Deck 19: Amines

Question 1

Provide the IUPAC name for the compound shown below.

Answer 1

3,3-dimethyl-1-butanamine

Question 2

Provide the systematic name for the compound below.

Answer 2

4-aminocyclohexanone

Question 3

Provide the name of the compound shown below.

Answer 3

6-amino-1-methylcyclohexene

Question 4

Draw the structure of N-propyl-4-methyl-3-octanamine.

Question 5

Provide the systematic name for the compound below.
(CH₃)₄N⁺Cl^-

Question 6

Identify the correct systematic name for the following compound.

A) N,N-diethyl-5-hydroxycyclohex-1-enamine
B) N,N-diethyl-4-hydroxycyclohex-1-en-2-amine
C) 3-(diethylamino)cyclohex-3-enol
D) 2-(diethylamino)cyclohex-1-en-4-ol

Question 7

Provide the name of (CH₃CH₂)₄N⁺ Cl^-.

Question 8

Draw the structure of 3-pentanamine.

Question 9

Provide the systematic name for the compound below.

Question 10

Draw the structure of 2,3-dimethyl-2-butanamine

Question 11

Name the compound shown below.

Question 12

Provide the IUPAC name of (CH₃)₃CCH₂CH₂NHCH₂CH₃.

Question 13

Sec-Butylamine is the common name of what compound?

A) 1-butanamine
B) 2-butanamine
C) N-methyl-1-propanamine
D) N-methyl-2-propanamine
E) N-ethylethanamine

Question 14

Provide the structure of N-ethyl-1-butanamine.

Question 15

Name the compound shown below.

Question 16

Draw the structure of piperidine.

Question 17

Draw the structure of N-ethyl-N-methyl-1-hexanamine.

Question 18

Provide the name for the compound below.

Question 19

Which of the following is not an alkaloid?

A) cocaine
B) mesitylene
C) nicotine
D) mescaline
E) morphine

Question 20

Provide the structure of 2,4-dimethylpyridine

Question 21

What common names for 1,4-butanediamine and 1,5-pentanediamine are derived from their characteristic pungent odors?

Question 22

Why can't N-methyl-2-propanamine be resolved into isolable enantiomers even though the compound is chiral?

Question 23

Identify the correct name for the following structure.

A) 5-methyl-4-methylaminocyclohept-5-enol
B) 5-hydroxy-2,N-dimethylcyclohept-2-enamine
C) 4-hydroxy-7,N-dimethylcyclohept-6-enamine
D) 4-methyl-5-methylaminocyclohept-3-enol

Question 24

Which of the following is a secondary amine?

A) cyclohexylamine
B) 3-pentanamine
C) methylamine
D) N,N-dimethylaniline
E) N-ethyl-1-propanamine

Question 25

Provide the correct IUPAC name for the following amine.

A) 4-(methylamino)-2-methyl-1-pentene
B) 2,N-dimethyl-1-penten-4-amine
C) 4,N-dimethyl-4-penten-2-amine
D) 1,3,N-trimethyl-3-buten-1-amine

Question 26

Which of the following compounds is a 2° amine?

A) cyclohexylamine
B) t-butylamine
C) N-ethylaniline
D) N,N-diethylaniline
E) N-butylpyridinium bromide

Question 27

Arrange the following compounds in order of increasing boiling point:
ethyl methyl ether, 1-propanol, N-methylethanamine, and 1-propanamine.

Question 28

Which of the following amines is most soluble in water?

A) pyrrolidine
B) PhNH₂
C) (CH₃)₃N
D) (CH₃CH₂CH₂)₂NH
E) ethylamine

Question 29

Which of the following amines can be resolved into enantiomers?

A) trimethylamine
B) 3-pentanamine
C) 2-pentanamine
D) dimethylammonium chloride
E) 4-(dimethylamino) pyridine

Question 30

The nitrogen's lone pair in pyrrolidine is best described as occupying what type of orbital?

A) s
B) sp³
C) sp²
D) sp
E) p

Question 31

Name the compound shown below.

Question 32

Arrange the following compounds in order of increasing boiling point:
CH₃NHCH₂CH₃, CH₃OCH₂CH₃, (CH₃)₃N, and CH₃CH₂CH₂OH.

Question 33

Why can 1,2,2-trimethylaziridine be resolved into enantiomers while N-methyl-1-propanamine cannot?

Question 34

Which has the higher boiling point, butan-1-ol or 1-butanamine? Explain briefly.

Question 35

Provide the product of the reaction shown below.

Question 36

Arrange the following in order of increasing basicity:
aniline, p-nitroaniline, p-toluidine, and p-methoxyaniline.

Question 37

Which of the following is a tertiary amine?

A) cyclohexylamine
B) 3-pentanamine
C) methylamine
D) N,N-dimethylaniline
E) N-ethyl-1-propanamine

Question 38

Rank the following compounds in order of increasing boiling point (lowest to highest): triethylamine, cyclohexylamine, di-n-propylamine.

Question 39

Circle all of the following structures that can be resolved into pure enantiomers.

Question 40

The nitrogen atom of trimethylamine is ________ hybridized which is reflected in the CNC bond angle of ________.

A) sp, 180°
B) sp², 120°
C) sp², 108°
D) sp³, 120°
E) sp³, 108°

Question 41

Circle the stronger base in the pair below, and briefly explain your choice.

Question 42

A sample of cyclohexylamine is contaminated with considerable hydrocarbon impurity. How might the sample be purified using a technique based on solubility differences?

Question 43

Which of the following amines is most basic?

