Deck 22: Amines

Question 1

What is the IUPAC name for the following compound?

A) N-ethylhexanamine
B) N-ethylcyclohexanamine
C) N-cyclohexylethanamine
D) N-ethylcyclopentanamine
E) N-ethylaniline

Answer 1

N-ethylcyclohexanamine

Question 2

What is the common name for the following compound?

A) dibenzylamine
B) diphenylamine
C) dibenzeneamine
D) phenylbenzeneamine
E) none of these

Answer 2

diphenylamine

Question 3

What is the IUPAC name for the following compound?

Answer 3

(1S,2S)-2-methylcyclopentanamine

Question 4

What is the IUPAC name for the following compound?

Question 5

What is the common name for the following compound?

A) ethylmethylisobutylamine
B) diethylisobutylamine
C) sec-butyldiethylamine
D) 2-diethylaminobutane
E) sec-butyldimethylamine

Question 6

What is the common name for the following compound?

A) cyclopentylmethylamine
B) ethylhexylamine
C) cyclohexylethylamine
D) cyclohexylmethylamine
E) ethylhexylmethylamine

Question 7

What is the structure for N,N-diethylaniline?

Question 8

What is the IUPAC name for the following compound?

A) N-cyclopentyl-N-methylcyclohexanamine
B) N-cyclohexyl-N-methylcyclohexanamine
C) N-cyclopentyl-N-methylcyclopentanamine
D) cyclohexylcyclopentylmethylamine
E) N-pentyl-N-methylhexanamine

Question 9

What is the structure for N-ethylbenzylamine?

Question 10

Which of the following is a tertiary amine?

A) CH₃CH₂CH₂CH₂NH₂
B) CH₃CH₂NHCH₂CH(CH₃)₂
C) (CH₃CH₂)₂NCH₂CH(CH₃)₂
D) (CH₃CH₂)₄N⁺ OH^-
E) (CH₃CH₂)₃CNH₂

Question 11

What is the IUPAC name for the following compound?

A) 1-methyl-N-propyl-1-butananmine
B) 4-methyl-5-octanamine
C) 1-ethyl-N-propyl-1-pentanamine
D) N-butyl-2-pentanamine
E) N-methylpropyl-1-butanamine

Question 12

What is the structure for 3-chloro-N-ethyl-1-pentanamine?

Question 13

What is the IUPAC name for the following compound?

A) ethylisobutylisopropylamine
B) ethylisopropylbutylamine
C) sec-butylethylpropylamine
D) sec-butylethylisopropylamine
E) none of these

Question 14

Which of the following is a primary amine?

A) CH₃CH₂CH₂CH₂NH₂
B) CH₃CH₂NHCH₂CH(CH₃)₂
C) (CH₃CH₂)₂NCH₂CH(CH₃)₂
D) (CH₃CH₂)₄N⁺ OH^-
E) (CH₃CH₂)₃N

Question 15

What is the common name for the following compound?

A) N-cyclopentyl-N-methylcyclohexanamine
B) N-cyclohexyl-N-methylcyclohexanamine
C) N-cyclopentyl-N-methylcyclopentanamine
D) cyclohexylcyclopentylmethylamine
E) N-pentyl-N-methylhexanamine

Question 16

Classify the following compounds as a primary, secondary or tertiary amine.

Question 17

Which of the following is a secondary amine?

A) CH₃CH₂CH₂CH₂NH₂
B) CH₃CH₂NHCH₂CH(CH₃)₂
C) (CH₃CH₂)₂NCH₂CH(CH₃)₂
D) (CH₃CH₂)₄N⁺ OH^-
E) (CH₃CH₂)₃CNH₂

Question 18

What is the IUPAC name for the following compound?

A) N,N,1-diethyl-1-ethanamine
B) N,N-diethyl-1-methyl-1-propanamine
C) 2,2-diethyl-2-butanamine
D) N,N-dimethyl-2-butanamine
E) N,N-diethyl-2-butanamine

Question 19

What is the structure for 1-butanamine?

A) CH₃CH₂CH₂CH₂NH₂
B) CH₃CH₂NHCH₂CH(CH₃)₂
C) (CH₃CH₂)₂NCH₂CH(CH₃)₂
D) (CH₃CH₂)₄N⁺ OH^-
E) (CH₃CH₂)₃CNH₂

Question 20

Which of the following is a quaternary ammonium salt?

A) CH₃CH₂CH₂CH₂NH₃⁺ Cl^-
B) (CH₃CH₂)₂NH₂⁺ Cl^-
C) (CH₃CH₂)₃NH⁺ Cl^-
D) (CH₃CH₂)₄N⁺ Cl^-
E) (CH₃CH₂)₂NCH₃

Question 21

What is the IUPAC name for the following compound?

Question 22

Which one of the following is a stronger base? Explain why.

Question 23

Arrange the following compounds in decreasing (strongest to weakest) order of basicity.

A) I > III > II > IV
B) II > III > I > IV
C) IV > III > II > I
D) IV > I > II > III
E) II > I > IV > III

Question 24

Arrange the following compounds in increasing (weakest to strongest) order of basicity.

