Deck 11: Amines and Related Nitrogen Compounds

Question 1

Which compound is the strongest base?

A) CH₃NH₂
B) CH₃CO₂H
C) CH₃CHO
D) CH₃OH
E) C₆H₅NH₂

Answer 1

CH₃NH₂

Question 2

The mechanism by which acylation of an amine with an acid chloride takes place is:

A) nucleophilic acyl substitution
B) electrophilic aromatic substitution
C) nucleophilic addition
D) electrophilic addition
E) nucleophilic aromatic substitution

Answer 2

nucleophilic acyl substitution

Question 3

Which of the following compounds is a tertiary amine?

A)
B)
C)
D)
E)

Answer 3

Question 4

The structure below can be named in the following manner:

A) 2-nitrocyclohexanamine
B) m-nitroaniline
C) o-nitroaniline
D) 2-nitrobenzylamine
E) 1,2-diaminobenzene

Question 5

Which of the following are tertiary amines?

A) 1 and 3
B) only 5
C) 1, 2, 3, and 4
D) 2 and 4
E) 1 and 2

Question 6

Which of the following amines is the most basic?

A) methylamine
B) dimethylamine
C) ammonia
D) aniline
E) N-methylaniline

Question 7

What is the mechanism for the intramolecular alkylation shown below?

A) S_N2
B) S_N1
C) nucleophilic acyl substitution
D) nucleophilic addition
E) electrophilic addition

Question 8

C₆H₅NHCH₂CH₂CH₃ can best be prepared as follows:

A)
B)
C)
D)
E)

Question 9

Which of the following is not an intermediate in the diazotization of aniline using nitrous acid?

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

Question 10

When methylamine (CH₃NH₂) reacts with methyl bromide (CH₃Br) to give dimethylamine, the methylamine:

A) acts as an electrophile
B) acts as a Lewis acid
C) acts as a Bronsted-Lowry acid
D) acts as a Bronsted-Lowry base
E) acts as a nucleophile in an S_N2 reaction

Question 11

The structure that corresponds to N-ethyl-2,3-dimethyl-3-hexanamine is

A)
B)
C)
D)
E)

Question 12

To separate a mixture of p-toluidine and p-nitrotoluene dissolved in ether,

A) extract the ether solution with aqueous HCl and treat the water layer with aqueous NaOH.
B) extract the ether solution with aqueous NaOH and treat the water layer with aqueous HCl.
C) extract the ether solution with water and treat the water layer with aqueous NaOH.
D) extract the ether layer with aqueous HCl and treat the ether layer with aqueous NaOH.
E) extract the ether solution with aqueous HCl and treat the ether layer with aqueous HCl.

Question 13

Tert-butylamine is classified as a(n) amine.

A) 1°
B) 2°
C) 3°
D) quaternary salt
E) aromatic

Question 14

The alkylation of an amine with an alkyl halide takes place by the following mechanism:

A) S_N1
B) S_N2
C) electrophilic addition
D) E1
E) E2

Question 15

The order of decreasing pK_as of the corresponding ammonium ions of the following is:

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

Question 16

The order of increasing basicity of the following is:

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

Question 17

The order of decreasing acidity of the following is:

A) 1 > 2 > 3
B) 3 > 1 > 2
C) 2 > 1 > 3
D) 3 > 2 > 1
E) 2 > 3 > 1

Question 18

What structure represents a cationic intermediate in the electrophilic aromatic bromination of aniline?

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

Question 19

Which of the following molecules has the highest boiling point?

A) ethylamine
B) propane
C) ethyl alcohol
D) dimethyl ether
E) acetaldehyde

Question 20

Which of the following statements is false:

A) Aliphatic 3^o amines with three different groups on nitrogen can be resolved.
B) Primary and secondary aliphatic amines can be hydrogen bond donors.
C) Aliphatic amines can be hydrogen bond acceptors.
D) The non-bonded lone pair in an aliphatic amine is more basic than the non-bonded lone pairs in ethers.
E) The nitrogen in aliphatic amines is sp³-hybridized.

Question 21

What type of products are formed by diazo coupling reactions?

A) meso compounds
B) azo compounds
C) diazonium salts
D) quaternary ammonium salts
E) racemic mixtures

Question 22

Aniline is best prepared via:

A)
B)
C)
D)
E)

Question 23

What reacts with benzenediazonium chloride to produce benzonitrile?

A) HONO
B) Li, NH₃
C) NaBH₃CN
D) KCN, Cu₂CN₂
E) LiAlH₄, ether

Question 24

What is the name of the product formed by reacting CuCl and HCl with benzenediazonium chloride?

A) bromobenzene
B) chlorobenzene
C) o-chloroaniline
D) m-chloroaniline
E) p-chloroaniline

Question 25

The reaction of a 2^o amine with nitrous acid gives:

A) a quaternary ammonium salt
B) a nitrosamine
C) A diazonium salt
D) an azo dye
E) a nitro compound

Question 26

Reacting aniline, C₆H₅NH₂, with a primary alkyl halide will produce a(n):

A) 1° amine
B) 2° amine
C) 3° amine
D) amide
E) imine

Question 27

The product(s) of are:

A)
B)
C)
D)
E)

Question 28

m-Dichlorobenzene can be prepared in good yield by the sequence:

A)
B)
C)
D)
E)

Question 29

What is the final product for the following sequence of reactions?

A)
B)
C)
D)
E)

Question 30

What is the stereochemical relationship of the products formed by reacting racemic lactic acid with (S)-1-phenylethylamine?

A) enantiomers
B) meso compounds
C) racemic mixture
D) diastereomers
E) geometric isomers

Question 31

The amines that can be acylated by acetic anhydride are

A) only 4
B) 1, 2, 3, and 4
C) 1 and 3
D) 2 and 4
E) only 2

Question 32

What is the name of the product of the following reaction?

A) chlorobenzene
B) chloroaniline
C) anilinium chloride
D) o-chloroaniline
E) N-chloroaniline

Question 33

The following reaction sequence will produce:

A)
B)
C)
D)
E)

Question 34

Which molecule is known as an azo compound?

A)
B)
C)
D)
E)

Question 35

An imine is produced when a ketone or aldehyde reacts with:

A) methyl alcohol
B) Zn(Hg), HCl
C) an amine
D) an amide
E) HCN

Question 36

The product(s) from the reaction sequence below is (are):

A)
B)
C)
D)
E)

Question 37

The product(s) from the reaction below are:

A)
B)
C)
D)
E)

Question 38

m-Chlorobromobenzene can be prepared in good yield by the sequence:

A)
B)
C)
D)
E)

Question 39

Which reaction will produce a quaternary ammonium salt?

A)
B)
C)
D)
E)

Question 40

Which of the following amines can be converted to an aryl diazonium salt?

A)
B)
C)
D)
E)