Deck 23: Amines

Question 1

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

Answer 1

(3R,4S)-3-amino-4-methylcyclohexene

Question 2

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 ^$\circ$ amine; 2 = oxime; 3 = hydrazine
D)1 = imine; 2 = hydrazone; 3 = 2 ^$\circ$ amine

Answer 2

1 = imine; 2 = oxime; 3 = hydrazone

Question 3

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

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

Answer 3

2

Question 4

What is the hybridization of the nitrogen atom of pyridine?

A)s
B)sp
C)sp²
D)sp³

Question 5

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

A)1 = 2 ^$\circ$ amine; 2 = enamine; 3 = hydrazine
B)1 = 2 ^$\circ$ amine; 2 = amide; 3 = nitrile
C)1 =oxime; 2 = hydrazone; 3 = nitrile
D)1 = imine; 2 = hydrazone; 3 = amide

Question 6

Which of the following compounds are primary (1 ^$\circ$ ) amines?

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

Question 7

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

A)-2
B)5
C)10
D)25

Question 8

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

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

Question 9

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 10

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

Question 11

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 12

Which of the following is the strongest base?

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

Question 13

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 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 compounds are secondary (2 ^$\circ$ ) amines?
1)(CH₃)₃CNHCH₃
2)CH₃CH(NH₂)CH₂CH₃
3)CH₃CH₂CH₂NHCH₃
4)CH₃CH₂CH₂CH₂CH₂NH₂

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

Question 16

Which of the following compounds are tertiary (3 ^$\circ$ ) amines?
1)(CH₃)₂CHN(CH₃)₂
2)CH₃CH(CH₃)N(CH₂CH₃)₂
3)CH₃CH₂CH₂NHCH₃
4)CH₃CH₂CH₂CH₂CH₂NH₂

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

Question 17

Which of the following is the strongest base?

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

Question 18

Which of the following is the weakest base?

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

Question 19

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 ^$\circ$ amine; 2 = amide; 3 = hydrazone
C)1 =oxime; 2 = hydrazone; 3 = nitrile
D)1 = amide; 2 = nitrile; 3 = hydrazone

Question 20

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 21

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

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

Question 22

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

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

Question 23

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

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

Question 24

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

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

Question 25

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

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

Question 26

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

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

Question 27

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

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

Question 28

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

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

Question 29

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

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

Question 30

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

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

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 intermediate in the Hofmann elimination, in which a 1 ^$\circ$ or 2 ^$\circ$ 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 ^$\circ$ carbocation
D)an amine oxide

Question 34

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

A)a tetraalkylammonium hydroxide salt
B)an amine oxide
C)a 3 ^$\circ$ carbocation
D)an amide anion

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 reaction?

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

Question 38

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

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

Question 39

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

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

Question 40

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

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

Question 41

The compound circled below represents a heterocyclic amine.

Question 42

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 43

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

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

Question 44

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

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

Question 45

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

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

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

Question 48

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 49

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 50

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 51

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 52

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

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

Question 53

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 54

The pK_a of methyl amine is represented by the following reaction.

Question 55

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

Question 56

The following structure is classified as a 3° amine.

Question 57

Consider the following reaction.

The products of this reaction are shown below.

Question 58

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

Question 59

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 60

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 61

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 62

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

Question 63

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

Question 64

What is the IUPAC name of the following compound?

Question 65

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

Question 66

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

Question 67

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

Question 68

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

Question 69

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

Question 70

What is the IUPAC name of the following compound?

Question 71

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

Question 72

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

Question 73

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 74

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

Question 75

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

Question 76

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 77

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

Question 78

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 79

Provide a line-bond structure of N-methylaniline.

Question 80

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