General, Organic, and Biological Chemistry, 3e (Timberlake)

Chapter 18 Amines and Amides

18.1 Multiple Choice Questions

1) The compound CH3CH2NH CH3 is classified as a
A) primary amine.
B) secondary amine.
C) tertiary amine.
D) quaternary amine.
E) hydrated amine.
Answer: B

2) The compound CH3CH2NH2 is classified as a

A) primary amine.
B) secondary amine.
C) tertiary amine.
D) quaternary amine.
E) hydrated amine.
Answer: A

3) Which of the following compounds is an amine?

A) (CH3CH2)2NH
B) CH3CH2CH2CH2CO2CH3
C) CH3CH2CH2CH2-O-CH2CH2CH3
D) CH3CH=O
E) CH3COCH3
Answer: A

4) Which of the following compounds CANNOT form hydrogen bonds with water?
A) CH3CH2CH3

B) CH3CH2OH

C) O
||
CH3COH

D) O
||
CH3COCH3

E) CH3CH2NH2

Answer: A

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5) Which of the following compounds CANNOT form hydrogen bonds with water?
A) (CH3CH2)2NH
B) CH3CH2OH
C) (CH3CH2)3N
D) CH3CH2NH2
E) All of the compounds above are capable of forming hydrogen bonds with water.
Answer: C

6) Name the following compound.

CH3 – NH
|
CH3
A) ethyl amine
B) dimethyl ether
C) methanal
D) 1-methanoate
E) dimethyl amine
Answer: E

7) What is the name of this compound?

A) 1-methyl-5-bromoaniline
B) N-methyl-3-bromoaniline
C) N-methyl-p-bromoaniline
D) 1-bromo-3-N-methylamine benzene
E) 1-bromo-3-N-methyl aniline
Answer: B

8) Aminobenzene is properly known as

A) toluene.
B) aniline.
C) amidine.
D) histidine.
E) phenylamine.
Answer: B

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 9) What is the name of this compound?

CH3N CH2CH3
|
CH3

A) trimethylamine
B) diethylamine
C) ethylmethylamine
D) ethylmethylnitride
E) ethyldimethylamine
Answer: E

10) In response to allergic reactions or injury to cells, the body increases the production of
A) diphenhydramine.
B) antihistamine.
C) histamine.
D) epinephrine.
E) dopamine.
Answer: C

11) Which of the following represents the complete neutralization of N,N-dimethylamine?

A)

B)

C)

D)

E)

Answer: E

12) When ethylamine dissolves in water, a solution of __________ is produced.

A) ammonia
B) ethylammonium hydroxide
C) ethylamine
D) ethylhydroxide
E) ethylhydroxylate
Answer: B

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13) Diethylamine and HCl react to produce
A) diethyl chloride.
B) diethylammonium chloride.
C) ethylammonium chloride.
D) ammonium chloride.
E) butylammonium chloride.
Answer: B

14) The amide formed in the reaction of benzoic acid and ethylamine is
A)

B)

C)

D)

E)

Answer: B

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15) When acetic acid reacts with ammonia, NH3, the reaction called amidation yields
A) acetamine.
B) ammonium acetate.
C) ethylammonium hydroxide.
D) amino acetate.
E) acetamide.
Answer: E

16) Physiologically active nitrogen-containing compounds produced by plants are called

A) aromatics.
B) alkaloids.
C) esters.
D) polymers.
E) ethers.
Answer: B

17) Which of the following is NOT an alkaloid?

A) nicotine
B) caffeine
C) diethylamine
D) quinine
E) cocaine
Answer: C

18) What is the major functional group in the following compound?

O
||
CH3CNHCH3

A) ketone
B) carboxylic acid
C) ester
D) amine
E) amide
Answer: E

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19) What is the name of this compound?

A) 1-ethylbenzamide
B) N,N-dimethylbenzamide
C) 2-ethylbenzamide
D) N-ethylbenzamide
E) ethylaminobenzoic acid
Answer: D

20) One name for this compound is

CH3CH2-C-NH-CH2CH3

A) N-ethylpropanamide.
B) N-ethylacetamide.
C) pentanamide.
D) N,N-diethylacetamide.
E) ethylpropionamide.
Answer: A

21) In the formation of N-ethylacetamide, the reactant(s) is(are)

A) acetic acid and dimethylamine.
B) diethylamine.
C) acetamide and ethanol.
D) acetic acid and ethylamine.
E) ethanol and ethylamine.
Answer: D

22) The reaction of butanoic acid and dimethylamine gives

A) N-methylbutanamide.
B) N-ethylbutanamide.
C) N,N-dimethylbutanamide.
D) N,N-methylbutanamine.
E) N-methylbutanamine.
Answer: C

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23) Which of the following is the reaction for the acid hydrolysis of N-methylacetamide?
A)

B)

C)

D)

E)

Answer: E

24) Which of the following is the reaction for the base hydrolysis of N-ethylformamide?
A)

B)

C)

D)

E)

Answer: B

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25) With the correct choice of acid, acid hydrolysis of acetamide could produce
A) acetic acid and ammonium chloride.
B) acetic acid and methylamine.
C) ethanol and ammonia.
D) acetaldehyde and ammonium hydroxide.
E) formic acid and ethylamine.
Answer: A

26) With the correct choice of acid, the product(s) of the acid hydrolysis of N-methylbenzamide
could be
A) formic acid and aniline.
B) methanol and benzoic acid.
C) benzoic acid and ethylamine.
D) benzoic acid and methylammonium chloride.
E) formic acid, phenol, and ammonia.
Answer: D

27) Amines contain the element

A) nitrogen.
B) oxygen.
C) sulfur.
D) astatine.
E) arginine.
Answer: A

28) In what kind of amine is the nitrogen directly bonded to two carbon atoms?
A) primary
B) secondary
C) tertiary
D) quaternary
E) amide
Answer: B

29) Which chemical class does phenobarbital belong to?

