Deck 20: Amines

Question 1

The correct structure of (S)-bicyclo[2.2.1]heptan-2-amine is?

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

Answer 1

III

Question 2

The correct structure of bicyclo[1.1.0]butan-1-amine is?

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

Answer 2

II

Question 3

The correct structure of (S)-N-methylbicyclo[2.2.1]heptan-2-amine is?

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

Answer 3

III

Question 4

Which is a correct common name for the following substance?

A)Ethylethylisobutylamine
B)Diethylisobutylamine
C)sec-Butyldiethylamine
D)Ethylethyl-sec-butylamine
E)2-Diethylaminobutane

Question 5

What type of amine is piperidine?

A)Primary
B)Secondary
C)Tertiary
D)Quaternary
E)None of these choices.

Question 6

What type of amine is quinoline?

A)Primary
B)Secondary
C)Tertiary
D)Quaternary
E)None of these choices.

Question 7

What type of amine is pyrrole?

A)Primary
B)Secondary
C)Tertiary
D)Quaternary
E)None of these choices.

Question 8

The correct structure of bicyclo[1.1.0]butan-2-amine is?

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

Question 9

Which is a correct IUPAC name for the following substance?

A)N-Cyclopentyl-N-methylcyclopentanamine
B)N-Cyclohexyl-N-methylcyclopentanamine
C)N-Cyclopentyl-N-methylcyclohexanamine
D)Dicyclopentylmethylamine
E)N-Pentyl-N-methylpentanamine

Question 10

What type of amine is pyridine?

A)Primary
B)Secondary
C)Tertiary
D)Quaternary
E)None of these choices.

Question 11

Which of these is properly termed a "quaternary ammonium salt"?

A)(CH₃)₃CCH₂CH₂NH₃⁺ Cl^-
B)(CH₃CH₂CH(CH₃)CH₂)₂NH₂⁺ Cl^-
C)(CH₃CH₂CH₂)₃NH⁺ Cl^-
D)(CH₃CH₂CH₂)₄N⁺ Cl^-
E)None of these choices.

Question 12

The aromatic amine purine contains how many nitrogen atoms?

A)1
B)2
C)3
D)4
E)5

Question 13

Which is a correct IUPAC name for the following substance?

A)N-Ethylhexanamine
B)N-Ethylcyclohexanamine
C)N-Cyclohexylethanamine
D)N-Ethylcyclopentanamine
E)N-Ethylaniline

Question 14

Which of these is an acceptable alternative name to "(1-methylbutyl)amine"?

A)2-Aminopentane
B)2-Pentanamine
C)Isopentylamine
D)sec-Pentylamine
E)Both 2-aminopentane and 2-pentanamine

Question 15

What type of amine is indole?

A)Primary
B)Secondary
C)Tertiary
D)Quaternary
E)None of these choices.

Question 16

What type of amine is N-methylmorpholine?

A)Primary
B)Secondary
C)Tertiary
D)Quaternary
E)None of these choices.

Question 17

What type of amine is N-methyl-2-methyl-3-hexanamine?

A)Primary
B)Secondary
C)Tertiary
D)Quaternary
E)None of these choices.

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

The aromatic amine imidazole contains how many nitrogen atoms?

A)1
B)2
C)3
D)4
E)5

Question 20

What type of amine is pyrrolidine?

A)Primary
B)Secondary
C)Tertiary
D)Quaternary
E)None of these choices.

Question 21

Which of these alkyl halides cannot be used effectively in a Gabriel amine 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 22

Compound W has the molecular formula C₁₁H₁₇N.Treatment of W with benzenesulfonyl chloride in base gives no reaction.Acidification of the resulting mixture gives a clear solution.The ¹H NMR spectrum of W consists of: triplet, $\delta$ 1.0
Quartet, $\delta$ 2.5
Singlet, $\delta$ 3.6 (2H)
Multiplet, $\delta$ 7.3 (5H)
The most likely structure for W is:

A)
B)
C)
D)
E)

Question 23

Which reagent will distinguish between 2-amino-2,3-dimethylpentane and 1-amino-3-methyl-2-pentene?

A)HONO,0-5 °C
B)C₆H₅SO₂Cl/OH^-,then H₃O⁺
C)NaOH
D)HCl
E)Br₂/CCl₄

Question 24

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

A)AgNO₃ in H₂O
B)Dilute NaHCO₃
C)Dilute NaOH
D)C₆H₅SO₂Cl/OH^-,then H₃O⁺
E)Dilute HCl

Question 25

The reaction of which of these compounds with nitrous acid results in a stable N-nitroso compound?

