Chapter 6: Amines and Amides

Organic and Biochemistry

for Today 8th Edition
Seager Solutions Manual

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CHAPTER OUTLINE
16.1 Classification of Amines 16.6 Other Biologically Important
16.2 The Nomenclature of Amines Amines
16.3 Physical Properties of Amines 16.7 The Nomenclature of Amides
16.4 Chemical Properties of Amines 16.8 Physical Properties of Amides
16.5 Amines as Neurotransmitters 16.9 Chemical Properties of Amides

LEARNING OBJECTIVES/ASSESSMENT
When you have completed your study of this chapter, you should be able to:
1. Given structural formulas, classify amines as primary, secondary, or tertiary. (Section 16.1; Exercise
16.4)
2. Assign common and IUPAC names to simple amines. (Section 16.2; Exercises 16.8 and 16.10)
3. Discuss how hydrogen bonding influences the physical properties of amines. (Section 16.3; Exercises
16.16 and 16.18)
4. Recognize and write key reactions for amines. (Section 16.4; Exercise 16.26)
5. Name amines used as neurotransmitters. (Section 16.5; Exercise 16.38)

391
392 Chapter 6
6. Give uses for specific biological amines. (Section 16.6; Exercises 16.40 and 16.44)
7. Assign IUPAC names for amides. (Section 16.7; Exercise 16.46)
8. Show the formation of hydrogen bonds with amides. (Section 16.8; Exercise 16.50)
9. Give the products of acidic and basic hydrolysis of amides. (Section 16.9; Exercise 16.52)

LECTURE HINTS AND SUGGESTIONS

1. Point out that amines are derivatives of ammonia, where some, or all, of the hydrogen-nitrogen
bonds have been replaced with carbon-nitrogen bonds. Show the similarities between the common
names of amines and alcohols. Describe amides as condensation products between amines and
carboxylic acids.
2. Some basic principles of "drug design" may be explained using nitrogen-containing drugs from this
chapter. For example, it is easy to show how many antihistamines have the same spatial arrangement
of polar groups as the natural substance histamine. The action of an antagonist drug can be explained
in terms of competitive binding to a receptor site. Another good example of an antagonist drug is
sulfanilamide which has an interesting historical development. Consult textbooks on medicinal
chemistry for ideas.
3. Barbituric acid derivatives can be used to illustrate many simple principles of pharmacology.
Replacing an oxygen atom with a sulfur atom makes the barbiturate more fat soluble and faster
acting such as in the case of Pentothal. The lack of any physiological activity for the 5-
monosubstituted or parent barbituric acid is attributed to the higher acidity of these compounds
which causes them to pass less readily through the so-called "blood-brain barrier" which is lipid in
nature.

SOLUTIONS FOR THE END OF CHAPTER EXERCISES

CLASSIFICATION OF AMINES (SECTION 16.1)
16.1 Primary amines have one carbon atom bonded to the nitrogen atom.
Secondary amines have two carbon atoms directly bonded to the nitrogen atom.
Tertiary amines have three carbon atoms directly bonded to the nitrogen atom.

16.2 Primary amines have the formula: R NH2

Secondary amines have the formula: R NH

R'
Tertiary amines have the formula: R N R"

R'

16.3 a. c.

tertiary

secondary
 Amines and Amides
393
b. d. CH3
N

tertiary

primary

16.4 a. CH3CH2 NH CH2CH3 c. CH3CH2CH NH2

secondary
CH3
primary
b. d. H

N CH2CH3
N

CH3
tertiary
secondary

16.5 H N CH2CH2CH2CH3 CH3 CH3

H H N CH2CHCH3 H N CHCH2CH3
primary

H H
primary primary
CH3 H N CH2CH2CH3 CH3

H N CCH3 CH3 H N CHCH3

secondary
H CH3 CH3
primary secondary

H N CH2CH3 CH3 N CH2CH3

CH2CH3 CH3
secondary tertiary

16.6 H N CH2CH2CH3 CH3 H N CH2CH3 CH3 N CH3

H H N CHCH3 CH3 CH3

primary secondary tertiary
H
primary

THE NOMENCLATURE OF AMINES (SECTION 16.2)

16.7 a. NH2 c. CH3CH2CH2 N CH3

CH3CHCH3 CH2CH3
394 Chapter 6
isopropylamine ethylmethylpropylamine

b. NH CH2CH3

ethylphenylamine

16.8 a. CH3 NH CHCH3 c. CH3CH2CH2CH2 NH2

butylamine
CH3
isopropylmethylamine

b.

N CH2CH3

CH3
ethylmethylphenylamine

16.9 a. c.

