Smith6e Chapter23 TB AnswerKey

Organic Chemistry, 6e (Smith)
Chapter 23 Amines
1) Which of the following amines are classified as primary (1°) amines?
A) I
B) II
C) III
D) I and II
Answer: D
Difficulty: 1 Easy
Section: 23.01
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
2) Which of the following amines are classified as secondary (2°) amines?
A) I
B) II
C) III
D) I and II
Answer: C
Difficulty: 1 Easy
Section: 23.01
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
1
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3) Which of the following amines are classified as tertiary (3°) amines?
A) I
B) II
C) III
D) IV
Answer: B
Difficulty: 1 Easy
Section: 23.01
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
4) What is the approximate bond angle of the substituents around a nitrogen atom in amines?
A) 90°
B) 109.5°
C) 120°
D) 180°
Answer: B
Difficulty: 1 Easy
Section: 23.02
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
Accessibility: Keyboard Navigation
2
5) Although an amine nitrogen atom containing an electron pair and bonded to three different
groups is technically a stereogenic center, the chirality of the amine nitrogen is often ignored.
Why is that?
A) Because four bonds are needed to define a stereogenic center
B) Because chirality only exists with the tetrahedral carbon atoms
C) Because there is usually slow interconversion between the two isomeric forms at room
temperature
D) Because there is usually rapid interconversion between the two isomeric forms at room
temperature
Answer: D
Difficulty: 1 Easy
Section: 23.04
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
6) Why should the chirality of an ammonium salt with four different groups on the nitrogen atom
not be ignored?
A) Because there is rapid interconversion between the two isomeric forms at room temperature
B) Because interconversion cannot occur between the two isomeric forms at room temperature
C) Because the compound would be a meso compound
D) Because the compound would be a racemic mixture
Answer: B
Difficulty: 1 Easy
Section: 23.04
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
3
7) What is the common name of the following compound?
A) Isopropylamine
B) Sec-butylamine
C) 2-Methyl-1-propanamine
D) Isobutylamine
Answer: D
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
A) isopropylamine
B) sec-butylamine
C) isobutylamine
D) tert-butylamine
Answer: B
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
4
A) isopropylamine
B) 2-methyl-2-propanamine
C) tert-butylamine
D) isobutylamine
Answer: C
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
A) diisopropylamine
B) dipropylamine
C) diisopropanamine
D) dibutylamine
Answer: A
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
5
A) dimethylisobutylamine
B) butyldimethylamine
C) N,N-dimethylbutanamine
D) sec-butyldimethylamine
Answer: D
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
12) What is the IUPAC name of the following compound?
A) N-propylhexanamine
B) N-propylaniline
C) N-ethylcyclohexylamine
D) N-propylcyclohexanamine
Answer: D
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
6
A) N-ethyl-N-methylpentylamine
B) N-ethyl-N-methyl-1-pentanamine
C) N-methyl-3-octanamine
D) N-ethyl-2-heptanamine
Answer: B
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
A) 3-methyl-1-hexanamine
B) 4-methyl-1-hexylamine
C) 4-methyl-1-hexanamine
D) 3-methyl-6-hexylamine
Answer: C
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
7
A) N-ethyl-N-methylcyclopentanamine
B) N-cyclopentyl-N-methylethanamine
C) N-methyl-N-ethylcyclopentylamine
D) N-ethyl-N-methylpentanamine
Answer: A
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
A) 1-methyl-N-propyl-1-propanamine
B) 4-methyl-4-heptanamine
C) 2-propyl-3-hexanamine
D) N-propyl-2-pentanamine
Answer: D
Difficulty: 1 Easy
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
8
A) (S)-methyl-4-hexanamine
B) (S)-5-methyl-3-hexanamine
C) (R)-2-methyl-4-hexanamine
D) (R)-5-methyl-3-hexanamine
Answer: B
Difficulty: 2 Medium
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
A) (Z)-4-hexen-1-amine
B) (E)-4-hexen-1-amine
C) (E)-2-hexen-6-amine
D) (Z)-2-hexen-6-amine
Answer: B
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
9
19) What is the correct assignment of the names of the following aromatic amines?
A) I = pyrrolidine; II = pyrimidine; III = aniline

