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Test Bank for Organic Chemistry 13th Edition by Graham

Solomons

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Book Title: Organic Chemistry

Edition: 13th Edition

Author: Graham Solomons

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Package title: Solomons Test Bank
Course Title: Solomons 13e
Chapter Number: 2

Question type: Multiple choice

1) Which of the following compounds contains polar covalent bonds?

A) S8
B) LiF
C) F2
D) CH3F
E) None of these choices.

Answer: D

Topic: Polar Covalent Bonds

Section Reference 1: 2.2
Difficulty: Easy

2) Which molecule does not have a dipole moment?

F

A) F
F F

B)

F
C)
F

D) F
E) None of these choices.

Answer: D

Topic: Molecular geometry, polarity

Section Reference 1: 2.3
Difficulty: Easy

1
3) Of the following solvents which one does not have a zero dipole moment?

A) Pentane
B) Cyclohexane
C) Diethyl ether
D) Cyclopentane
E) None of these choices.

Answer: C

Topic: Molecular geometry, polarity

Section Reference 1: 2.3
Difficulty: Easy

4) Which molecule has a zero dipole moment?

A) CH3Cl
B) CH2Cl2
C) CHCl3
D) CCl4
E) None of these choices.

Answer: D

Topic: Molecular geometry, polarity

Section Reference 1: 2.3
Difficulty: Easy

5) Which molecule would you expect to have no dipole moment (i.e.,  = 0 D) ?

A) CHF3

B)
C) :NF3

D)
E) CH2F2

Answer: B

Topic: Molecular geometry, dipole moment

Section Reference 1: 2.3
Difficulty: Easy

2
6) Which molecule has a dipole moment greater than zero?

A)

B)

C)
D) More than one of these choices.
E) None of these choices.

Answer: D

Topic: Molecular geometry, dipole moment

Section Reference 1: 2.3
Difficulty: Easy

7) Which of the following would have no net dipole moment ( = 0 D)?

A) CBr4
B) cis-1,2-Dibromoethene
C) trans-1,2-Dibromoethene
D) 1,1-Dibromoethene
E) More than one of these choices.

Answer: E

Topic: Molecular geometry, dipole moment

Section Reference 1: 2.3
Difficulty: Medium

3
8) For a molecule to possess a dipole moment, which following condition is necessary but not
sufficient?

A) three or more atoms in the molecule

B) presence of one or more polar bonds
C) a non-linear structure
D) presence of oxygen or fluorine
E) absence of a carbon-carbon double or triple bond

Answer: B

Topic: Molecular geometry, polarity

Section Reference 1: 2.3
Difficulty: Medium

9) Which molecule has a zero dipole moment?

A) SO2
B) CO2
C) CO
D) CHCl3
E) None of these choices.

Answer: B

Topic: Molecular geometry, polarity

Section Reference 1: 1.5 and 2.3
Difficulty: Easy

10) Which molecule has a zero dipole moment?

A) CO2
B) CH4
C) CH3CH3

D)
E) All of these choices.

Answer: E

Topic: Molecular geometry, polarity

Section Reference 1: 1.5 and 2.3
Difficulty: Easy

4
11) Which molecule has a dipole moment of zero?

A) CHCl3
B) CH2Cl2
C) ClHC=CH2
D) trans-ClHC=CHCl
E) None of these choices.

Answer: D

Topic: Molecular geometry, polarity

Section Reference 1: 1.5 and 2.3
Difficulty: Medium

12) Which molecule would have a dipole moment greater than zero?

A) BeCl2
B) BCl3
C) CO2
D) H2O
E) CCl4

Answer: D

Topic: Molecular geometry, polarity

Section Reference 1: 1.5 and 2.3
Difficulty: Medium

13) A non-zero dipole moment is exhibited by:

A) SO2
B) CO2
C) CCl4
D) BF3

E)

Answer: A

Topic: Molecular geometry, polarity

Section Reference 1: 1.5, 1.6 and 2.3
Difficulty: Medium

5
14) Of the following common organic solvents which one is predicted to have the smallest dipole
moment?

A) Chloroform, CHCl3
B) Acetone, (CH3)2CO
C) Dimethylsulfoxide, (CH3)2SO
D) Acetonitrile, CH3CN
E) Methanol, CH3OH

Answer: A

Topic: Molecular geometry, polarity

Section Reference 1: 1.5, 1.6, and 2.3
Difficulty: Hard

15) Which molecule(s) has/have dipole moment(s) equal to zero?

A)

B)

C)

D)
E) None of these choices have dipole moments equal to zero.

Answer: C

Topic: Molecular geometry, Polarity

Section Reference 1: 2.3
Difficulty: Easy

6
16) What alkyl groups make up the following ether?
O

A) ethyl and phenyl

B) propyl and benzyl
C) ethyl and benzyl
D) propyl and phenyl
E) None of these choices.

Answer: C

Topic: Functional groups

Section Reference 1: 2.4
Difficulty: Easy

17) What alkyl groups make up the following ketone?

Ph
O

A) Phenyl, pentyl
B) Hexyl, phenyl
C) Benzyl, hexyl
D) Benzyl, heptyl
E) None of these choices.

Answer: C

Topic: Functional groups

Section Reference 1: 2.4
Difficulty: Medium

7
18) What alkyl groups make up the following ether?

A) Isobutyl and methyl

B) Methyl and butyl
C) Ethyl and isopropyl
D) Methyl and sec-butyl
E) None of these choices.

Answer: D

Topic: Functional groups

Section Reference 1: 2.4
Difficulty: Easy

19) What alkyl groups make up the following ether?

O

A) isobutyl and propyl

B) propyl and butyl
C) ethyl and isopropyl
D) propyl and sec-butyl
E) None of these choices.

Answer: A

Topic: Functional groups

Section Reference 1: 2.4
Difficulty: Easy

8
20) What alkyl group is attached to the oxygen in the following ester?
O

A) ethyl
B) propyl
C) sec-propyl
D) isopropyl
E) None of these choices.

Answer: D

Topic: Functional groups

Section Reference 1: 2.4
Difficulty: Easy

21) What alkyl groups make up the following 3o amine?