2-aminopropane 1-amino-N-ethylpropane
or 2-propanamine N-ethyl-1-propanamine
b.

2-amino- 2-methylpropane
or 2-methyl-2-propanamine
16.10 a. CH3 c. NH CH3

CH3CH2CHCH2 NH2
1-amino-2-methylbutane
or 2-methyl-1-butanamine 1-amino-N-methylcyclobutane
or N-methylcyclobutanamine
b. NH2

aminocyclobutane
or cyclobutanamine
 Amines and Amides
395
16.11 a. b.

N-isopropylaniline

N-ethyl-N-methylaniline

16.12 a. NH CH2CH2CH3 b.

N CH3

CH3
N,N-dimethylaniline

N-propylaniline

16.13 a. CH3 c. NH2

CH3 C NH2

CH3
t-butylamine
or 2-amino-2-methylpropane Cl
or 2-methyl-2-propanamine m-chloroaniline
or 3-chloroaniline
b. CH3CH2 N CH2CH3 d. CH3 NH2

CH3CHCH2CHCH3
4-methyl-2-pentanamine
or 2-amino-4-methylpentane

N,N-diethylaniline or diethylphenylamine
16.14 a. 3-ethyl-2-pentanamine c. N,N-diphenylaniline
NH2 CH2CH3

N
CH3 CH CH CH2CH3

b. m-ethylaniline
NH2

CH2CH3
396 Chapter 6

16.15 a. 2,3-dimethyl-1-butanamine c. N,N-dimethylaniline

NH2 CH3 CH3 CH3 N CH3

CH2 CH CH CH3

b. p-propylaniline

H2N CH2CH2CH3

PHYSICAL PROPERTIES OF AMINES (SECTION 16.3)

16.16 All low molecular weight amines are water soluble because all amines can hydrogen bond
with water. Low molecular weight amines have small aliphatic portions, thus the hydrogen
bonds to water are strong enough to allow the amines to dissolve.

16.17 The boiling points of amines are lower than those the corresponding alcohols because the
hydrogen bonds formed between nitrogen and hydrogen are weaker than the hydrogen
bonds formed between oxygen and hydrogen.

16.18 The boiling points of tertiary amines are lower than the boiling points of primary and
secondary amines because tertiary amines cannot hydrogen bond to each other, while
primary and secondary amines can. The weaker intermolecular forces in tertiary amines
allow them to boil at a lower temperature.

16.19 a. H b. H
O H
CH3CH2 N CH3
H O
H H H
N
CH3CH2 N CH3

16.20 a. H b.
O
N
H
H
CH3CH2 N CH3 H
N

O
H H
 Amines and Amides
397
16.21 CH3 N CH3

(b) CH3 < (a) CH3CH2CH2 NH2 < (c) CH3CH2CH2 OH

Since the molecular weights of these three compounds are comparable, they experience
comparable dispersion forces. The order of their boiling points is determined by the nature of
the other intermolecular forces they experience. Tertiary amines have the lowest boiling point
because they are unable to form hydrogen bonds with other tertiary amines. Primary amines
have an intermediate boiling point because they are capable of forming hydrogen bonds
between their molecules but these hydrogen bonds are not as strong as the hydrogen bonds
between the molecules of primary alcohols, which have the highest boiling point.

16.22 NH CH3 CH3 NH2

CH3

N
CH3

(b) < (c) CH3 < (a) CH3

Since the molecular weights of these three compounds are comparable, they experience
comparable dispersion forces. The order of their boiling points is determined by the nature of
the other intermolecular forces they experience. Tertiary amines have the lowest boiling point
because they are unable to form hydrogen bonds with other tertiary amines. Secondary and
primary amines are both capable of forming hydrogen bonds; however, the nitrogen atom is
more accessible in primary amines. Therefore, secondary amines have an intermediate
boiling point and primary amines have the highest boiling point.

CHEMICAL PROPERTIES OF AMINES (SECTION 16.4)

16.23 CH3—NH2 is a Brønsted base because it can accept a proton from a proton donor. The lone
pair of electrons on the nitrogen atom is available to form a bond to hydrogen ions.

