Deck 19: Amines

Question 1

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

Answer 1

CH₃CH₂CH₂CH₂NHCH₂CH₃

Question 2

Name the compound shown below.

Answer 2

N,N-dimethyl-3-pentanamine or N,N-dimethylpentan-3-amine

Question 3

Provide the name of the compound shown below.

Answer 3

6-amino-1-methylcyclohexene

Question 4

Provide the name of (CH₃CH₂)₄N⁺ Cl^-.

Question 5

Provide the systematic name for the compound below.

Question 6

Name the compound shown below.

Question 7

Provide the IUPAC name for the compound shown below.

Question 8

Provide the structure of 2,4-dimethylpyridine.

Question 9

Draw the structure of piperidine.

Question 10

Draw the structure of 3-pentanamine.

Question 11

The structure of morphine is shown below. The amine in morphine is classified as ________.

A) 1°
B) 2°
C) 3°
D) aryl

Question 12

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

Question 13

Provide the systematic name for the compound below.

Question 14

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 15

Provide the name for the compound below.

Question 16

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

Question 17

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

Question 18

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 19

Provide the IUPAC name of (CH₃)₃CCH₂CH₂NHCH₂CH₃.

Question 20

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

Question 21

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

Question 22

Which of the following compounds contains a tertiary amine?
1) 2-methyl-2-propanamine
2) N-ethylpyrrolidine
3) N-methylcyclohexylamine
4) 2-(dimethylamino)butanal

Question 23

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 24

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 25

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 26

Identify the correct name for the following structure.

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

Question 27

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

Question 28

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

Question 29

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 30

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

Question 31

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

Question 32

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

Question 33

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

Question 34

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 35

Provide the product of the reaction shown below.

Question 36

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

Question 37

Name the compound shown below.

Question 38

Which of the following amines is most soluble in water?

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

Question 39

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 40

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 41

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 42

When aniline is treated with molecular bromine in the presence of a mild base (NaHCO₃), polyhalogenation occurs. However, when aniline is treated with molecular bromine in the presence of a strong Lewis Acid like FeBr₃, no reaction takes place. Briefly explain this difference in reactivity.

Question 43

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

Question 44

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

Question 45

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 46

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

Question 47

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

Question 48

In the mass spectrum of compounds with one nitrogen ________.

A) most fragments are odd and the molecular ion is even
B) most fragments are odd and the molecular ion is odd
C) most fragments are even and the molecular ion is even
D) most fragments are even and the molecular ion is odd

Question 49

Which of the following amines is most basic?

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

Question 50

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 51

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 52

Predict the product of the reaction shown below and add arrows to show the mechanism.

Question 53

In ¹H NMR protons on the α-carbon of amines typically appear in the range of ________.

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 54

Which of the following amines is the strongest base?

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

Question 55

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

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

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 58

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

Question 59

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

Question 60

The following structure has been used in monitoring the development of amyloid plaques in Alzheimer's patients (J. Med. Chem. 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 61

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 62

Complete the following reaction by filling in the necessary reagents.

Question 63

Provide the major organic product of the following reaction.

Question 64

Provide the major organic compound in the following reaction.

Question 65

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

A) 2-position
B) 3-position
C) 4-position
D) At all positions equally

Question 66

What compound results from the reaction below?

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

Question 67

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

Question 68

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

Question 69

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

Question 70

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

Question 71

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

Question 72

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 73

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

A)
B)
C)
D)

Question 74

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

A) pyridine
B) 2-chloropyridine
C) 3-chloropyridine
D) 4-chloropyridine

Question 75

What reagent is needed to accomplish the transformation below?

Question 76

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 77

Predict the major organic product of the following reaction:

Question 78

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 79

Provide the major organic product of the following reaction.

Question 80

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