A) sec-butyl, ethyl, propyl

B) isobutyl, isopropyl, ethyl
C) sec-butyl, ethyl, isopropyl
D) butyl, ethyl, propyl
E) None of these choices.

Answer: A

Topic: Functional groups

Section Reference 1: 2.4
Difficulty: Easy

9
22) What alkyl groups are attached to the benzene ring in the following example?
H3CH2CH2C

A) ethyl, butyl
B) ethyl, isobutyl
C) propyl, sec-butyl
D) propyl, butyl
E) None of these choices.

Answer: E

Topic: Functional groups

Section Reference 1: 2.4
Difficulty: Easy

23) What common group is attached to both the ether and 3o amine in the following molecule?
OCH2C6H5

NBn

A) benzyl
B) phenyl
C) heptyl
D) ethyl
E) None of these choices.

Answer: A

Topic: Functional groups

Section Reference 1: 2.4
Difficulty: Medium

10
24) What group makes up the following aldehyde (benzaldehyde)?
C6H5CHO

A) benzyl
B) phenyl
C) heptyl
D) ethyl
E) None of these choices.

Answer: B

Topic: Functional groups

Section Reference 1: 2.4
Difficulty: Medium

25) What functional group is present in the following compound?

Br

A) 1o alkyl halide
B) 2o alcohol
C) 2o alkyl halide
D) 1o amine
E) 3o alkyl halide

Answer: C

Topic: Functional groups

Section Reference 1: 2.5
Difficulty: Easy

11
26) Which is a 3 alkyl halide?

A) I
B) II
C) III
D) IV
E) V

Answer: B

Topic: Functional Groups

Section Reference 1: 2.5
Difficulty: Easy

12
27) Which compound(s) contain(s) tertiary carbon atom(s) ?

A) I, II, III
B) I
C) II, III
D) I, IV
E) V

Answer: D

Topic: Functional groups

Section Reference 1: 2.5
Difficulty: Medium

28) Which of these compounds is a secondary alkyl chloride?

A) CH3CH2CH2CH2CH2Cl

B)

C)
D) (CH3)2CHCHClCH3
E) Two of these choices.

Answer: E

Topic: Functional groups

Section Reference 1: 2.5
Difficulty: Medium

13
29) How many 2º alkyl bromides, neglecting stereoisomers, exist with the formula C6H13Br?

A) 4
B) 5
C) 6
D) 7
E) 8

Answer: C

Topic: Functional groups, Isomerism

Section Reference 1: 1.6 and 2.5
Difficulty: Medium

30) The number of unique open-chain structures corresponding to the molecular formula C3H5Cl
is:

A) 2
B) 3
C) 4
D) 5
E) 6

Answer: C

Topic: Isomers
Section Reference 1: 1.6 and 2.5
Difficulty: Medium

14
31) Which compound listed below is a secondary alcohol?

A)

B)

C)
D) CH3CH2CH2CH2OH
E) CH3CH2CH2OCH3

Answer: A

Topic: Functional groups

Section Reference 1: 2.6
Difficulty: Easy

32) What functional group is present in the following compound?

HO

A) 1o alcohol
B) ether
C) 2o alcohol
D) ester
E) 3o alcohol

Answer: E

Topic: Functional groups

Section Reference 1: 2.6
Difficulty: Easy

15
33) Which compound is a tertiary alcohol?

CH3
OH HO
H3CH2C O
CH3

I II III

O OH

IV V

A) I
B) II
C) III
D) IV
E) V

Answer: E

Topic: Functional groups

Section Reference 1: 2.6
Difficulty: Medium

16
34) What functional group(s) is/are present in the following compound?
OH

A) alkyne and 2o alcohol

B) alkyne and 1o alcohol
C) 2o alcohol and alkene
D) nitrile and 1o alcohol
E) alkene and 2o alcohol

Answer: A

Topic: Functional groups

Section Reference 1: 2.1 and 2.6
Difficulty: Easy

35) A tertiary carbon atom is present in which of these compounds?

A) I
B) II, IV
C) III, V
D) IV
E) All of these choices.

Answer: C

Topic: Functional groups

Section Reference 1: 2.5 and 2.6
Difficulty: Easy

17
36) What functional group(s) is/are present in the following compound?
Cl
OH

A) 1o alcohol and 2o alkyl chloride

B) ether and 2o alcohol
C) 1o alkyl chloride and 1o alcohol
D) 1o alkyl chloride and 2o alcohol
E) None of these choices.

Answer: D

Topic: Functional groups

Section Reference 1: 2.5 and 2.6
Difficulty: Easy

37) How many constitutional isomers are possible with the formula C4H10O?

A) 3
B) 4
C) 5
D) 6
E) 7

Answer: E

Topic: Functional groups, Isomerism

Section Reference 1: 1.3, 2.6, and 2.7
Difficulty: Easy

18
38) Which compound is a secondary amine?

A) CH3CH2CH2NH2

B)

C)

D)

E)

Answer: C

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

39) Which compound is a primary amine with the formula C5H13N?

A) I
B) II
C) III
D) IV
E) V

Answer: C

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

19
40) What functional group is present in the following compound?

N
H

A) 1o alkyl bromide
B) 2o amine
C) nitrile
D) 1o amine
E) 3o amine

Answer: B

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

41) What functional group is present in the following compound?

A) 1o alkyl bromide
B) 2o amine
C) nitrile
D) 1o amine
E) 3o amine

Answer: E

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

20
42) Which is a 3 amine?

A) I
B) II
C) III
D) IV
E) V

Answer: D

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

43) What functional groups are present in nicotine, an addictive substance found in tobacco?

A) two tertiary amines

B) two secondary amines
C) phenyl ring and tertiary amine
D) secondary and tertiary anime
E) none of these choices

Answer: A

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

21
44) An example of a tertiary amine is:

A) I
B) II
C) III
D) IV
E) V

Answer: E

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

45) What functional group(s) is/are present in the following compound?

NCH3
O

A) ether and 2o amine

B) ester and 3o amine
C) 3o amine
D) 3o amine and ether
E) None of these choices.

