Deck 23: Amines

Question 1

Which of the following is the strongest base?

A) phenol
B) aniline
C) methylamine
D) 4-nitroaniline

Answer 1

methylamine

Question 2

What is the correct assignment of the names of the functional groups in the following nitrogen-containing compounds?

A) 1 = 2° amine; 2 = enamine; 3 = hydrazine
B) 1 = 2° amine; 2 = amide; 3 = nitrile
C) 1 =oxime; 2 = hydrazone; 3 = nitrile
D) 1 = imine; 2 = hydrazone; 3 = amide

Answer 2

1 = 2° amine; 2 = enamine; 3 = hydrazine

Question 3

What is the hybridization of the nitrogen atoms labeled i and ii in the aromatic imidazole ring?

A) i = sp^2;; ii = sp²
B) i = sp²; ii = sp³
C) i = sp³; ii = sp³
D) i = sp³; ii = sp²

Answer 3

i = sp^2;; ii = sp²

Question 4

What is the correct assignment of the names of the functional groups in the following nitrogen-containing compounds?

A) 1 = imine; 2 = hydrazone; 3 = amide
B) 1 = 2° amine; 2 = amide; 3 = hydrazone
C) 1 =oxime; 2 = hydrazone; 3 = nitrile
D) 1 = amide; 2 = nitrile; 3 = hydrazone

Question 5

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 6

Which of the following is the weakest base?

A) aniline
B) 3-nitroaniline
C) 4-nitroaniline
D) 4-methoxyaniline

Question 7

Which of the following will remove aniline from a solution of aniline in diethyl ether?

A) aqueous KBr
B) aqueous HCl
C) aqueous NaOH
D) aqueous CH₃COONa

Question 8

What is the IUPAC name of the following compound?

A) (3R,4S)-3-amino-4-methylcyclohexene
B) (3R,4R)-3-amino-4-methylcyclohexene
C) (4R,5S)-5-amino-4-methylcyclohexene
D) (4R,5R)-5-amino-4-methylcyclohexene

Question 9

What is the approximate pK_a value of (CH₃)₃NH⁺, the conjugate acid of trimethylamine?

A) −2
B) 5
C) 10
D) 25

Question 10

What is the correct assignment of the names of the functional groups in the following nitrogen-containing compounds?

A) 1 = amide; 2 = 2 amine; 3 = oxime
B) 1 = imine; 2 = oxime; 3 = hydrazone
C) 1 = 2° amine; 2 = oxime; 3 = hydrazine
D) 1 = imine; 2 = hydrazone; 3 = 2° amine

Question 11

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 12

What is the IUPAC name of the following compound?

A) 1-aminobicyclo[2.2.2]octane
B) 2-aminobicyclo[2.2.2]octane
C) 4-aminobicyclo[2.2.2]octane
D) 2-aminobicyclo[6.4.4]octane

Question 13

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 14

Which of the following is the weakest base?

A) 4-methylaniline
B) 4-nitroaniline
C) aniline
D) 4-chloroaniline

Question 15

Which of the following is the strongest base?

A) ammonia
B) dimethylamine
C) aniline
D) 4-nitroaniline

Question 16

What is the hybridization of the nitrogen atom of pyridine?

A) s
B) sp
C) sp²
D) sp³

Question 17

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 18

What is the IUPAC name of the following compound?

A) (E)-1-amino-4-hexene
B) (E)-6-amino-2-hexene
C) 3-allyl 1-aminopropane
D) (Z)-1-amino-2-hexene

Question 19

What is the IUPAC name of the following compound?

A) (R)-4-amino-2-methylhexane
B) (S)-4-amino-2-methylhexane
C) N-ethyl N-(3-methylpropyl) amine
D) (R)-3-amino-5-methylhexane

Question 20

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 21

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 22

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 23

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 24

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 25

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 26

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 27

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 28

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 29

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 30

What is the intermediate in the Hofmann elimination, in which a 1° or 2° alkyl halide is treated with trimethyl amine, followed by addition of silver(I) oxide and heat?

A) a tetraalkylammonium hydroxide salt
B) a tertiary amine
C) a 3° carbocation
D) an amine oxide

Question 31

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 32

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 33

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 34

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 35

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 36

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 37

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 38

What is the intermediate in the Cope elimination, in which a 3° amine is treated with hydrogen peroxide followed by heat?

A) a tetraalkylammonium hydroxide salt
B) an amine oxide
C) a 3° carbocation
D) an amide anion

Question 39

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 40

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 41

Consider the following compounds. Answer the following questions by filling in the blank with the appropriate number from the diagram or an appropriate term.
The ammonia ion of substance ____ will have the smallest pK_a.

Question 42

The following structure is classified as a 3° amine.

