Deck 20: Amines

Question 1

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

Answer 1

(CH₃CH₂CH₂)₄N⁺ Cl ^-

Question 2

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

Answer 2

Dilute HCl

Question 3

Which is a correct common name for the following substance?

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

Answer 3

sec-Butyldiethylamine

Question 4

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 5

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

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

Question 6

What type of amine is pyrrole?

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

Question 7

Arrange the following amines in order of increasing basicity (least to most)in aqueous solution: NH₃
CH₃CH₂CH₂NH₂
(CH₃CH₂CH₂)₂NH
(CH₃CH₂CH₂)₃N
I
II
III
IV

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

Question 8

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

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

Question 9

What type of amine is N-methylmorpholine?

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

Question 10

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 11

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 12

What type of amine is piperidine?

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

Question 13

Which of the following compounds would be the weakest base?

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

Question 14

Which is a correct IUPAC name for the following substance?

A) N-Cyclopentyl-N-methylcylopentanamine
B) N-Cyclohexyl-N-methylcylopentanamine
C) N-Cyclopentyl-N-methylcylohexanamine
D) Dicyclopentylmethylamine
E) N-Pentyl-N-methylpentanamine

Question 15

Which of the following compounds would be the strongest base?

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

Question 16

Which of the following compounds would be the strongest base?

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

Question 17

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

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

Question 18

What type of amine is pyrrolidine?

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

Question 19

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 20

Arrange the following amines in order of decreasing basicity (most to least)in aqueous solution: NH₃
CH₃CH₂CH₂NH₂
(CH₃CH₂CH₂)₂NH
(CH₃CH₂CH₂)₃N
I
II
III
IV

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

Question 21

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

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

Question 22

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

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

Question 23

Which of these is the weakest acid?

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

Question 24

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 25

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 26

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 27

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

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

Question 28

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

Question 29

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 30

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 31

When an equimolar mixture of ammonia and butyl bromide reacts,which of these products will form?

A) Butylamine
B) Dibutylamine
C) Tributylamine
D) Tetrabutylammonium bromide
E) All of these

Question 32

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 33

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 34

In aqueous solution,which of the following bases as the conjugate acid possesses the largest value for pK_a?

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

Question 35

Which would be the weakest base?

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

Question 36

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

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

Question 37

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

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

Question 38

Arrange the following amines in order of decreasing basicity (most to least)in the gas phase: NH₃
CH₃CH₂CH₂NH₂
(CH₃CH₂CH₂)₂NH
(CH₃CH₂CH₂)₃N
I
II
III
IV

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

Question 39

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 40

Which of these is the strongest acid?

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

Question 41

Consider the synthesis below.What is reagent A?

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

Question 42

Which is not an intermediate in the Hofmann degradation reaction?

A) RN=C=O
B)

C)

D)

E)

Question 43

Which is the best method to prepare ?

A)

B)

C)

D)

E)

Question 44

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

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

Question 45

What is the final product,C?

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

Question 46

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

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

Question 47

What would be the product of the following reaction?

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

Question 48

What would be the product of the following reaction sequence?

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

Question 49

Which combination of reactants will not produce ?

A)

B)

C)

D)

E)

Question 50

What would be the product of the following reaction sequence?

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

Question 51

Consider the synthesis below.What is compound B?

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

Question 52

What would be the product of the following reaction?

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

Question 53

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 54

What reagent can effect the following transformation?

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

Question 55

Which of these is the strongest acid?

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

Question 56

The overall conversion RBr -- $\rightarrow$ RCH₂NH₂ can be accomplished by successive application of which of these sets of reagents?

A) Mg,ether;then NH₃
B) NaN₃;then LiAlH₄,ether
C) NaCN;then LiAlH₄,ether
D) H₂C=O;then NH₃
E) H₂NOH;then LiAlH₄,ether

Question 57

What would be the product of the following reaction sequence?

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

Question 58

What would be the product of the following reaction sequence?

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

Question 59

What would be the product of the following reaction sequence?