Answer: D

Topic: Functional groups

Section Reference 1: 2.7 and 2.8
Difficulty: Easy

22
46) Which compound is a ketone?

A)

B)

C)

D)

E)

Answer: B

Topic: Functional groups

Section Reference 1: 2.9
Difficulty: Easy

23
47) Which compound is an aldehyde?

A) I
B) II
C) III
D) IV
E) V

Answer: D

Topic: Functional groups

Section Reference 1: 2.9
Difficulty: Easy

24
48) What functional group is present in the following compound?

CHO

A) alcohol
B) ketone
C) aldehyde
D) ester
E) ether

Answer: C

Topic: Functional groups

Section Reference 1: 2.9
Difficulty: Medium

49) What functional group is present in the following compound?

COCH3

A) alcohol
B) ketone
C) aldehyde
D) ester
E) ether

Answer: B

Topic: Functional groups

Section Reference 1: 2.9
Difficulty: Medium

25
50) What functional group(s) is/are present in the following compound?

OHC

A) Ketone and alkene

B) Ketone and alkyne
C) Aldehyde and alkene
D) Aldehyde and alkyne
E) 1o alcohol and alkene

Answer: C

Topic: Functional groups

Section Reference 1: 2.1 and 2.9
Difficulty: Medium

51) The compound below is an adrenocortical hormone called cortisone. Which functional group
is not present in cortisone?

A) 1 alcohol
B) Ketone
C) 3 alcohol
D) Carboxylic acid
E) Alkene

Answer: D

Topic: Functional groups

Section Reference 1: 2.1, 2.6, and 2.9
Difficulty: Easy

26
52) Which functional groups are present in the following compound?
OH O

A) Alkene, 1º alcohol, ketone

B) Alkene, 2º alcohol, aldehyde
C) Alkene, 2º alcohol, ketone
D) Alkyne, 1º alcohol, aldehyde
E) Alkyne, 2º alcohol, ketone

Answer: B

Topic: Functional groups

Section Reference 1: 2.1, 2.6, and 2.9
Difficulty: Easy

53) In addition to a cycloalkane skeleton, testosterone also contains the following functional
groups:

A) Alkene, ester, tertiary alcohol

B) Alkene, ether, secondary alcohol
C) Alkene, ketone, secondary alcohol
D) Alkyne, ketone, secondary alcohol
E) Alkene, ketone, tertiary alcohol

Answer: C

Topic: Functional groups

Section Reference 1: 2.1, 2.6, and 2.9
Difficulty: Easy

27
54) The compound shown below is norethyndrel, a synthetic estrogen. It was marketed in the
first oral contraceptive under the name Enovid.

In addition to an alkane (actually cycloalkane) skeleton, the norethyndrel molecule also contains
the following functional groups:

A) Ether, alcohol, alkyne

B) Aldehyde, alkene, alkyne, alcohol
C) Alcohol, carboxylic acid, alkene, alkyne
D) Ketone, alkene, alcohol, alkyne
E) Amine, alkene, ether, alkyne

Answer: D

Topic: Functional groups

Section Reference 1: 2.1, 2.6, and 2.9
Difficulty: Medium

55) Many organic compounds contain more than one functional group. Which of the following
is/are both an aldehyde and an ether?

A) I
B) II, IV
C) V
D) I, V
E) III

Answer: A

Topic: Functional Groups

Section Reference 1: 2.7 and 2.9
Difficulty: Easy

28
56) Which is a carboxylic acid?

A) I
B) II
C) III
D) IV
E) V

Answer: E

Topic: Functional groups

Section Reference 1: 2.10
Difficulty: Easy

29
57) What functional group(s) is/are present in the following compound?

CO2H

A) 1o alcohol and ketone

B) carboxylic acid
C) ester
D) 1o alcohol and aldehyde
E) alcohol

Answer: B

Topic: Functional groups

Section Reference 1: 2.10
Difficulty: Medium

58) What functional group(s) is/are present in the following compound?

HO2C

A) 1o alcohol and ketone

B) ester
C) carboxylic acid
D) 1o alcohol and aldehyde
E) alcohol

Answer: C

Topic: Functional groups

Section Reference 1: 2.10
Difficulty: Medium

30
59) Which functional group is not contained in prostaglandin E1?

Prostaglandin E1

A) Ketone
B) 2 alcohol
C) 3 alcohol
D) Carboxylic acid
E) Alkene

Answer: C

Topic: Functional groups

Section Reference 1: 2.1, 2.6, 2.9, and 2.10
Difficulty: Medium

60) What functional group(s) is/are present in the following compound?

O

A) ether and ketone

B) carbonyl and ether
C) carboxylic acid and ether
D) ester
E) 1o alcohol

Answer: D

Topic: Functional groups

Section Reference 1: 2.10
Difficulty: Easy

31
61) Which compound is an ester?

A) I
B) II
C) III
D) IV
E) V

Answer: C

Topic: Functional groups

Section Reference 1: 2.10
Difficulty: Easy

62) What functional group is present in the following compound?

CO2CH3

A) alcohol
B) ketone
C) aldehyde
D) ester
E) ether

Answer: D

Topic: Functional groups

Section Reference 1: 2.10
Difficulty: Medium

32
63) What functional group(s) is/are present in the following compound?
CO2CH2CH3

OH

A) Ketone and 1o alcohol

B) Ether and alcohol
C) Ester and ether
D) Ester and 1o alcohol
E) 1o alcohol and aldehyde

Answer: D

Topic: Functional groups

Section Reference 1: 2.6 and 2.10
Difficulty: Medium

64) Which compound can be classified as an ester as well as a ketone?

A) I
B) II
C) III
D) IV
E) V

Answer: D

Topic: Functional groups

Section Reference 1: 2.9 and 2.10
Difficulty: Medium

33
65) Drawn below is atropine, found in Atropa belladonna, sometimes used in dilating pupils
during an eye exam. Which of the following functional groups is NOT in atropine?

