Deck 23: Amines

Question 1

What is the common name for the following compound?

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

Answer 1

ethylisobutylisopropylamine

Question 2

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

Answer 2

CH₃CH₂CH₂CH₂NH₂

Question 3

What is the IUPAC name for the following compound?

Answer 3

4-amino-2,2-diethylhexanoic acid

Question 4

What is the structure for N-ethylbenzylamine?

Question 5

What is the structure for 3-chloro-N-ethylpentanamine?

Question 6

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 7

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) none of these

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 IUPAC name for the following compound?

Question 10

What is the IUPAC name for the following compound?

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

Question 11

What is the common name for the following compound?

A) ethylethylisobutylamine
B) diethylisobutylamine
C) sec-butyldiethylamine
D) 2-diethylaminobutane
E) none of these

Question 12

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

Question 13

What is the IUPAC name for the following compound?

Question 14

What is the IUPAC name for the following compound?

Question 15

What is the IUPAC name for the following compound?

Question 16

What is the common name for the following compound?

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

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

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 19

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 20

What is the structure for N,N-diethylaniline?

Question 21

Predict the product for the following reaction.

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

Question 22

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 23

Which of the following compounds is least soluble in water?

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

Question 24

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 25

Predict the product for the following reaction.

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

Question 26

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 27

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

Question 28

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

Question 29

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 30

Arrange the following amines in decreasing (most to least) order of solubility in water.

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

Question 31

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

A) IVB) IIIC) IID) IIE) None of

Question 32

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 33

Which of the following compounds is the strongest base?

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

Question 34

What is the IUPAC name for the following compound?

Question 35

What is the IUPAC name for the following compound?

Question 36

Which of the following compounds is most soluble in water?

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

Question 37

Predict the product for the following reaction.

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

Question 38

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) I>IV>III>II
D) I>III>II>IV
E) III>II>I

Question 39

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 40

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

Question 41

Predict the product for the following reaction.

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

Question 42

Provide the reagents necessary to carry out the following conversion.

Question 43

Predict the product(s) for the following reaction.

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

Question 44

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

Question 45

Predict the product for the following reaction sequence.

Question 46

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

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

Predict the product for the following reaction sequence.

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

Question 50

Predict the product(s) for the following reaction.

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

Question 51

Provide the reagents necessary to carry out the following conversion.

Question 52

Predict the product for the following reaction.

Question 53

Predict the product(s) for the following reaction.

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

Question 54

Provide the reagents necessary to carry out the following conversion.

Question 55

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 56

Predict the product for the following reaction.

Question 57

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

Question 58

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

Question 59

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

Question 60

Provide the reagents necessary to carry out the following conversion.

Question 61

Predict the major product for the following reaction.

Question 62

Provide the reagents necessary to carry out the following conversion.

Question 63

Predict the major product for the following reaction.

Question 64

Provide the reagents necessary to carry out the following conversion.

Question 65

Provide the reagents necessary to carry out the following conversion.

Question 66

Provide the reagents necessary to carry out the following conversion.

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) none of these

Question 69

Provide a stepwise synthesis to carry out the following conversion.

Question 70

Predict the major product for the following reaction.

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

Question 71

Provide the reagents necessary to carry out the following conversion.

Question 72

Provide the reagents necessary to carry out the following conversion.

Question 73

Predict the major product for the following reaction.

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

Question 74

Provide the reagents necessary to carry out the following conversion.

Question 75

Provide the reagents necessary to carry out the following conversion.

Question 76

Provide the reagent A, necessary to carry out the following conversion.

A) H₃PO₂
B) HCN
C) H₂O
D) CH₃OH, heat
E) NaOCH₃

Question 77

Provide the reagent A, necessary to carry out the following conversion.

A) Br₂/FeBr₃
B) CuBr
C) NaOH
D) H₃PO₂
E) H₃PO₄

Question 78

Predict the major product for the following reaction.

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

Question 79

Provide the reagents necessary to carry out the following conversion.

Question 80

Provide the reagents necessary to carry out the following conversion.