A) IV < II < I < III
B) III < II < IV < I
C) II < I < III < IV
D) II < III < I < IV
E) None of the above

Question 25

What is the IUPAC name for the following compound?

Question 26

Which of the following compounds is least soluble in water?

A) I
B) II
C) III
D) both I and III
E) none of these

Question 27

What is the IUPAC name for the following compound?

Question 28

Identify the strongest base.

A) 4-chloroaniline
B) 4-nitroaniline
C) 4-aminobenzonitrile
D) aniline
E) 4-aminoanisole

Question 29

Which of the following compounds is most soluble in water?

A) I
B) II
C) III
D) both I and II
E) all of these

Question 30

What is the common name for the following compound?

Question 31

What is the IUPAC name for the following compound?

Question 32

Arrange the following compounds in decreasing (highest to lowest) order of boiling point.

A) III > I > IV > II
B) I > III > IV > II
C) I > IV > III > II
D) I > III > II > IV
E) III > I > II > IV

Question 33

Which of the following compounds is the strongest base?

A) I
B) II
C) III
D) IV
E) V

Question 34

Arrange the following compounds in decreasing (strongest to weakest) order of basicity.

A) I > III > II > IV
B) II > III > I > IV
C) IV > III > II > I
D) IV > I > II > III
E) II > IV > I > III

Question 35

Identify the weakest base.

A) 4-chloroaniline
B) 4-nitroaniline
C) 4-aminobenzonitrile
D) aniline
E) 4-aminoanisole

Question 36

Arrange the following compounds in decreasing (strongest to weakest) order of basicity.

A) I > III > II > IV
B) II > III > I > IV
C) IV > II > I > III
D) IV > III > II > I
E) II > I > IV > III

Question 37

Arrange the following compounds in decreasing (highest to lowest) order of boiling point.

A) II > III > I
B) I > III > II
C) II > III > I
D) III > II > I
E) I > II > III

Question 38

Rank the following compounds in decreasing (strongest to weakest) order of basicity.

A) I > III > II > IV
B) II > III > I > IV
C) IV > II > III > IV
D) IV > III > II > I
E) III > II > I > IV

Question 39

What is the IUPAC name for the following compound?

Question 40

What is the IUPAC name for the following compound?

Question 41

Provide the reagents necessary to carry out the following conversion.

Question 42

Provide the reagents necessary to carry out the following conversion.

Question 43

Predict the product for the following reaction.

Question 44

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 45

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) III and IV

Question 46

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 47

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 48

Predict the product for the following reaction and provide a stepwise, curved arrow mechanism for the formation of the product.

Question 49

Nicotine, present in tobacco, has the following structure. Which nitrogen is more basic and explain your choice.

Question 50

Predict the product for the following reaction.

Question 51

Predict the product for the following reaction sequence.

Question 52

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 53

Provide the reagents necessary to convert (S)-3-methyl-3-phenylpentanoic acid to (S)-3-methyl-3-phenylpentanamine.

Question 54

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 55

Provide the reagents necessary to carry out the following conversion for the following reaction.

Question 56

Chloroquine is used as an antimalarial drug. Rank the three nitrogen atoms in decreasing (strongest to weakest) order of basicity.

A) III > I > II
B) I > III > II
C) II > I > III
D) I > II > III
E) III > II > I

Question 57

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 58

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 59

Pyridoxamine, aka vitamin B₆, has the following structure. Which nitrogen is more basic? Explain your choice.

Question 60

Provide the reagents necessary to carry out the following conversion.

A) H₂ and Ni
B) 1. LiAlH₄
2) H₂O
C) Fe and HCl
D) Zn and HCl
E) all of these

Question 61

Predict the major product for the following reaction.

A) I
B) II
C) III
D) IV
E) I and III

Question 62

The ________ reaction is used to prepare primary amines by using potassium phthalimide. This reaction proceeds by a ________ mechanism.

Question 63

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 64

Which of these alkyl halides cannot be used to prepare amines using Gabriel synthesis?

A) 1-bromopentane
B) 1-bromo-3-methylbutane
C) 2-bromo-3-methylpentane
D) 1-bromo-2,3-dimethylbutane
E) 2-bromo-2,3-dimethylbutane

Question 65

Provide a stepwise synthesis of 3-amino-2-methylpentane using the Gabriel synthesis.

Question 66

Provide the structures of the products in each step of the following reaction sequence.

Question 67

Provide the reagents necessary to carry out the following conversion.

Question 68

Predict the product for the following reaction sequence.

A) I
B) II
C) III
D) IV
E) V

Question 69

Predict the product(s) for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 70

Predict the product for the following reaction sequence.

A) I
B) II
C) III
D) IV
E) none of these

Question 71

Provide the reagents necessary to carry out the following conversion.

Question 72

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 73

Provide the reagents necessary to carry out the following conversion.

Question 74

Provide the reagents necessary to carry out the following conversion.

Question 75

Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis.

Question 76

Provide the structures of the products in each step of the following reaction sequence.

Question 77

Predict the major product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 78

Predict the product(s) for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 79

Predict the product for the following reaction sequence.

Question 80

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V