A) Amine
B) Ester
C) Alcohol
D) Benzene ring
E) Ketone

Answer: E

Topic: Functional groups

Section Reference 1: 2.1, 2.6, 2.8, and 2.10
Difficulty: Hard
66) What functional group(s) is/are present in the following compound?
HO O

NHCH3

A) 1o alcohol and 2o amine

B) amide and 2o alcohol
C) nitrile and 1o alcohol
D) 2o amide and ether
E) None of these choices.

Answer: E

Topic: Functional groups

Section Reference 1: 2.6 and 2.10
Difficulty: Medium

34
67) Many bacterial cells contain functional groups that are susceptible to antibiotic drugs, but
may, over time, change their functional groups to become resistant to these drugs. What
functional group change is occurring in the transition shown below?

A) Amine to ether
B) Amine to ester
C) Amide to ester
D) Amide to ether
E) None of these choices.

Answer: C

Topic: Functional Groups

Section Reference 1: 2.10
Difficulty: Medium

68) The compound shown below is a substance called capsaicin, found in varying concentrations
in several varieties of hot peppers, and responsible for their respective degrees of “heat.” Which
functional groups are present in the molecule of capsaicin?

A) Alkene, ketone, amine, alcohol, ester

B) Alkene, ketone, alcohol, ether
C) Alkene, amine, phenol, ether
D) Ether, phenol, alkene, amide
E) Ester, phenol, alkene, amide

Answer: D

Topic: Functional groups

Section Reference 1: 2.1, 2.6, 2.7, and 2.10
Difficulty: Medium

35
69) The compound aspartame is a dipeptide that is often used as a sugar substitute. Which
functional groups are present in aspartame?

A) carboxylic acid, secondary amine, ketone, ester

B) alcohol, secondary amine, ketone, ester
C) carboxylic acid, ester, amide, secondary amine
D) ester, amide, primary amine, carboxylic acid
E) none of these choices

Answer: D

Topic: Functional groups

Section Reference 1: 2.1, 2.6, 2.7, and 2.10
Difficulty: Medium

70) What functional group(s) is/are present in the following compound?

NC NHCH3

A) 1o amine and 2o amine

B) amide and 2o amine
C) 2o amine and nitrile
D) nitrile and 1o amine
E) amide and nitrile

Answer: C

Topic: Functional groups

Section Reference 1: 2.8 and 2.11
Difficulty: Medium

71) The strongest of attractive forces is which type?

A) Dispersion forces
B) Ion-dipole
C) Dipole-dipole

36
D) Cation-anion
E) Hydrogen bonds

Answer: D

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

72) Which of these is the weakest of the intermolecular attractive forces taken individually?

A) Ion-ion
B) Dispersion forces
C) Dipole-dipole
D) Covalent bonding
E) Hydrogen bonding

Answer: B

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy
73) Which compound would you expect to have the highest melting point?

A) n-Butyl alcohol
B) Isobutyl alcohol
C) sec-Butyl alcohol
D) tert-Butyl alcohol
E) Diethyl ether

Answer: D

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

37
74) Which of the following is not found in the following substance?
CH3CH2CH2CH2CH2OH

A) Ion-ion
B) Dispersion forces
C) Dipole-dipole
D) Covalent bonding
E) Hydrogen bonding

Answer: A

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

75) Which alkane is predicted to have the highest melting point of those shown?

A) CH3CH2CH2CH3

B)
C) CH3CH2CH2CH2CH3

D)

E)

Answer: E

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

38
76) What intermolecular forces hold base pairs together in DNA?

A) Ion-ion
B) Dipole-dipole
C) Hydrogen bonds
D) Dispersion forces
E) Covalent bonds

Answer: C

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

77) Which compound would you expect to have the lowest boiling point?
A)

B)

C)

D)

E)

Answer: D

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

39
78) Which of these compounds would have the highest boiling point?

A) CH3OCH2CH2CH2OCH3
B) CH3CH2OCH2CH2OCH3
C) CH3CH2OCH2OCH2CH3

D)
E) HOCH2CH2CH2CH2CH2OH

Answer: E

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

79) Which compound would have the highest boiling point?

A) CH3CH2CH2CH2CH2CH3
B) CH3CH2OCH2CH2CH3
C) CH3CH2CH2CH2CH2OH
D) CH3CH2OCH(CH3)2
E) CH3OCH2CH2CH2CH3

Answer: C

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

80) Of the following compounds, the one with the highest boiling point is:

A) CH3CH3
B) CH3CH2Cl

C)
D) CH3CH2OH
E) CH3CH2OCH2CH3

Answer: D

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

40
81) Which compound would you expect to have the highest boiling point?

A) ethane
B) ethene
C) ethyne
D) bromoethane
E) methane

Answer: D

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

82) Which compound would you expect to have the highest boiling point?

A) ethyl alcohol
B) ethyl amine
C) chloroethane
D) water
E) ethane

Answer: D

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

83) Which of these would you expect to have the lowest boiling point?

A) CH3CH2CH2OH

B)
C) CH3OCH2CH3
D) CH3CH2CH2CH2OH
E) CH3CH2OCH2CH3

Answer: C

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

41
84) Which compound would you expect to have the lowest boiling point?

A)

B)

C)

D)

E)

Answer: C

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

85) Which compound would you expect to have the highest boiling point?

A) CH3OCH2CH2OCH3
B) CH3OCH2OCH2CH3
C) HOCH2CH2CH2CH2OH
D) CH3OCH2CH2CH2OH
E) (CH3O)2CHCH3

Answer: C

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

42
86) Which compound would have the lowest boiling point?

A) I
B) II
C) III
D) IV
E) V

Answer: A

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

87) The solid alkane CH3(CH2)18CH3 is expected to exhibit the greatest solubility in which of the
following solvents?

A) CCl4
B) CH3OH
C) H2O
D) CH3NH2
E) HOCH2CH2OH

Answer: A

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

43
88) The following substance is expected to have the lowest solubility in which of the following
solvent(s) ?

A) CCl4
B) C2H5OH
C) CHCl3
D) HOCH2CH2CH2CH2CH2CH2OH
E) The given substance is likely to be quite soluble in all of the solvents described.