A)C₆H₅NH₂
B)C₆H₅N(CH₃)₂
C)CH₃CH₂CH₂CH₂CH₂NH₂
D)C₆H₅NHCH₃
E)CH₃CH₂CONH₂

Question 26

This type of compound is the only one of these which can be converted by reduction into a 1 ^$\circ$ ,2 ^$\circ$ or 3 ^$\circ$ amine,according to its particular structure:

A)Nitrile
B)Oxime
C)Azide
D)Amide
E)Nitroalkane

Question 27

The correct structure of (R)-N-methylbicyclo[2.2.1]heptan-2-amine is?

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

Question 28

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

A)AgNO₃ in H₂O
B)Dilute NaHCO₃
C)Dilute NaOH
D)C₆H₅SO₂Cl/OH^-,then H₃O⁺
E)Dilute HCl

Question 29

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

A)AgNO₃ in H₂O
B)Dilute NaHCO₃
C)Dilute NaOH
D)C₆H₅SO₂Cl/OH^-,then H₃O⁺
E)Dilute HCl

Question 30

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

A)AgNO₃ in H₂O
B)Dilute NaHCO₃
C)Dilute NaOH
D)C₆H₅SO₂Cl/OH^-,then H₃O⁺
E)Dilute HCl

Question 31

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

A)AgNO₃ in H₂O
B)Dilute NaHCO₃
C)Dilute NaOH
D)C₆H₅SO₂Cl/OH^-,then H₃O⁺
E)Dilute HCl

Question 32

When the process ArNH₂ $\to$ ArY is carried out via an intermediate diazonium salt,this salt is isolated only in the case in which Y is which of these groups?

A)-F
B)-Cl
C)-Br
D)-I
E)-CN

Question 33

Which of the following compounds would be the strongest base?

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

Question 34

What is the basis for the successful resolution of racemic C₆H₅CHOHCO₂H through use of the chiral amine,C₆H₅CH(NH₂)CH₃?

A)One enantiomer is more soluble than the other.
B)The racemic mixture is converted into a single isomer in the basic solvent.
C)The diastereomeric salts formed have different solubilities.
D)The diastereomeric salts have different boiling points.
E)The diastereomeric salts have different melting points.

Question 35

Which of these compounds is expected to possess the lowest boiling point?

A)CH₃CH₂CH₂CH₂CH₂NH₂
B)CH₃CH₂CH₂NHCH₂CH₃
C)(CH₃CH₂)₂NCH₃
D)(CH₃CH₂)₂CHOH
E)(CH₃)₃CCH₂NH₃⁺ Cl^-

Question 36

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

A)AgNO₃ in H₂O
B)Dilute NaHCO₃
C)Dilute NaOH
D)C₆H₅SO₂Cl/OH^-,then H₃O⁺
E)Dilute HCl

Question 37

Which is not an intermediate in the Hofmann degradation reaction?

A)RN=C=O
B)
C)
D)
E)

Question 38

Which reagent could be used to separate a mixture of aniline and toluene?

A)KMnO₄ in H₂O
B)Dilute NaOH
C)Dilute NaHCO₃
D)Ag(NH₃)₂OH
E)Dilute HCl

Question 39

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

A)Tollens' test
B)Dilute NaHCO₃
C)Hinsberg test
D)Iodoform test
E)None of these choices.

Question 40

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

A)AgNO₃ in H₂O
B)HONO,0-5 °C then $\beta$ -naphthol
C)Dilute NaOH
D)C₆H₅SO₂Cl and OH^- in H₂O
E)Dilute HCl

Question 41

Which of the following aryl amines is the strongest base?

A)Aniline
B)p-Trimethylammonium aniline
C)p-Methoxyaniline
D)p-Trifluoromethylaniline
E)p-Chloroaniline

Question 42

Which of the following bases has a conjugate acid with the smallest pK_a?

A)p-Methylaniline
B)p-Methoxyaniline
C)Hexylamine
D)p-Nitroaniline
E)Dipropylamine

Question 43

Arrange the following compounds in order of increasing basicity (least to most)in aqueous solution:

A)IV < II < I < III
B)III < II < IV < I
C)II < I < III < IV
D)II < III < I < IV
E)Cannot be determined from information given

Question 44

Which of these would be predicted to have the largest pK_a?

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

Question 45

Which of these is the weakest acid?

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

Question 46

Arrange the following compounds in order of increasing basicity (least to most)in aqueous solution:

A)IV < II < I < III
B)III < II < IV < I
C)II < I < III < IV
D)II < III < I < IV
E)Cannot be determined from information given

Question 47

Arrange the following amines in order of decreasing basicity (most to least)in aqueous solution:

A)IV > II > I > III
B)III > II > IV > I
C)III > I > II > IV
D)II > III > I > IV
E)Cannot be determined from information given

Question 48

Which of these would be predicted to have the smallest pK_a?

