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General, Organic & Biological Chemistry, 5e (Timberlake)
Chapter 18 Amines and Amides
18.1 Multiple Choice Questions
1) The compound CH3 - CH2 - NH - CH3 is classified as a
A) primary amine.
B) secondary amine.
C) tertiary amine.
D) quaternary amine.
E) hydrated amine.
Answer: B
Objective: 18.1
Global Outcomes: GO2
2) The compound CH3 - CH2 - NH2 is classified as a
A) primary amine.
B) secondary amine.
C) tertiary amine.
D) quaternary amine.
E) hydrated amine.
Answer: A
Objective: 18.1
Global Outcomes: GO2
3) Which of the following compounds is an amine?
A) (CH3 - CH2)2NH
B) CH3 - CH2 - CH2 - CH2 - CO2 - CH3
C) CH3 - CH2 - CH2 - CH2 - O - CH2 - CH2 - CH3
D) CH3 - CH = O
E) CH3 - CO - CH3
Answer: A
Objective: 18.1
Global Outcomes: GO2
1
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4) 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
Objective: 18.1
Global Outcomes: GO2
5) Aminobenzene is properly known as
A) toluene.
B) aniline.
C) amidine.
D) histidine.
E) phenylamine.
Answer: B
Objective: 18.1
Global Outcomes: GO2
6) What is the name of this compound?
CH3 - N - CH2 - CH3
|
CH3
A) trimethylamine
B) diethylamine
C) ethylmethylamine
D) ethylmethylnitride
E) ethyldimethylamine
Answer: E
Objective: 18.1
Global Outcomes: GO2
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7) Name the following compound.
A) ethyl amine
B) dimethyl ether
C) methanal
D) 1-methanoate
E) dimethyl amine
Answer: E
Objective: 18.1
Global Outcomes: GO2
8) Amines contain the element
A) nitrogen.
B) oxygen.
C) sulfur.
D) astatine.
E) arginine.
Answer: A
Objective: 18.1
Global Outcomes: GO2
9) 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
Objective: 18.1
Global Outcomes: GO2
10) 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
Objective: 18.1
Global Outcomes: GO2
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11) Aniline is a(n)
A) primary aromatic amine.
B) secondary aromatic amine.
C) heterocyclic amine.
D) aliphatic amine.
E) tertiary amine.
Answer: A
Objective: 18.1
Global Outcomes: GO2
12) 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) NB) CC) Roman numerals
D) Greek letters
E) isoAnswer: A
Objective: 18.1
Global Outcomes: GO2
13) How many alkyl substituents does N-ethyl-N-methylaniline have?
A) one
B) two
C) three
D) eight
E) none
Answer: B
Objective: 18.1
Global Outcomes: GO2
14) What is the common name of the following compound?
A) ethyl propyl amine
B) diethyl amine
C) trimethyl amine
D) propyl amino
E) dipropyl amine
Answer: A
Objective: 18.1
Global Outcomes: GO2
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15) What is the IUPAC name of the following compound?
A) propyl amine
B) butyl amine
C) amine butane
D) 1-aminobutane
E) 1-aminopropane
Answer: D
Objective: 18.1
Global Outcomes: GO2
16) Which of the following compounds CANNOT form hydrogen bonds with water?
A) CH3 - CH2 - CH3
B) CH3 - CH2 - OH
C)
O
CH3 - C - OH
D)
O
CH3 - C - O - CH3
E) CH3 - CH2 - NH2
Answer: A
Objective: 18.2
Global Outcomes: GO2
17) Which of the following compounds CANNOT form hydrogen bonds with water?
A) (CH3 - CH2)2NH
B) CH3 - CH2 - OH
C) (CH3 - CH2)3N
D) CH3 - CH2 - NH2
E) All of the compounds above are capable of forming hydrogen bonds with water.
Answer: C
Objective: 18.2
Global Outcomes: GO2
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18) Which of the following represents the complete neutralization of N,N-dimethylamine?
A) CH3NH + H2O →
CH3NH2+ + OH|
CH3
|
CH3
→
B) CH3NH + NaOH
|
CH3
C) CH3NH + HCl
CH3N-Na+ + H2O
|
CH3
→ CH3NH2 + CH3Cl
|
CH3
D) CH3NH + H2O → CH3OH + CH3NH2
|
CH3
E) CH3NH + HCl
|
CH3
→
CH3NH2+ + Cl|
CH3
Answer: E
Objective: 18.2
Global Outcomes: GO2
19) When ethylamine dissolves in water, a solution of ________ is produced.