Answer: A

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

89) The compound NaOH is barely soluble in ethanol. The addition of which of the following
solvents to ethanol would greatly increase the solubility of NaOH?

A) H2O
B) Et2O
C) CH2Cl2
D) Benzene
E) All of these choices.

Answer: A

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

44
90) For the functional group(s) on the following molecule what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions)?
CHO

A) a peak around 1700 cm–1

B) a peak around 3300 cm–1
C) only normal alkane absorptions
D) a peak around 2250 cm–1
E) None of these choices.

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy

91) For the functional group(s) on the following molecule what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions) ?

A) a peak around 1700 cm–1

B) a peak around 3300 cm–1
C) a peak around 1650 cm–1
D) a peak around 2250 cm–1
E) None of these choices.

Answer: C

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy

45
92) The IR spectrum of which type of compound will not show evidence of hydrogen bonding?

A) Aldehyde
B) Alcohol
C) Carboxylic acid
D) Phenol
E) Primary amine

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy

93) The IR spectrum of which type of compound generally exhibits evidence of hydrogen
bonding?

A) Aldehyde
B) Carboxylic acid
C) Alkene
D) Ester
E) Ketone

Answer: B

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy

46
94) IR evidence for the presence of the C=C would be most difficult to detect in the case of
which of these alkenes?

A)
B)

C)

D)

E)

Answer: D

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy

95) An oxygen-containing compound shows strong IR absorption at 1630-1780 cm–1 and 3200-
3550 cm–1. What type of compound is it likely to be?

A) an alcohol
B) a carboxylic acid
C) an ether
D) a ketone
E) an aldehyde

Answer: B

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

47
96) For the functional group(s) on the following molecule what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions)?
CN

A) a peak around 1700 cm–1

B) a peak around 3300 cm–1
C) a peak around 1650 cm–1
D) a peak around 2250 cm–1
E) None of these choices.

Answer: D

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

97) For the functional group(s) on the following molecule, what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions)?

HO

A) peaks around 1700 and 1650 cm–1

B) peaks around 3300 and 1710 cm–1
C) peaks around 1650 and 3300 cm–1
D) only a peak around 3300 cm–1
E) None of these choices.

Answer: C

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

48
98) For the functional group(s) on the following molecule, what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions)?

CO2H

A) peaks around 1700 and 1650 cm–1

B) a strong broad peak over 3600 to 2500 and around 1710 cm–1
C) peaks around 1650 and 3300 cm–1
D) peaks around 3300 and 1710 cm–1
E) None of these choices.

Answer: B

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

99) For the functional group(s) on the following molecule, what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions)?
Br

A) peaks around 1710 and 1650 cm–1

B) a strong broad peak over 3600 to 2500 cm–1
C) peaks around 1650 and 3300 cm–1
D) a peak around 1710 cm–1
E) None of these choices.

Answer: E

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

49
100) For the functional group(s) on the following molecule, what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions)?

A) peaks around 3300, 2150, and 1650 cm–1

B) peaks around 1710 and 1650 cm–1
C) peaks around 1650 and 3300 cm–1
D) a peak around 2250 and 3300 cm–1
E) None of these choices.

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

101) The absorption band for the O-H stretch in the IR spectrum of an alcohol is sharp and
narrow in the case of

A) a Nujol mull of the alcohol.

B) a concentrated solution of the alcohol.
C) a gas phase spectrum of the alcohol.
D) the spectrum of the neat liquid.
E) None of these choices.

Answer: C

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

50
102) A split peak for the IR absorption due to bond stretching is observed for the carbonyl group
in which of these compounds?

A) ca

B)

C)

D)

E)

Answer: E

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

103) The IR spectrum of which of the following substances is likely to show a small, but sharp
peak at 2200 cm–1?
OH
O
N
H
I II III

IV V

A) I
B) II
C) III
D) IV
E) V

Answer: E

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

51
104) An anticipated IR absorption band may not be observed because

A) it occurs outside the range of the instrument used.

B) no change occurs in the dipole moment during the vibration.
C) the absorption band is eclipsed by another.
D) the intensity is so weak that it cannot be differentiated from instrument noise.
E) All of these choices.

Answer: E

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

105) For the functional group(s) on the following molecule what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions)?

A) peaks around 1740 and 1650 cm–1

B) a strong broad peak over 3600 to 2500 cm–1
C) peaks around 1650 and 3300 cm–1
D) a peak around 1740 cm–1
E) None of these choices.

Answer: D

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

52
106) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions)?
a. NaNH 2

b. CH 3CH 2I

A) A peak around 1710 cm–1 would disappear.

B) A peak around 1710 cm–1 would appear.
C) A peak around 2150 cm–1 would disappear.
D) No change would be observed.
E) None of these choices.

Answer: C

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

107) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions)?
O
a. CH3MgBr
OH
b. H3O+

A) A peak around 1710 cm–1 would disappear and a new peak around 3300-3500 cm–1 would
appear.
B) A peak around 1710 cm–1 would disappear and a new peak around 1650 cm–1 would appear.
C) A peak around 2150 cm–1 would disappear and a new peak around 3300-3500 cm–1 would
appear.
D) No change would be observed.
E) None of these choices.

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

53
108) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions)?
a. NaH
OH OCH3
b. CH3I

A) A peak around 3300 cm–1 would disappear.

B) A peak around 1710 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
C) A peak around 2150 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
D) No change would be observed.
E) None of these choices.

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

109) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions)?

A) A peak around 3300 cm–1 would disappear.

B) A peak around 1710 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
C) A peak around 2150 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
D) No change would be observed.
E) None of these choices.

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

54
110) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions)?
OH O
PCC

A) A peak around 3300 cm–1 would disappear and nothing new would appear.
B) A new peak around 1710 cm–1 would appear and a peak around 3300 cm–1 would disappear.
C) A peak around 2150 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
D) No change would be observed.
E) None of these choices.

Answer: B

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

111) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions)?

A) A peak around 3300 cm–1 would appear and nothing new would appear.
B) A peak around 1710 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
C) A peak around 2150 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
D) No change would be observed.
E) None of these choices.