Question 43

Which combination of carbonyl compound and amine can be used to prepare the following product by reductive amination?

A) only 1
B) only 3
C) only 1 and 3
D) only 2 and 4

Question 44

Which combination of carbonyl compound and amine can be used to prepare the following product by reductive amination?

A) only 1
B) only 3
C) only 1 and 3
D) only 2 and 4

Question 45

Which of the following amines can be prepared by reduction of an amide?

A) tert-butyl amine
B) 2-hexanamine
C) N-methyl-1-butanamine
D) aniline

Question 46

Consider the following compounds. Answer the following questions by filling in the blank with the appropriate number from the diagram or an appropriate term.
The ammonia ion of substance ____ will have the largest pK_a.

Question 47

Consider the following reaction. $+\mathrm{HONO}+\mathrm{HCl} \stackrel{0^{\circ} \mathrm{C}}{\longrightarrow}$ The products of this reaction are shown below. $+\mathrm{H}_{2} \mathrm{O}+\mathrm{HCl}$

Question 48

The following amine can be converted to an aryl diazonium salt.

Question 49

To separate a mixture of p-toluidine and p-nitrotoluene dissolved in ether,extract the ether solution with aqueous HCl and treat the water layer with aqueous NaOH.

Question 50

Which of the following amines can be prepared from an organic bromide by reaction with sodium azide followed by reduction?

A) aniline
B) benzylamine
C) N-ethyl-2-butanamine
D) tert-butyl amine

Question 51

The pK_a of methyl amine is represented by the following reaction. $\mathrm{CH}_{3} \mathrm{NH}_{3}^{+}+\mathrm{H}_{2} \mathrm{O}$$\rightleftharpoons$$\mathrm{CH}_{3} \mathrm{NH}_{3}+\mathrm{H}_{3} \mathrm{O}^{+}$

Question 52

Which of the following amines can be prepared by ring opening of an epoxide with sodium amide followed by reduction?

A) only 1
B) only 1 and 2
C) only 1 and 4
D) 1, 2, 3 and 4

Question 53

The reaction of a 2^o amine with nitrous acid gives a nitrosamine.

Question 54

Which of the following amines can be prepared by treatment of a carbonyl compound with sodium cyanide in the presence of acid, followed by reduction?

A) only 1
B) only 1 and 2
C) only 1, 2 and 3
D) 1, 2, 3 and 4

Question 55

Which of the following amines can be prepared from an organic bromide reaction with potassium cyanide followed by reduction?

A) 1-heptanamine
B) benzylamine
C) 2-butanamine
D) tert-butyl amine

Question 56

The following represents an acid-base reaction between the given amine and HCl.

Question 57

Aliphatic 3^o amines with three different groups on nitrogen can be resolved.

Question 58

Consider the following compounds. Answer the following questions by filling in the blank with the appropriate number from the diagram or an appropriate term.
Substance _____ is a primary alkyl amine.

Question 59

The name of the product formed by reacting CuCl and HCl with benzenediazonium chloride is ________________________.

Question 60

The compound circled below represents a heterocyclic amine.

Question 61

What is the major organic product obtained from the following sequence of reactions?

Question 62

Provide a brief explanation, based on features of the molecules, for the following trend in pK_a values?
​ ​
4.15 4.63 1.0

Question 63

What is the major organic product obtained form the following sequence of reactions?

Question 64

Provide a line-bond structure of N-methylaniline.

Question 65

Provide a line-bond structure of N,N-dimethylcyclopentanamine.

Question 66

What is the major organic product obtained from the following sequence of reactions?

Question 67

What is the major organic product obtained from the following sequence of reactions?

Question 68

What is the major organic product obtained form the following sequence of reactions?

Question 69

What is the IUPAC name of the following compound?

Question 70

What is the major organic product obtained from the following sequence of reactions?

Question 71

What is the major organic product obtained from the following sequence of reactions?

Question 72

The name of the product formed by reacting KCN and CuCN with benzenediazonium chloride is ________________________.

Question 73

What is the major organic product obtained from the following sequence of reactions?

Question 74

Consider the following substances. Complete the following statements using the appropriate number.
Substance _____ is aniline.

Question 75

What is the major organic product obtained from the following reaction?

Question 76

Provide a brief explanation, based on features of the molecules, for the following difference in pK_a values?
CH₃NH₂ > PhNH₂
10.64 4.63

Question 77

Provide a brief explanation, based on features of the molecules, for the following difference in pK_a values?
​
CH₃NH₂ > NH₃
10.64 9.26

Question 78

What is the IUPAC name of the following compound?

Question 79

Consider the following substances. Complete the following statements using the appropriate number.
Substance _____ is pyridine.

Question 80

Consider the following substances. Complete the following statements using the appropriate number.
Substance _____ is pyrrole.