Deck 23: 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 IUPAC name for the following compound?

Answer 2

4-amino-2,2-diethylhexanoic acid

Question 3

What is the IUPAC name for the following compound?

Answer 3

(1S,2S)-2-methyl-1-cyclopentanamine

Question 4

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 5

What is the IUPAC name for the following compound?

Question 6

Which one of the following compounds is the strongest base?

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

Question 7

What is the structure for N-ethylbenzylamine?

Question 8

What is the IUPAC name for the following compound?

Question 9

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 10

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

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

Question 11

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 12

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 13

What is the common name for the following compound?

A)ethylethylisobutyl amine
B)diethylisobutyl amine
C)sec-butyldiethylamine
D)2-diethylaminobutane
E)None of these

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 IUPAC name for the following compound?

Question 17

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

Question 18

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 19

What is the structure for N,N-diethylaniline?

Question 20

What is the IUPAC name for the following compound?

A)N-cyclopentyl-N-methylcylohexanamine
B)N-cyclohexyl-N-methylcylohexanamine
C)N-cyclopentyl-N-methylcylopentanamine
D)cyclohexylcyclopentylmethylamine
E)N-pentyl-N-methylhexanamine

Question 21

Predict the product for the following reaction.

Question 22

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

Question 23

Predict the product(s)for the following reaction.

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

Question 24

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 25

Predict the product(s)for the following reaction.

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

Question 26

Predict the product(s)for the following reaction.

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

Question 27

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

Question 28

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

Question 29

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 30

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 31

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

Question 32

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

Question 33

Provide the reagents necessary to carry out the following conversion.

Question 34

Predict the product for the following reaction sequence.

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

Question 35

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

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

Question 37

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

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

Question 38

Predict the product for the following reaction.

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

Question 39

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

Question 40

Predict the product for the following reaction.

Question 41

Predict the major product for the following reaction.

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

Question 42

Provide the reagents necessary to carry out the following conversion.

Question 43

Provide the reagents necessary to carry out the following conversion.

Question 44

Predict the major product for the following reaction.

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

Question 45

Predict the product for the following reaction.

Question 46

Provide the reagents necessary to carry out the following conversion.

Question 47

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

Question 48

Predict the major product for the following reaction.

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

Question 49

Predict the product for the following reaction sequence.

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

Question 50

Provide a stepwise synthesis to carry out the following conversion.

Question 51

Provide the reagents necessary to carry out the following conversion.

Question 52

Predict the major product for the following reaction.

Question 53

Provide the reagents necessary to carry out the following conversion.

Question 54

Provide the reagents necessary to carry out the following conversion.

Question 55

Predict the major product for the following reaction.

Question 56

Provide a stepwise synthesis to carry out the following conversion.

Question 57

Predict the major product for the following reaction.

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

Question 58

Predict the major product for the following reaction.

Question 59

Predict the major product for the following reaction.

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

Question 60

Predict the major product for the following reaction.

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

Question 61

A compound with molecular formula C₈H₁₀BrN exhibits a singlet at $\delta$ 1.2 (I=2),a triplet at $\delta$ 2.8 (I=2),a triplet at $\delta$ 3.0 (I=2),a doublet at $\delta$ 7.1 (I=2)and a doublet at $\delta$ 7.4 (I=2)in its ¹HNMR spectrum.Its IR spectrum shows two medium absorption bands near 3400 cm^-1.What is the structure for this compound?

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

Question 62

A compound with molecular formula C₆H₁₅N exhibits a triplet at $\delta$ 0.9 (I=6),a singlet at $\delta$ 1.3 (I=1),a sextet at $\delta$ 1.5 (I=4),and a triplet at $\delta$ 2.6 (I=4)in its ¹HNMR spectrum.Its IR spectrum shows medium absorption band near 3400 cm^-1.Its ¹³CNMR spectrum showed peaks at $\delta$ 11,25 and 52.What is the structure for this compound?

Question 63

A compound with molecular formula C₇H₁₇N exhibits a triplet at $\delta$ 1.0 (I=3),a doublet at $\delta$ 1.1 (I=6),a multiplet at $\delta$ 2.0 (I=1),a singlet at $\delta$ 2.3 (I=3),a doublet at $\delta$ 2.3 (I=2),and a quartet at $\delta$ 2.4 (I=2)in its ¹HNMR spectrum.Its ¹³CNMR spectrum showed peaks at $\delta$ 13.4,20,27.9,39.3,49.5 and 65.2.What is the structure for this compound?

Question 64

A compound with molecular formula C₄H₁₁N exhibits a triplet at $\delta$ 0.9 (I=3),a doublet at $\delta$ 1.1 (I=3),a quintet at $\delta$ 1.4 (I=2),a singlet at $\delta$ 1.7 (I=2)and a sextet at $\delta$ 2.8 (I=2)in its ¹HNMR spectrum.Its IR spectrum shows two medium absorption bands near
3400 cm^-1.What is the structure for this compound?

Question 65

Predict the major product when pyridine is treated with a mixture of nitric acid and sulfuric acid.

A)3-nitropyridine
B)2-nitropyridine
C)4-nitropyridine
D)2,3-dinitropyridine
E)4-aminopyridine