-15

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135) Which of the following represents the ring flipped structure of the molecule below?

A) I
B) II
C) III
D) IV
E) V
Answer: D
Section: 3-15
MCAT: 5.1

136) How many axial hydrogens are present in this molecule?

A) 2
B) 3
C) 4
D) 5
E) 6
Answer: C
Section: 3-15

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