A) ammonia
B) ethylammonium hydroxide
C) ethylamine
D) ethylhydroxide
E) ethylhydroxylate
Answer: B
Objective: 18.2
Global Outcomes: GO2
20) Diethylamine and HCl react to produce
A) diethyl chloride.
B) diethylammonium chloride.
C) ethylammonium chloride.
D) ammonium chloride.
E) butylammonium chloride.
Answer: B
Objective: 18.2
Global Outcomes: GO2
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21) What relation does the boiling point of an amine have to a similar hydrocarbon?
A) higher
B) lower
C) very similar
Answer: A
Objective: 18.2
Global Outcomes: GO2
22) Amines can form ________ bonds with other molecules.
A) oxygen
B) hydrogen
C) nonpolar
D) metallic
E) triple
Answer: B
Objective: 18.2
Global Outcomes: GO2
23) What kind of amine can NOT form hydrogen bonds?
A) primary
B) secondary
C) tertiary
D) aromatic
E) substituted
Answer: C
Objective: 18.2
Global Outcomes: GO2
24) Amines are
A) Bronsted-Lowry bases.
B) Bronsted-Lowry acids.
C) neutral in water solution.
D) unreactive.
Answer: A
Objective: 18.2
Global Outcomes: GO2
25) The odor of an amine can be neutralized with
A) water.
B) acids.
C) bases.
D) detergents.
E) solvents.
Answer: B
Objective: 18.2
Global Outcomes: GO2
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26) Choline is a quaternary ammonium compound with a ________ charge on the nitrogen.
A) positive
B) negative
C) zero
D) neutral
E) double
Answer: A
Objective: 18.2
Global Outcomes: GO2
27) In what form are amine-containing drugs often administered?
A) free base
B) sodium salt
C) ammonium salt
D) water solution
E) oil solution
Answer: C
Objective: 18.2
Global Outcomes: GO7
28) What kind of pharmacologic activity is found in the amines Procaine and Lidocaine?
A) stimulant
B) anesthetic
C) local anesthetic
D) disinfectant
E) fungicide
Answer: C
Objective: 18.3
Global Outcomes: GO7
29) 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
Objective: 18.3
Global Outcomes: GO2
30) Identify the heterocyclic amine in the choices below.
A) diphenhydramine
B) pyrrolidine
C) adrenaline
D) methylamine
E) cholesterol
Answer: B
Objective: 18.3
Global Outcomes: GO2
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31) Among the choices below, identify the heterocyclic amine found in DNA.
A) piperidine
B) pyridine
C) pyrrole
D) purine
E) imidazole
Answer: D
Objective: 18.3
Global Outcomes: GO2
32) Nicotine, coniine, quinine, atropine, and morphine are all examples of
A) ethers.
B) esters.
C) carboxylic acids.
D) alkaloids.
E) amides.
Answer: D
Objective: 18.3
Global Outcomes: GO7
33) Procaine and Lidocaine were developed by modifying the structure of
A) cocaine.
B) nicotine.
C) harmaline.
D) meperidine.
E) caffeine.
Answer: A
Objective: 18.3
Global Outcomes: GO7
34) Physiologically active nitrogen-containing compounds produced by plants are called
A) aromatics.
B) alkaloids.
C) esters.
D) polymers.
E) ethers.
Answer: B
Objective: 18.3
Global Outcomes: GO2
35) Which of the following is NOT an alkaloid?
A) nicotine
B) caffeine
C) diethylamine
D) quinine
E) cocaine
Answer: C
Objective: 18.3
Global Outcomes: GO2
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36) 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
Objective: 18.3
Global Outcomes: GO2
37) Cyclic compounds that contain a nitrogen atom are called
A) carbocyclic compounds.
B) aromatic compounds.
C) heterocyclic compounds.
D) homocyclic compounds.
Answer: C
Objective: 18.3
Global Outcomes: GO2
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38) The amide formed in the reaction of benzoic acid and ethylamine is
A)
B)
C)
D)
E)
Answer: B
Objective: 18.4
Global Outcomes: GO2
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39) 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
Objective: 18.4
Global Outcomes: GO2
40) What is the major functional group in the following compound?
O
CH3 - C - NH - CH3
A) ketone
B) carboxylic acid
C) ester
D) amine
E) amide
Answer: E
Objective: 18.4
Global Outcomes: GO2
41) 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
Objective: 18.4
Global Outcomes: GO2
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42) One name for this compound is
O
CH3 - CH2 - C - NH - CH2 - CH3
A) N-ethylpropanamide.
B) N-ethylacetamide.
C) pentanamide.
D) N,N-diethylacetamide.
E) ethylpropionamide.