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

Question 60

What final product is expected when toluene is subjected to the following reaction sequence? i)KMnO₄,NaOH;ii)H₃O⁺;iii)SOCl₂;iv)NaN₃;v)heat

A) C₆H₅CONH₂
B) C₆H₅CH₂NH₂
C) p-CH₃C₆H₄SO₂NH₂
D) p-CH₃C₆H₄NH₂
E) C₆H₅NH₂

Question 61

What would be the product of the following reaction sequence?

A) p-bromobenzamide
B) p-bromobenzaldehyde oxime
C) p-bromobenzenesulfonamide
D) p-bromoaniline
E) 4-bromo-3-chlorobenzoic acid

Question 62

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 63

What is the final product of the reaction sequence:

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

Question 64

What would be the product of the following reaction sequence?

A) p-bromobenzamide
B) p-bromobenzaldehyde oxime
C) p-bromobenzenesulfonamide
D) p-bromoaniline
E) 4-bromo-3-chlorobenzoic acid

Question 65

What would be the product of the following reaction sequence?

A) p-bromobenzamide
B) p-bromobenzaldehyde oxime
C) p-bromobenzenesulfonamide
D) p-bromoaniline
E) 4-bromo-3-chlorobenzoic acid

Question 66

What is the final product of the reaction sequence:

A)

B)

C)

D)

E)

Question 67

What would be the product of the following reaction sequence?

A) p-bromobenzamide
B) p-bromobenzaldehyde oxime
C) p-bromobenzenesulfonamide
D) p-bromoaniline
E) 4-bromo-3-chlorobenzoic acid

Question 68

How could one carry out this synthesis?

A) SOCl₂;then NH₃;then H₃PO₂
B) CH₃Li,ether;then NH₃,H₂,Ni
C) SOCl₂;then NaN₃;then heat
D) PCl₅;then NH₃;then HCl,NaNO₂,0-5°C
E) PCl₅;then CH₃NH₂;then KMnO₄,OH^-,heat

Question 69

What would be the product of the following reaction sequence?

A) p-bromobenzamide
B) p-bromobenzaldehyde oxime
C) p-bromobenzenesulfonamide
D) p-bromoaniline
E) 4-bromo-3-chlorobenzoic acid

Question 70

What is the final product of the reaction sequence:

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

Question 71

How could one carry out this synthesis?

A) SOCl₂;then NH₃;then H₃PO₂
B) CH₃Li,ether;then NH₃,H₂,Ni
C) SOCl₂;then NH₃;then Br₂,NaOH
D) PCl₅;then NH₃;then HCl,NaNO₂,0-5°C
E) PCl₅;then CH₃NH₂;then KMnO₄,OH^-,heat

Question 72

Which product could not be formed during the following reaction?

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

Question 73

What is the final product of the reaction sequence:

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

Question 74

Your task is to convert o-xylene into o-diaminobenzene.Which sequence of reagents constitutes the best method?

A) NaNH₂ and heat
B) NBS/CCl₄;then NH₃;then Br₂/OH^-
C) KMnO₄,OH^-,heat;then H₃O⁺;then PCl₅;then NH₃,then Br₂/OH^-
D) KMnO₄,OH^-,heat;then H₃O⁺;then SOCl₂;then NH₃;then LiAlH₄;then Br₂/OH^-
E) KMnO₄,OH^-,heat;then H₃O⁺;then NH₃ with H₂/Ni

Question 75

What is the final product of the reaction sequence:

A)

B)

C)

D)

E)

Question 76

What is the final product of the reaction sequence:

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

Question 77

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

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

Question 78

What final product is expected when toluene is subjected to the following reaction sequence? i)KMnO₄,NaOH;ii)H₃O⁺ ( product = C₇H₆O₂);iii)SOCl₂;
Iv)NH₃ (product = C₇H₇NO);v)Br₂,NaOH

A) C₆H₅CONH₂
B) C₆H₅CH₂NH₂
C) p-CH₃C₆H₄SO₂NH₂
D) p-CH₃C₆H₄NH₂
E) C₆H₅NH₂

Question 79

When the process ArNH₂ -- $\rightarrow$ 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 80

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