Answer: E

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

55
112) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions)?
H2, Pd/C

A) A peak around 3300 cm–1 would disappear and nothing new would appear.
B) A peak around 1710 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
C) A peak around 1650 cm–1 would disappear and nothing new would appear.
D) No change would be observed.
E) None of these choices.

Answer: C

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

113) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant overall change(s) would be expected by IR (ignoring C-H absorptions)?
1. Br2, light

2. Zn, HCl

A) A peak around 3300 cm–1 would disappear and nothing new would appear.
B) A peak around 1710 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
C) A peak around 1650 cm–1 would disappear and nothing new would appear.
D) No overall change would be observed.
E) None of these choices.

Answer: D

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

56
114) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions)?
CN a. DiBAl-H CHO
b. H3O+

A) A peak around 2250 cm–1 would disappear and nothing new would appear.
B) A peak around 1720 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
C) A peak around 2250 cm–1 would disappear and a new peak around 1720 cm–1 would appear.
D) A peak around 2250 cm–1 would disappear and a new peak around 3300 cm–1 would appear.
E) No change would be observed.

Answer: C

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

115) The IR stretching frequency occurs at the lowest frequency for which of these bonds?

A) C–H
B) C–O
C) C–Br
D) C–N
E) C–F

Answer: C

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

116) The IR stretching frequency can be predicted to occur at the highest frequency for which of
these bonds?

A) C–H
B) C–F
C) C–Cl
D) C–Br
E) C–I

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

57
117) The IR absorption due to the stretching of which of these carbon-hydrogen bonds occurs at
the highest frequency?

A) I
B) II
C) III
D) IV
E) V

Answer: E

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

118) An oxygen-containing compound which shows sharp IR absorption at 2200 cm-1 and 3300
cm-1 is likely to contain which functional group?

A) An ester
B) An alkene
C) An alkyne
D) An ether
E) An aldehyde

Answer: C

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

58
119) n-Pentane has a higher boiling point than isopentane due to an increased surface-to-surface
interaction of dispersion forces.

A) True
B) False

Answer: A

Topic: Intermolecular Forces

Section Reference 1: 2.13
Difficulty: Easy

120) Carbon dioxide has a higher boiling point than carbon disulfide due to its dipole-dipole
forces.

A) True
B) False

Answer: B

Topic: Intermolecular Forces

Section 2.13
Difficulty: Medium

121) Even though methyl amine (CH3NH2) has a higher molecular weight than water (H2O) , its
boiling point is much lower than water’s boiling point since water has hydrogen bonding
attractive forces.

A) True
B) False

Answer: B

Topic: Intermolecular Forces

Section Reference 1: 2.13
Difficulty: Hard

59
122) Hydrogen bonding will broaden the O–H absorption band in an infrared spectrum.

A) True
B) False

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy

123) The higher the wave number in the infrared spectra, the greater the energy that is required
to vibrate the bond.

A) True
B) False

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

124) The molecule N2 does not show an absorption in an IR spectrum because the dipole moment
of the molecule does not change with the absorption of IR energy.

A) True
B) False

Answer: A

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

125) Hydrocarbons containing carbon-carbon double bonds are referred to as ___.

Answer: alkenes

Topic: Functional Groups

Section Reference 1: 2.1
Difficulty: Easy

60
126) All of the carbon-carbon bonds in ___ are equal to one and one-half bonds and have a bond
length in between that of a single bond and a double bond with all of the bond angles at ___.

Answer: benzene, 120o

Topic: Functional Groups

Section Reference 1: 2.1
Difficulty: Easy

127) Unsaturated hydrocarbons may be distinguished from saturated hydrocarbons by the

presence of one or more ___.

Answer: pi bonds

Topic: Functional Groups

Section Reference 1: 2.1
Difficulty: Easy

128) Draw a structural formula for C8H18, in which there are two quaternary carbons.

Answer:

Topic: Isomers, Functional Groups

Section Reference 1: 2.1
Difficulty: Easy

129) The six p electrons in benzene are ___ about the ring, which explains why all of the C-C
bonds are the same length.

Answer: delocalized

Topic: General
Section Reference 1: 2.1
Difficulty: Easy

61
130) Draw all isomers of C6H14.

Answer:

Topic: Isomers, Functional Groups

Section Reference 1: 1.3A and 2.1
Difficulty: Easy

131) A polar covalent bond is one in which electrons are ___.

Answer: not shared equally

Topic: General
Section Reference 1: 2.2
Difficulty: Easy

132) The ___ is defined as the product of the magnitude of the charge of a particle and the
distance that separates them.

Answer: dipole moment

Topic: Polar Covalent Bond

Section Reference 1: 2.2
Difficulty: Easy

133) Carbon dioxide is non-polar, despite the fact that oxygen is much more electronegative than
carbon. Briefly explain why, using relevant diagrams as appropriate to illustrate your answer.

Answer: The overall dipole moment of a polyatomic molecule depends on two factors: the
polarity of various bonds and molecular geometry, since dipole forces have both magnitude and
direction. In some molecules containing bonds of identical polarity, the molecular geometry may
result in a net cancellation of the overall dipole forces. This is what happens in carbon dioxide:
although there are two polar C-O bonds, because of the linear geometry of the molecule, the net
dipole is zero.

Topic: Molecular Geometry, Dipole Moment

Section Reference 1: 2.2 and 2.3
Difficulty: Medium

62
134) Nitromethane is a polar molecule but contains 2 equal polar covalent bonds. Briefly explain
why and draw a relevant 3-dimensional structure to show the overall dipole moment of the
molecule.

Answer: The nitro group has 2 polar N-O bonds that are pointing 120o apart which do not
completely cancel out and the C-N bond is polar as well which further adds to the net direction
of the dipole.

Topic: Molecular Geometry, Dipole Moment

Section Reference 1: 2.2 and 2.3
Difficulty: Medium

135) Organic compounds are classified into chemical families on the basis of similarities in
chemical properties; these similarities are primarily due to the presence of characteristic
arrangements of atoms known as ___.