Answer: A
Objective: 18.4
Global Outcomes: GO2
43) 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
Objective: 18.4
Global Outcomes: GO2
44) 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
Objective: 18.4
Global Outcomes: GO2
45) Which chemical class does phenobarbital belong to?
A) ester
B) amine
C) amide
D) alkane
E) ether
Answer: C
Objective: 18.4
Global Outcomes: GO7
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46) Amides are derivatives of ________ and ________.
A) amines; esters
B) amines; carboxylic acids
C) alkanes; amines
D) carboxylic acids; alcohols
E) alcohols; carboxylic acids
Answer: B
Objective: 18.4
Global Outcomes: GO2
47) What kind of compound is urea?
A) ester
B) acid
C) amide
D) ketone
E) amine
Answer: C
Objective: 18.4
Global Outcomes: GO2
48) 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
Objective: 18.4
Global Outcomes: GO2
49) Amides having fewer than ________ carbons are generally water soluble.
A) five
B) six
C) ten
D) eleven
E) twelve
Answer: B
Objective: 18.4
Global Outcomes: GO2
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50) Which of the following is the reaction for the acid hydrolysis of N-methylacetamide?
A)
O
O
CH3 - C - NH - CH3 + H2O
→ CH3 - C - NH2 + CH3OH
B) O
O
H C - NH - CH3 + H2O
C)
→
H C - NH2 + CH3OH
O
O
CH3 - C - NH - CH3 + H2O + HCl
D)O
O
H C - NH - CH3 + H2O + HCl
E)
→ CH3 - C - NH3+Cl- + CH3OH
→
O
H C - NH3+Cl- + CH3OH
O
CH3 - C - NH - CH3 + H2O + HCl
→ CH3 - C OH + CH3NH3+Cl-
Answer: E
Objective: 18.5
Global Outcomes: GO2
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51) Which of the following is the reaction for the base hydrolysis of N-ethylformamide?
A)O
O
H C - NH - CH2CH3 + NaOH
→
B) O
H C - NH - CH2CH3 + NaOH
O
→
C) O
H C - NH - CH2CH3 + NaOH
H C O-Na+ + CH3CH2 - NH2
O
→
D)O
H C - NH - CH2CH3 + NaOH
H C OH + CH3CH2 - NH2-Na+
H C O-Na+ + NH3 + CH3CH3
O
→
H C O-Na+ + CH3 - NH - CH3
E) O
H C - NH - CH2CH3 + NaOH
→ CH3CH2 - NH2 + NaHCO2
Answer: B
Objective: 18.5
Global Outcomes: GO2
52) 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
Objective: 18.5
Global Outcomes: GO2
53) 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
Objective: 18.5
Global Outcomes: GO2
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54) 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
Objective: 18.6
Global Outcomes: GO7
55) Which of the following is NOT a neurotransmitter?
A) histamine
B) epinephrine
C) glutamate
D) pyridine
E) serotonin
Answer: D
Objective: 18.6
Global Outcomes: GO7
56) A neurotransmitter
A) transmits neurons.
B) transmits neutrons.
C) transmits a nerve impulse.
D) signals loss of appetite.
E) transmits ideas from person to person.
Answer: C
Objective: 18.6
Global Outcomes: GO7
57) 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
Objective: 18.6
Global Outcomes: GO7
58) 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
Objective: 18.6
Global Outcomes: GO7
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18.2 True/False Questions
1) Aniline is the IUPAC approved name for aminobenzene.
Answer: TRUE
Objective: 18.1
Global Outcomes: GO2
2) Aniline is a primary amine.
Answer: TRUE
Objective: 18.1
Global Outcomes: GO2
3) Ethylmethylamine is a tertiary amine.
Answer: FALSE
Objective: 18.1
Global Outcomes: GO2
4) The amine functional group is rarely found in pharmacologically active compounds.
Answer: FALSE
Objective: 18.1
Global Outcomes: GO2
5) Primary amines contain two carbon-containing groups bonded to the nitrogen atom.
Answer: FALSE
Objective: 18.1
Global Outcomes: GO2
6) The compound shown is a tertiary amine.
Answer: TRUE
Objective: 18.1
Global Outcomes: GO2
7) Amines do not form hydrogen bonds.
Answer: FALSE
Objective: 18.2
Global Outcomes: GO2
8) Amines with more that six carbon atoms are soluble in water.
Answer: FALSE
Objective: 18.2
Global Outcomes: GO2
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9) Hydrogen bonds in amines are weaker than those in alcohols.
Answer: TRUE
Objective: 18.2
Global Outcomes: GO2
10) Amines do not ionize in water.
Answer: FALSE
Objective: 18.2
Global Outcomes: GO2
11) Amines act as weak acids by accepting protons from water.