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

Question 49

Which of the following compounds would be the weakest base?

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

Question 50

Which of the following compounds would be the strongest base?

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

Question 51

Which of the following bases has a conjugate acid with the smallest pK_a?

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

Question 52

Which of the following bases has a conjugate acid with the largest pK_a?

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

Question 53

Which of the following aryl amines is the weakest base?

A)Aniline
B)p-Trimethylammonium aniline
C)p-Methoxyaniline
D)p-Trifluoromethylaniline
E)p-Chloroaniline

Question 54

Which would be the weakest base?

A)p-Methylaniline
B)p-Methoxyaniline
C)Hexylamine
D)p-Nitroaniline
E)Dipropylamine

Question 55

In aqueous solution,which of the following bases has the conjugate acid that possesses the smallest value for pK_a?

A)C₆H₅NH₂
B)NH₃
C)(CH₃CH₂)₃N
D)(CH₃CH₂)₂NH
E)CH₃CH₂CH₂NH₂

Question 56

Which of these is the strongest acid?

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

Question 57

Which of the following bases has a conjugate acid with the smallest pK_a?

A)I
B)II
C)III
D)IV
E)Cannot be determined from information given

Question 58

Which of these is the strongest acid?

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

Question 59

Arrange the following amines in order of increasing basicity (least to most)in aqueous solution:

A)IV < II < I < III
B)III < II < IV < I
C)III < I < II < IV
D)II < III < I < IV
E)Cannot be determined from information given

Question 60

Which of these compounds is soluble in dilute sodium hydroxide solution?

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

Question 61

Identify the best method(s)to prepare .

A)
B)
C)

D) and

E) and

Question 62

Which of the following can be used to prepare allylamine (pure)?

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

Question 63

Which of the following can be used to prepare benzylamine (pure)?

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

Question 64

Consider the synthesis below.What is reagent A?

A)H₃PO₂
B)HCN
C)P₄O₁₀
D)CuCN
E)CuCl₂

Question 65

Identify the best method(s)to prepare N-methylphenylmethanamine.

A)
B)
C)

D) and

E) and

Question 66

What reagent can effect the following transformation?

A)Sn/HCl; then OH^-
B)NH₂Cl
C)H₃PO₂
D)CuCN
E)HONO; then NH₃

Question 67

Which is the best method to prepare 1-phenylethanamine?

A)
B)

C)

D)

E)

Question 68

Identify the best method(s)to prepare N-methylphenylmethanamine.

A)
B)
C)

D) and

E) and

Question 69

Consider the synthesis below.What is compound B?

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

Question 70

What reagent can effect the following transformation?

A)Fe/HCl; then OH^-
B)NH₂Cl
C)H₃PO₂
D)CuCN
E)HONO; then NH₃

Question 71

Which is the best method to prepare ?

A)
B)

C)

D)

E)

Question 72

Consider the synthesis below.What is reagent "Y"?

A)Br₂/FeBr₃
B)CuBr
C)CuBr₂
D)H₃PO₂/H₂O
E)H₃PO₄

Question 73

Identify the best method(s)to prepare N-methylphenylmethanamine.

A)
B)
C)

D) and

E) and

Question 74

Which is the best method to prepare 1-phenylethanamine?

A)
B)

C)

D)

E)

Question 75

Which of the following reactions would yield C₆H₅CH₂NH₂?

A)

B)
C)

D)All of these choices.
E)Two of these choices.

Question 76

Consider the synthesis below.What is reagent A?

A)Br₂,FeBr₃
B)Fe,HCl; then OH^-
C)NH₂Cl,AlCl₃
D)H₃PO₂
E)LiNH₂

Question 77

Consider the synthesis below.What is reagent "Z"?

A)CuCl
B)CuCl₂
C)NaCl
D)KCl
E)HCl/heat

Question 78

Which of these could be resolved into separate enantiomers?

A)4-Methyl-1-pentanamine
B)4-Methyl-2-pentanamine
C)N-Methyl-1-butanamine
D)N,N-Dimethyl-1-propanamine
E)N-Butyltrimethylammonium bromide

Question 79

Consider the synthesis below.What is reagent C?

A)excess Br₂,H₂O
B)Fe,HCl; then OH^-
C)NH₂Cl,AlCl₃
D)CuBr
E)HNO₃,H₂SO₄,Fe

Question 80

Which of the following can be used to prepare 2-aminopentane (pure)?

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