Answer: functional groups

Topic: Functional Groups

Section Reference 1: 2.4
Difficulty: Easy

136) Draw all isomers of C3H8O and classify each according to functional group.

Answer:

Topic: Isomers, Functional Groups

Section Reference 1: 1.3, 2.6, and 2.7
Difficulty: Easy

63
137) Draw all tertiary amine isomers of C6H15N.

Answer:

Topic: Isomers, Functional Groups

Section Reference 1: 1.3 and 2.8
Difficulty: Medium

138) Draw all of the acyclic secondary amines that have the chemical formula C4H9N.

Answer:

Topic: Isomers, Functional Groups

Section Reference 1: 1.3 and 2.8
Difficulty: Medium

139) A group in which a carbon atom has a double bond to an oxygen atom is called a ___.

Answer: carbonyl

Topic: Functional Groups

Section Reference 1: 2.9
Difficulty: Easy

64
140) Draw all isomers of C6H12O that are aldehydes and contain at least one tertiary carbon.

Answer:

Topic: Isomers, Functional Groups

Section Reference 1: 2.9
Difficulty: Easy

141) Draw all isomers of C6H12O that are aldehydes.

Answer:

Topic: Isomers, Functional Groups

Section Reference 1: 1.3 and 2.9
Difficulty: Easy

142) Draw all isomers of C5H10O that are ketones.

Answer:

Topic: Isomers, Functional Groups

Section Reference 1: 1.3 and 2.9
Difficulty: Easy

65
143) Draw all of the isomers of C5H9N that are nitriles.

Answer:

Topic: Isomers, Functional Groups

Section Reference 1: 1.3, 2.11
Difficulty: Easy

Question type: Essay

144) Ethanol, C2H5OH, and propane, C3H8, have approximately the same molar mass, yet ethanol
has a much higher boiling point. Briefly explain why.

Answer: Strong hydrogen bonding between molecules of ethanol leads to elevation in boiling
point. No hydrogen bonding is possible between molecules of propane, resulting in a lower
boiling point compared with ethanol.

Topic: Intermolecular Forces

Section Reference 1: 2.13
Difficulty: Easy

145) Even though methanol (CH3OH) and methylamine (CH3NH2) have similar molecular
weights, methanol has a much higher boiling point of 65 oC as opposed to methylamine’s boiling
point of -6 oC. Briefly explain why.

Answer: Both compounds have the same strong intermolecular forces of hydrogen bonding, but
methanol’s O-H bond is much more polarized than methylamine’s N-H as oxygen is more
electronegative than nitrogen. The greater polarization exposes the hydrogen nucleus further and
creates stronger hydrogen bonds.

Topic: Intermolecular Forces

Section Reference 1: 2.13
Difficulty: Easy

66
146) Ethanol, C2H5OH, and dimethyl ether, CH3OCH3, have the same molar mass, yet ethanol
has a much higher boiling point. Briefly explain why.

Answer: Strong hydrogen bonding between molecules of ethanol leads to elevation in boiling
point. No hydrogen bonding is possible between molecules of dimethyl ether, resulting in a
lower boiling point compared with ethanol.

Topic: Intermolecular Forces

Section Reference 1: 2.13
Difficulty: Easy

147) Sodium chloride, which is quite soluble in water, is not very soluble in hexane. Why?

Answer: Sodium chloride, which is an ionic substance, is soluble in a polar solvent such as
water, but not in a non-polar solvent such as hexane.

Topic: Bonding, Solubility

Section Reference 1: 2.13
Difficulty: Medium

148) Explain why the compound shown is considered to be capable of being a soap (dissolving
oily substances off of surfaces using water).

Answer: The compound contains a long hydrophobic “fatty” carbon tail, which attracts grease
particles as they have similar dispersion forces. The polar hydrophilic carboxylate head is forced
to the outside, which the polar water can now dissolve.

Topic: Bonding, Solubility

Section Reference 1: 2.13
Difficulty: Medium

149) Examine the following IR spectrum, for substance Q (C7H14O2). Which oxygen containing

67
functional group is most likely present in Q?

Answer: A carboxylic acid

Topic: Functional Groups, IR Spectroscopy

Section Reference 1: 2.15 and 2.16
Difficulty: Medium

150) Examine the following IR spectrum, for substance P (C3H5NO). Which oxygen containing

68
functional group is most likely present in P?

Answer: Alcohol

Topic: Functional Groups, IR Spectroscopy

Section Reference 1: 2.15 and 2.16
Difficulty: Medium

151) The IR absorption frequencies of the C-H bond in alkanes, alkenes, and alkynes are
measurably different. Briefly explain why.

Answer: IR absorption frequency depends on bond strength; the bond strength of C-H bonds in
alkanes, alkenes and alkynes is different because different atomic orbitals (hybridized) of carbon
are involved in the bond: the C-H bond in alkanes is described as (sp3-s) , that in alkenes is (sp2-
s) and in alkynes, it is (sp-s) . The relative % s v. % p character of the hybrid orbitals of carbon
would indicate different bond lengths / bond strengths for alkanes, alkenes and alkynes, with the
bond length / bond strength being the longest/weakest respectively. This results in different IR
absorption frequencies.

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard

152) IR absorption signals of alcohols are typically broad. However, IR spectra of gaseous

69
samples show sharp peaks. Briefly explain why.

Answer: Broad signals of alcohols are due to hydrogen bonding associated with the O-H group.
In gaseous samples, no hydrogen bonding is possible, and the signal becomes sharp.

Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium

153) An IR spectrum has significant peaks at 3080 and 1650 cm–1. What functional group is
present in the molecule?

Answer: An alkene

Topic: Functional Groups, IR Spectroscopy

Section Reference 1: 2.1, 2.15, and 2.16
Difficulty: Easy

154) An IR spectrum has significant peaks at 2200 and 3300 cm–1. What functional group is
present in the molecule?

Answer: A terminal alkyne

Topic: Functional Groups, IR Spectroscopy

Section Reference 1: 2.1, 2.15, and 2.16
Difficulty: Hard

155) Which is(are) a 2 alkyl halide?