B) I = pyrrole; II = pyrimidine; III = anisole
C) I = pyrrolidine; II = pyridine; III =aniline
D) I = pyrrole; II = pyridine; III = aniline
Answer: D
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
20) Arrange the following compounds in order of decreasing boiling point, putting the compound
with the highest boiling point first.
A) I > II > III

B) I > III > II
C) III > I > II
D) III > II > I
Answer: C
Difficulty: 1 Easy
Section: 23.04
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
10
21) Arrange the following compounds in order of increasing boiling point, putting the compound
with the least boiling point first.
A) I < II < III

B) II < I < III
C) I < III < II
D) II < III < I
Answer: D
Difficulty: 1 Easy
Section: 23.04
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
22) Arrange the following amines in order of decreasing water solubility, putting the most
soluble amine first.
A) I > II > III

B) II > I > III
C) III > I > II
D) II > III > I
Answer: B
Difficulty: 1 Easy
Section: 23.04
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
11
23) The mass spectrum of an amine shows a parent peak with an odd mass for the molecular ion.
What does this tell you about the amine?
A) The amine is a primary amine.
B) The amine is a secondary amine.
C) The amine contains an even number of N atoms.
D) The amine contains an odd number of N atoms.
Answer: D
Difficulty: 1 Easy
Section: 23.04
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
24) What is a typical characteristic absorption in the IR spectrum of a primary amine?

A) Two N-H absorptions at 2500-2600 cm-1
B) One N-H absorption at 2500-2600 cm-1
C) Two N-H absorptions at 3300-3500 cm-1
D) One N-H absorption at 3300-3500 cm-1
Answer: C
Difficulty: 1 Easy
Section: 23.04
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
12
25) A compound with molecular formula C6H15N exhibits a singlet at d 0.9 (1H), a triplet at d
1.10 (3H), a singlet at d1.15 (9H), and a quartet at d 2.6 (2H) in its 1HNMR spectrum. Its IR
spectrum shows one medium absorption band near 3400 cm-1. What is the structure of this
compound?
A) I
B) II
C) III
D) IV
Answer: B
Section: 23.04
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
26) What is the name given to naturally occurring amines derived from plant sources?
A) Enamines
B) Imines
C) Alkaloids
D) Alkamines
Answer: C
Difficulty: 1 Easy
Section: 23.05
Topic: Amines
Bloom's: 1. Remember
Chapter: 23
13
27) Why is direct nucleophilic substitution of an alkyl halide with NH3 not a very useful method
for preparing primary amines?
A) NH3 is not a nucleophile.
B) Elimination will occur.
C) NH3 is too bulky to act as a nucleophile.
D) Polyalkylation of the amine will result in multiple products.
Answer: D
Difficulty: 1 Easy
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
28) In the preparation of primary amines, how can direct nucleophilic substitution between NH 3
and alkyl halide be made more practical than reacting NH3 and the alkyl halide in a 1:1 ratio?
A) Use a large excess of NH3.
B) Use a large excess of alkyl halide.
C) Use a limited amount of NH3.
D) Make the alkyl halide sterically hindered.
Answer: A
Difficulty: 1 Easy
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
29) Why is the N-H bond of an imide especially acidic?