Answer: FALSE
Objective: 18.2
Global Outcomes: GO2
12) Amines are mostly ionized in water.
Answer: FALSE
Objective: 18.2
Global Outcomes: GO2
13) Ammonium salts are usually liquid at room temperature.
Answer: FALSE
Objective: 18.2
Global Outcomes: GO2
14) Ammonium salts are odorless and usually highly water soluble.
Answer: TRUE
Objective: 18.2
Global Outcomes: GO2
15) Crack cocaine is produced by the neutralization and extraction of cocaine from its hydrochloride salt.
Answer: TRUE
Objective: 18.2
Global Outcomes: GO7
16) Quinine is an alkaloid used for treatment of malaria.
Answer: TRUE
Objective: 18.3
Global Outcomes: GO7
17) Heterocyclic amines contain a nitrogen atom in a ring.
Answer: TRUE
Objective: 18.3
Global Outcomes: GO2
18) Caffeine is not an alkaloid.
Answer: FALSE
Objective: 18.3
Global Outcomes: GO2
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19) Atropine and cocaine are used in the diagnosis of eye diseases.
Answer: TRUE
Objective: 18.3
Global Outcomes: GO7
20) Pyrimidine derivatives are found in DNA.
Answer: TRUE
Objective: 18.3
Global Outcomes: GO7
21) Nicotine is a pharmacologically active aromatic amide.
Answer: FALSE
Objective: 18.3
Global Outcomes: GO7
22) Meperidine is a synthetic compound developed from morphine.
Answer: TRUE
Objective: 18.3
Global Outcomes: GO7
23) Urea is one end product of protein metabolism in humans.
Answer: TRUE
Objective: 18.4
Global Outcomes: GO7
24) Aspartame is a sweetener made from corn.
Answer: FALSE
Objective: 18.4
Global Outcomes: GO7
25) The amide group is often found in pharmacologically active substances.
Answer: TRUE
Objective: 18.4
Global Outcomes: GO2
26) Aspirin substitutes may contain amide rather than ester functional groups.
Answer: TRUE
Objective: 18.4
Global Outcomes: GO2
27) When amides are hydrolyzed in basic solution, the products are an ammonium salt and a carboxylic
acid.
Answer: FALSE
Objective: 18.5
Global Outcomes: GO2
28) When amides are hydrolyzed in acidic solution, the products are an amine and a carboxylic acid.
Answer: FALSE
Objective: 18.5
Global Outcomes: GO2
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29) Amphetamines are arylalkylamines with stimulant activity.
Answer: TRUE
Objective: 18.6
Global Outcomes: GO2
30) GABA is not a neurotransmitter.
Answer: FALSE
Objective: 18.6
Global Outcomes: GO2
31) Many important antidepressant drugs are SSRIs.
Answer: TRUE
Objective: 18.6
Global Outcomes: GO2
32) Neurotransmitters are chemicals that transmit a nerve impulse.
Answer: TRUE
Objective: 18.6
Global Outcomes: GO2
33) Nerve poisons bind to acetylcholine esterase enzyme and inhibit its action.
Answer: TRUE
Objective: 18.6
Global Outcomes: GO2
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18.3 Matching Questions
Identify the family for each of the following compounds.
A) amine
B) amide
1) CH3 - CH2 - NH - CH3
Objective: 18.1, 18.4
Global Outcomes: GO2
2)
O
CH3 - CH2 - C - NH - CH3
Objective: 18.1, 18.4
Global Outcomes: GO2
Answers: 1) A 2) B
Select the correct name for the following.
A) N-ethyl formamide
B) dimethylethylamine
C) ethylamide
D) ethyldimethylamine
3) O
H - C - NH - CH2 - CH3
Objective: 18.1, 18.4
Global Outcomes: GO2
4)
CH3
|
CH3 - CH2 - N - CH3
Objective: 18.1, 18.4
Global Outcomes: GO2
Answers: 3) A 4) D
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Classify the amines shown in column 1 as primary, secondary, or tertiary.
A) primary
B) secondary
C) tertiary
5)
CH3
|
CH3 - N - CH3
Objective: 18.1
Global Outcomes: GO2
6) CH3 - CH2 - CH2 - NH2
Objective: 18.1
Global Outcomes: GO2
7)
Objective: 18.1
Global Outcomes: GO2
8)
H
|
CH3 - N - CH2 - CH3
Objective: 18.1
Global Outcomes: GO2
9)
CH3
|
CH3 - CH - CH2 - NH2
Objective: 18.1
Global Outcomes: GO2
Answers: 5) C 6) A 7) A 8) B 9) A
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