A) ester
B) amine
C) amide
D) alkane
E) ether
Answer: C

30) What functional group is always found in alkaloids (such as caffeine, nicotine, and digitalis)?
A) amide
B) acid
C) ether
D) amine
E) ester
Answer: D

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31) When naming amines according to the IUPAC system, the -e in the corresponding alkane is
replaced with
A) -amide.
B) -amine.
C) -ine.
D) -ide.
E) -ane.
Answer: B

32) Cyclic compounds that contain a nitrogen atom are called

A) carbocyclic compounds.
B) aromatic compounds.
C) heterocyclic compounds.
D) homocyclic compounds.
Answer: C

33) Aniline is a(n)

A) primary aromatic amine.
B) secondary aromatic amine.
C) heterocyclic amine.
D) aliphatic amine.
E) tertiary amine.
Answer: A

34) What prefix is used to show that a small alkyl group is attached to the nitrogen of aniline and
not to the aromatic ring?
A) N-
B) C-
C) Roman numerals
D) Greek letters
E) iso-
Answer: A

35) How many alkyl substituents does N-ethyl-N-methylaniline have?

A) one
B) two
C) three
D) eight
E) none
Answer: B

36) Diphenhydramine (Benadryl®) contains both __________ and __________ functional groups.
A) ester; acid
B) ether; amine
C) ester; amine
D) ether; amide
E) acid; amide
Answer: B

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37) What pharmacologic activity do amphetamine, phenylephrine, and methedrine have in
common?
A) CNS depressant
B) antidepressant
C) appetite stimulant
D) CNS stimulant
E) sedative
Answer: D

38) What pharmacologically active amine is responsible for the signs and symptoms encountered
in an allergic reaction?
A) histamine
B) epinephrine
C) diphenhydramine
D) phenylephrine
E) dopamine
Answer: A

39) A deficiency of which amine is responsible for the signs and symptoms of Parkinson's
disease?
A) histamine
B) dopamine
C) epinephrine
D) diphenhydramine
E) methedrine
Answer: B

40) The prefix nor- in a drug name means that there is

A) one more amine in the new molecule than in the original.
B) one more methyl group on the nitrogen atom in the new molecule than in the original.
C) one less methyl group on the nitrogen atom in the new molecule than in the original.
D) one less amine in the new molecule than in the original.
E) one less double bond in the new molecule than in the original.
Answer: C

41) What relation does the boiling point of an amine have to a similar hydrocarbon?
A) higher
B) lower
C) very similar
Answer: A

42) Amines can form __________ bonds with other molecules.

A) oxygen
B) hydrogen
C) nonpolar
D) metallic
E) triple
Answer: B

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43) What kind of amine CANNOT form hydrogen bonds?
A) primary
B) secondary
C) tertiary
D) aromatic
E) substituted
Answer: C

44) Amines are

A) Bronsted-Lowry bases.
B) Bronsted-Lowry acids.
C) neutral in water solution.
D) unreactive.
Answer: A

45) The odor of an amine can be neutralized with

A) water.
B) acids.
C) bases.
D) detergents.
E) solvents.
Answer: B

46) Choline is a quaternary ammonium compound with a __________ charge on the nitrogen.
A) positive
B) negative
C) zero
D) neutral
E) double
Answer: A

47) In what form are amine-containing drugs often administered?

A) free base
B) sodium salt
C) amine salt
D) water solution
E) oil solution
Answer: C

48) What kind of pharmacologic activity is found in the amines Procaine ® and Lidocaine®?
A) stimulant
B) general anesthetic
C) local anesthetic
D) disinfectant
E) fungicide
Answer: C

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49) What are alkaloids?
A) physiologically active nitrogen compounds derived from plants
B) anesthetics found in plants
C) flavoring agents found in fruits and vegetables
D) preservatives found in animal tissue
E) natural steroids
Answer: A

50) Identify the heterocyclic amine in the choices below.

A) diphenhydramine
B) pyrrolidine
C) adrenaline
D) methylamine
E) cholesterol
Answer: B

51) Among the choices below, identify the heterocyclic amine found in DNA.
A) piperidine
B) pyridine
C) pyrrole
D) purine
E) imidazole
Answer: D

52) Nicotine, coniine, quinine, atropine, and morphine are all examples of
A) ethers.
B) esters.
C) carboxylic acids.
D) alkaloids.
E) amides.
Answer: D

53) Procaine® and Lidocaine® were developed by modifying the structure of

A) cocaine.
B) nicotine.
C) harmaline.
D) meperidine.
E) caffeine.
Answer: A

54) Amides are derivatives of __________ and __________.

A) amines; esters
B) amines; acids
C) alkanes; amines
D) acids; alcohols
E) alcohols; acids
Answer: B

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55) What kind of compound is urea?
A) ester
B) acid
C) amide
D) ketone
E) amine
Answer: C

56) What is the chemical classification of the barbiturate sedatives?

A) cyclic amides
B) cyclic ethers
C) cyclic amines
D) cyclic esters
E) cyclic acids
Answer: A

57) Valium®, first synthesized by Leo Sternbach at Hoffman-LaRoche, is chemically classified as

a(n)
A) amine.
B) ether.
C) heterocyclic amide.
D) ester.
E) alcohol.
Answer: C

58) Amides having fewer than __________ carbons are generally water soluble.
A) five
B) six
C) ten
D) eleven
E) twelve
Answer: A

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