70
A) I
B) II
C) I and III
D) I and IV
E) V

Answer: C

Topic: Functional Groups

Section Reference 1: 2.5
Difficulty: Easy

156) Which is(are) a 1 alkyl halide?

71
A) I
B) II
C) I and III
D) IV and V
E) V

Answer: D

Topic: Functional Groups

Section Reference 1: 2.5
Difficulty: Easy

157) Which compound contains a tertiary alkyl halide?

72
A) I
B) II
C) III
D) IV
E) V

Answer: A

Topic: Functional groups

Section Reference 1: 2.5
Difficulty: Medium

158) Which compound contains a secondary alkyl halide?

A) I
B) II
C) III
D) IV
E) V

Answer: D

Topic: Functional groups

Section Reference 1: 2.5
Difficulty: Medium

159) Which of these compounds is a primary alkyl chloride?

73
A) CH3CH2CH2CH2CH2Cl

B)

C)
D) (CH3)2CHCHClCH3
E) Two of these choices.

Answer: A

Topic: Functional groups

Section Reference 1: 2.5
Difficulty: Medium

160) Which of these compounds is a tertiary alkyl chloride?

A) CH3CH2CH2CH2CH2Cl

B)

C)
D) (CH3)2CHCHClCH3
E) Two of these choices.

Answer: B

Topic: Functional groups

Section Reference 1: 2.5
Difficulty: Medium

161) Which compound listed below is a primary alcohol?

74
A)

B)

C)
D) CH3CH2CH2CH2OH
E) Two of these choices.

Answer: E

Topic: Functional groups

Section Reference 1: 2.6
Difficulty: Easy

162) Which compound listed below is a tertiary alcohol?

A)

B)

C)
D) CH3CH2CH2CH2OH
E) Two of these choices.

Answer: B

Topic: Functional groups

Section Reference 1: 2.6
Difficulty: Easy

163) Which compound is a secondary alcohol?

75
 CH3
OH HO
H3CH2C O
CH3

I II III

O OH

IV V

A) I
B) II
C) III
D) IV
E) V

Answer: B

Topic: Functional groups

Section Reference 1: 2.6
Difficulty: Medium

164) Which compound is an ether?

76
 CH3
OH HO
H3CH2C O
CH3

I II III

O OH

IV V

A) I
B) II
C) III
D) IV
E) V

Answer: D

Topic: Functional groups

Section Reference 1: 2.6
Difficulty: Medium

165) Which compound is a tertiary amine?

77
A) CH3CH2CH2NH2

B)

C)

D)

E)

Answer: D

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

166) Which compound is a primary amine?

A) CH3CH2CH2NH2

B)

C)

D)
E) Two of these choices.

Answer: E

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

167) Which is a 2 amine?

78
A) I
B) II
C) III
D) IV
E) V

Answer: C

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

168) Which is an amide?

79
A) I
B) II
C) III
D) IV
E) V

Answer: E

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

169) An example of a secondary amine is:

80
A) I
B) II
C) III
D) IV
E) V

Answer: B

Topic: Functional groups

Section Reference 1: 2.8
Difficulty: Easy

170) Which compound is an alcohol?

81
A)

B)

C)

D)

E)

Answer: E

Topic: Functional groups

Section Reference 1: 2.9
Difficulty: Easy

171) Which compound is an amide?

82
A) I
B) II
C) III
D) IV
E) V

Answer: A

Topic: Functional groups

Section Reference 1: 2.9
Difficulty: Easy

172) Which compound is a ketone?

83
A) I
B) II
C) III
D) IV
E) V

Answer: B

Topic: Functional groups

Section Reference 1: 2.9
Difficulty: Easy

173) Which compound is an ester?

84
A) I
B) II
C) III
D) IV
E) V

Answer: C

Topic: Functional groups

Section Reference 1: 2.9
Difficulty: Easy

174) Which compound is an alcohol?

85
A) I
B) II
C) III
D) IV
E) V

Answer: E

Topic: Functional groups

Section Reference 1: 2.9
Difficulty: Easy

175) Many organic compounds contain more than one functional group. Which of the following

86
is/are both a ketone and an ether?

A) I
B) II, IV
C) V
D) I, V
E) IV

Answer: E

Topic: Functional Groups

Section Reference 1: 2.7 and 2.9
Difficulty: Easy

176) Which is an ester?

87
A) I
B) II
C) III
D) IV
E) V

Answer: D

Topic: Functional groups

Section Reference 1: 2.10
Difficulty: Easy

177) Which compound is an amide?

88
A) I
B) II
C) III
D) IV
E) V

Answer: A

Topic: Functional groups

Section Reference 1: 2.10
Difficulty: Easy

178) Which compound is an alcohol?

89
A) I
B) II
C) III
D) IV
E) V

Answer: E

Topic: Functional groups

Section Reference 1: 2.10
Difficulty: Easy

179) Which compound can be classified as an ester as well as an aldehyde?

90
A) I
B) II
C) III
D) IV
E) V

Answer: A

Topic: Functional groups

Section Reference 1: 2.9 and 2.10
Difficulty: Medium

180) Which compound would you expect to have the lowest boiling point?

A) n-Butyl alcohol
B) Isobutyl alcohol
C) sec-Butyl alcohol
D) tert-Butyl alcohol
E) Diethyl ether

Answer: E

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

181) Of the following compounds, the one with the lowest boiling point is:

91
A) CH3CH3
B) CH3CH2Cl

C)
D) CH3CH2OH
E) CH3CH2OCH2CH3

Answer: A

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Easy

182) Which compound would you expect to have the lowest boiling point?

A) ethyl alcohol
B) ethyl amine
C) chloroethane
D) water
E) ethane

Answer: E

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

183) Which of these would you expect to have the highest boiling point?

92
A) CH3CH2CH2OH

B)
C) CH3OCH2CH3
D) CH3CH2CH2CH2OH
E) CH3CH2OCH2CH3

Answer: D

Topic: Intermolecular forces

Section Reference 1: 2.13
Difficulty: Medium

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