A) The conjugate base is stabilized by electron-donating inductive effect.
B) The conjugate base is stabilized by resonance.
C) The conjugate acid is stabilized by resonance.
D) The conjugate base is stabilized by intramolecular hydrogen bonding.
Answer: B
Difficulty: 1 Easy
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
14
30) Which of the following alkyl halides cannot be used to prepare primary amines by the
Gabriel synthesis?
A) 2-Bromo-2-methylbutane
B) 1-Bromo-2-methylbutane
C) 2-Bromo-3-methylbutane
D) 1-Bromo-3-methylbutane
Answer: A
Difficulty: 1 Easy
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
31) Predict the product(s) of the following reaction.
A) I
B) II
C) III
D) None of the choices
Answer: B
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
15
32) What is the major organic product obtained in the following reaction?
A) I
B) II
C) III
D) IV
Answer: D
Difficulty: 1 Easy
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
16
A) I
B) II
C) III
D) IV
Answer: B
Difficulty: 1 Easy
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
17
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
18
A) I
B) II
C) III
D) IV
Answer: B
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
36) Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH3)?
A) Because of the electron-withdrawing inductive effect of the alkyl groups
B) Because of the steric hindrance of the alkyl groups
C) Because of the resonance delocalization of the alkyl groups
D) Because of electron-donating inductive effect of the alkyl groups
Answer: D
Difficulty: 1 Easy
Section: 23.08
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
19
37) Why are alkylamines more basic than arylamines?
A) The lone pair electrons are localized in alkylamines and delocalized in arylamines.
B) The lone pair electrons are delocalized in alkylamines and localized in arylamines.
C) The lone pair electrons are less readily available in alkylamines.
D) The lone pair electrons are more readily available in arylamines.
Answer: A
Difficulty: 1 Easy
Section: 23.08
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
38) Rank the following compounds in order of increasing basicity, putting the least basic
compound first.
A) III < II < IV < I

B) II < III < IV < I
C) I < IV < II < III
D) III < I < II < IV
Answer: A
Section: 23.09
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
20
39) Rank the following compounds in order of decreasing basicity, putting the most basic
compound first.
A) II > I > III > IV

B) I > II > III > IV
C) I > III > II > IV
D) IV > II > III > I
Answer: C
Section: 23.09
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
40) Rank the following compounds in order of increasing basicity, putting the least basic first.
A) II < III < IV < I

B) I < II < III < IV
C) IV < III < II < I
D) II < I < III < IV
Answer: B
Section: 23.09
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
21
41) Rank the following compounds in order of decreasing basicity, putting the most basic first.
A) I > II > III > IV

B) I > III > II > IV
C) IV > III > I > II
D) II > I > III > IV
Answer: D
Section: 23.09
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
42) Why is pyrrole much less basic than pyridine?

A) The lone pair of electrons in pyrrole is located on an sp2 orbital.
B) The lone pair of electrons in pyrrole is part of the aromatic p system.
C) The lone pair of electrons in pyrrole is not part of the aromatic p system.
D) The pKa of the conjugate acid of pyrrole is much greater than the conjugate acid of pyridine.
Answer: B
Difficulty: 1 Easy
Section: 23.09
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
22
43) Why is piperidine a stronger base than pyridine?
A) The lone pair of electrons in pyridine is part of the delocalized p system.
B) Aromatic compounds are always less basic than non-aromatic compounds.
C) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in
pyridine is in an sp hybrid orbital.
D) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in
pyridine is in an sp2 hybrid orbital.
Answer: D
Section: 23.09
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
44) Rank the following compounds in increasing order of basicity, putting the least basic first.
A) II < I < IV < III