A) aniline
B) N-ethylaniline
C) N,N-diethylaniline
D) piperidine
E) pyrrole

Question 44

In the mass spectrum of dipropylamine, the base peak appears at m/z ________.

A) 101
B) 86
C) 72
D) 58
E) none of the above

Question 45

Which of the following amines is the strongest base?

A) cyclohexylamine
B) pyrrole
C) p-iodoaniline
D) piperidine
E) imidazole

Question 46

If ethanol has a pK_a value of 16, what is the pK_b value of the ethoxide anion?

Question 47

How might one distinguish a sample of n-butylamine from a sample of diethylamine using IR spectroscopy?

Question 48

Circle the stronger base in the pair below, and briefly explain your choice.

Question 49

When pentanal reacts with ethylamine under conditions of acid catalysis, the major organic product is ________.

A) a ketone
B) a nitrile
C) an imine
D) an oxime
E) a hydrazone

Question 50

How might one distinguish a sample of trimethylamine from a sample of n-propylamine using IR spectroscopy?

Question 51

Circle the stronger base in the pair below, and briefly explain your choice.

Question 52

In ¹H NMR protons on the α-carbon of amines typically absorb between θ:

A) 1.0 and 2.0 ppm.
B) 2.0 and 3.0 ppm.
C) 3.0 and 4.0 ppm.
D) 6.0 and 7.0 ppm.
E) 9.0 and 10.0 ppm.

Question 53

A three-carbon, nitrogen-containing compound exhibits 3 ¹³C NMR peaks (d 11.2, 27.3, and 44.9). Which of the following compounds best matches this spectral data?

A) H₂NCH₂CH₂CH₂OH
B) (CH₃)₂CHNH₂
C) CH₃NHCH₂CH₃
D) CH₃CH₂CH₂NH₂
E) CH₃CH₂C≡N

Question 54

Provide the structure of the major organic product in the reaction below.

Question 55

The following structure has been used in monitoring the development of amyloid plaques in Alzheimer's patients (J. Med. Chem. $\textbf{ 2011, }$ 949). Which sequence correctly ranks the following nitrogens in order of increasing pK_b value?

A) 2 < 3 < 1
B) 3 < 2 < 1
C) 2 < 1 < 3
D) 1 < 3 < 2

Question 56

Since alkyl groups are electron donors, one might conclude that tertiary amines are much more basic than primary amines. Actually, primary and tertiary amines show similar ranges of basicity. Offer an explanation.

Question 57

When CH₃CH₂CHO reacts with PhNHNH₂ under conditions of acid catalysis, the major organic product is ________.

A) a ketone
B) a nitrile
C) an imine
D) an oxime
E) a hydrazone

Question 58

The α-carbon atom bonded to the nitrogen of an alkylamine usually appears in what chemical shift (δ) range?

A) 5-20
B) 30-50
C) 80-100
D) 120-150
E) 180-220

Question 59

How might the presence of an N-H functionally be indicated using NMR spectroscopy?

Question 60

Physostigmine is used in the treatment of glaucoma. Within this structure, the atom indicated by ________ is most basic, while atom ________ is least basic.

A) 1 (most basic), 4 (least basic)
B) 1 (most basic), 3 (least basic)
C) 2 (most basic), 4 (least basic)
D) 2 (most basic), 3 (least basic)
E) None of the above

Question 61

Provide the structure of the major organic product in the reaction below.

Question 62

Provide the major organic compound in the following reaction.

Question 63

Which compound would react most rapidly with sodium methoxide and heat?

A) chlorobenzene
B) 2-chloropyridine
C) 3-chloropyridine
D) 3-chloropyrrole

Question 64

What reagent is needed to accomplish the transformation below?

Question 65

Provide the major organic product of the following reaction.

Question 66

Complete the following reaction by filling in the necessary reagents.

Question 67

Which of the following is an intermediate in the mechanism for amide synthesis through acylation of an amine?

A)

B)

C)

D)

Question 68

Pyridine does not undergo Friedel-Crafts reactions. Offer an explanation.

Question 69

When pyrrole undergoes electrophilic aromatic substitution, at which position does substitution occur?

A) 2-position
B) 3-position
C) 4-position

Question 70

Provide the major organic product of the following reaction.

Question 71

Provide the structure of the major organic product in the reaction below.

Question 72

Provide the structure of the major organic product in the reaction below.

Question 73

Devise an efficient method for preparing p-nitrobenzoic acid from toluene.

Question 74

When pyridine is treated with a mixture of nitric and sulfuric acids, the major product is:

A) 2-nitropyridine.
B) 3-nitropyridine.
C) 4-nitropyridine.
D) 3-aminopyridine.
E) 4-aminopyridine.

Question 75

Why are strongly acidic reagents inappropriate when attempting an electrophilic aromatic substitution with aniline?

Question 76

Which of the following chloropyridines readily undergo nucleophilic substitution upon treatment with NaCN?

A) 2-chloropyridine
B) 3-chloropyridine
C) 4-chloropyridine
D) both A and C
E) both A and B

Question 77

Can 2-methyl-2-butanamine be prepared in good yield from the reaction of ammonia with 2-bromo-2-methylbutane? Why or why not?

Question 78

Pyridine typically undergoes electrophilic aromatic substitution ________ rapidly than benzene, and its preferred site of substitution is the ________ - position.

A) more, 2
B) more, 3
C) more, 4
D) less, 2
E) less, 3

Question 79

Can 1-hexanamine be prepared in good yield from the reaction of a 1:1 molar ratio of ammonia and 1-bromohexane? Why or why not?

Question 80

What compound results from the reaction below?

A) imine
B) amide
C) primary amine
D) quaternary ammonium salt
E) nitrous acid