B) I < III < II < IV
C) IV < II < III < I
D) I < II < III < IV
Answer: B
Section: 23.09
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
23
45) Rank the nitrogen atoms in chloroquine, shown below, in order of decreasing basicity,
putting the most basic nitrogen atom first.
A) N1 > N2 > N3
B) N2 > N1 > N3
C) N3 > N2 > N1
D) N3 > N1 > N2
Answer: C
Difficulty: 3 Hard
Section: 23.09
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
24
46) Histamine, a vasodilator, is responsible for a wide variety of physiological effects. Rank the
three nitrogen atoms in histamine in increasing order of basicity, putting least basic nitrogen
atom first.
A) N2 < N1 < N3
B) N1 < N2 < N3
C) N3 < N1 < N2
D) N3 < N2 < N1
Answer: A
Difficulty: 3 Hard
Section: 23.08
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
25
47) Predict the major organic product of the following reaction.
A) I
B) II
C) III
D) IV
Answer: B
Difficulty: 1 Easy
Section: 23.11
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
A) I
B) II
C) III
D) IV
Answer: D
Difficulty: 1 Easy
Section: 23.11
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
26
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: 23.11
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
27
A) I
B) II
C) III
D) IV
Answer: D
Difficulty: 1 Easy
Section: 23.12
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
51) Predict the major product of the following reaction.
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: 23.12
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
28
A) I
B) II
C) III
D) IV
Answer: B
Difficulty: 1 Easy
Section: 23.12
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
53) Select the reagent(s) required for the following transformation.
A) NaI
B) (1) NaNO2, HCl; (2) NaI
C) (1) NaNO2, HCl; (2) I2
D) I2
Answer: B
Difficulty: 1 Easy
Section: 23.07
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
29
A) NaF
B) (1) NaNO2, HCl; (2) F2
C) (1) NaNO2, HCl; (2) HBF4
D) F2
Answer: C
Difficulty: 1 Easy
Section: 23.07
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
A) (1) NaNO2, HCl; (2) H2

B) (1) NaNO2, HCl; (2) H2O
C) (1) NaNO2, HCl; (2) H3PO4
D) (1) NaNO2, HCl; (2) H3PO2
Answer: D
Difficulty: 1 Easy
Section: 23.12
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
30
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: 23.12
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
31
A) I
B) II
C) III
D) IV
Answer: D
Difficulty: 1 Easy
Section: 23.13
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
32
58) What starting materials are required to synthesize the following azo compound?
A) I
B) II
C) III
D) IV
Answer: B
Section: 23.13
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
33
59) Consider the following multistep synthesis.
What is the structure of intermediate A?
A) I
B) II
C) III
D) IV
Answer: B
Section: 23.07
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
34
What is the structure of intermediate B?
A) I
B) II
C) III
D) IV
Answer: D
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
35
What is the structure of intermediate C?
A) I
B) II
C) III
D) IV
Answer: A
Section: 23.07
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
36
62) What is the IUPAC name for the following compound?
A) (E,R)-4-chloro-3-penten-2-amine
B) (E,S)-4-chloro-3-penten-2-amine
C) (Z,R)-4-chloro-3-penten-2-amine
D) (Z,S)-4-chloro-3-penten-2-amine
Answer: C
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
63) What is the IUPAC name for the following compound?
A) (E,R)-4-chloro-3-penten-2-amine
B) (E,S)-4-chloro-3-penten-2-amine
C) (Z,R)-4-chloro-3-penten-2-amine
D) (Z,S)-4-chloro-3-penten-2-amine
Answer: B
Section: 23.03
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
37
64) What is the major product of the following reaction?
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
38
65) What is the major product of the following reaction?
A) I
B) II
C) III
D) IV
Answer: D
Difficulty: 1 Easy
Section: 23.06
Topic: Amines
Bloom's: 3. Apply
Chapter: 23
39

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Smith6e Chapter23 TB AnswerKey

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Organic Chemistry, 6e (Smith)

1) Which of the following amines are classified as primary (1°) amines?

2) Which of the following amines are classified as secondary (2°) amines?

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

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

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

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

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

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

A) I = pyrrolidine; II = pyrimidine; III = aniline

A) I > II > III

A) I < II < III

A) I > II > III

24) What is a typical characteristic absorption in the IR spectrum of a primary amine?

29) Why is the N-H bond of an imide especially acidic?

31) Predict the product(s) of the following reaction.

A) III < II < IV < I

A) II > I > III > IV

A) II < III < IV < I

A) I > II > III > IV

42) Why is pyrrole much less basic than pyridine?

A) II < I < IV < III

48) Predict the major organic product of the following reaction.

51) Predict the major product of the following reaction.

53) Select the reagent(s) required for the following transformation.

55) Select the reagent(s) required for the following transformation.

A) (1) NaNO2, HCl; (2) H2

What is the structure of intermediate A?

What is the structure of intermediate B?

What is the structure of intermediate C?

63) What is the IUPAC name for the following compound?

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