16.24 H

CH3CH2 NH CH2CH3 + H2O CH3CH2 +NH CH2CH3 + OH-

O O

C Cl C NH2

+ NH3 + HCl
16.25 a.
O
b.
H
-O C CH3
N CH3 O
N+ CH3
+ CH3C OH
CH3 CH3
398 Chapter 6
c. O

CH3CH2 N CH3 + CH3 C Cl no reaction

CH3

d.
N H + HCl NH2+Cl-

e.
N H + H2O NH2+ + OH-

f. CH3CH2 NH2+Cl- + NaOH CH3CH2 NH + H2O + NaCl

CH3 CH3

+ -
16.26 a. CH3CH2CH2CH2—NH2 + HCl → CH3CH2CH2CH2—NH3 Cl
b. NH2 NH3+
+ H2O + OH-

c. O

NH 2 NH 3+ -O C CH3
O

+ CH3C OH

d. NH3+Cl- NH2

CH3CHCH3 + NaOH CH3CHCH3 + H2O + NaCl

e. O O

CH3CH C Cl + CH3 NH2 CH3CH C NH + HCl

CH3 CH3 CH3

O
f.
O O C OH

C O C + NH3 +
O

H2N C
 Amines and Amides
399

16.27 The structure of a quaternary ammonium salt differs from the structure of a salt of a tertiary
amine because the nitrogen atom of a quaternary ammonium salt is bonded directly to four
carbon atoms, while the nitrogen atom of a salt of a tertiary amine is bonded directly to three
carbon atoms and one hydrogen atom.

16.28 Amine salts are more soluble in water, and therefore in blood, than their corresponding
amines; consequently, the amine salts are the preferred form for drugs.

16.29 CH3 CH3

N NH+Cl-

+ HCl

CH3O CH3O

16.30

O O CH3 NH CH3 C N CH3

+ + O
CH3 C O C CH3 CH3 CH3
CH3 C OH

16.31 a. O

NH2 NH3+CH3 C O-
O

CH3 C OH
400 Chapter 6
O O
b.

CH3 NH2 C NH CH3 C Cl

c. CH3 CH3
H2O
CH3CH NH2 CH3CH NH3+ + OH-

16.32 a.

NH3+Cl- NH2 NaOH

b. O O
NH3
CH3CH2 C Cl CH3CH2 C NH2
c. CH3 NH CH3 NH2+Cl-
HCl
CH3 CH3

AMINES AS NEUROTRANSMITTERS (SECTION 16.5)

16.33 A neuron consists of a bulbous body called the soma attached to a long stemlike projection
called an axon. Numerous short extensions called dendrites are attached to the large bulbous
end of the soma, and filaments called synaptic terminals are attached to the end of the axon.
A small gap called a synapse exists between the synaptic terminals of the axon and the
dendrites of the next neuron.

16.34 The gap between neurons is called a synapse.

16.35 Two amino acids that are starting materials for the synthesis of neurotransmitters are tyrosine
(produces norepinephrine) and tryptophan (produces serotonin).

16.36 The two amines often associated with the biochemical theory of mental illness are
norepinephrine and serotonin.

16.37 During nerve impulse transmission, neurotransmitters carry the nerve impulses from one
nerve cell to another.

16.38 Four neurotransmitters important in the central nervous system are acetylcholine,
norepinephrine, dopamine, and serotonin.
OTHER BIOLOGICALLY IMPORTANT AMINES (SECTION 16.6)
16.39 Epinephrine is the fight-or-flight hormone because it is released in response to pain, anger, or
fear and provides glucose for a sudden burst of energy.

16.40 The clinical uses of epinephrine are as a component of injectable local anesthetics as well as to
reduce hemorrhage, treat asthma attacks, and combat anaphylactic shock.
 Amines and Amides
401
16.41 The physiological effects of amphetamines on the body include raising the glucose level in the
blood and increasing pulse rate and blood pressure. Abuse of amphetamines can cause long
periods of sleeplessness, weight loss, and paranoia.

16.42 Alkaloids are derived from plants.

16.43 Alkaloids are weakly basic because they are amines and amines are weakly basic.

16.44 a. found in cola drinks caffeine

b. used to reduce saliva flow during surgery atropine
c. present in tobacco nicotine
d. a cough suppressant codeine
e. used to treat malaria quinine
f. an effective painkiller morphine

THE NOMENCLATURE OF AMIDES (SECTION 16.7)

16.45 a. c.

2-ethylbutanamide
N-isopropylbenzamide
b. d. O

CH3CH2 C N CH3

CH3
N-phenylbutanamide
N,N-dimethylpropanamide

16.46 a. O b. O

CH3CH2CH2 C NH CH3 CH3 C N CH3

N-methylbutanamide
CH3
N,N-dimethylethanamide
c. O d. O

C NH2 CH3CH2CH C NH2

CH3
2-methylbutanamide
CH3
o-methylbenzamide or
2-methylbenzamide

16.47 a. benzamide c. N-methyl-3-phenylbutanamide

402 Chapter 6

b. N-methylethanamide

16.48 a. propanamide c. N,N-dimethylmethanamide

O O

CH3CH2 C NH2 H C N CH3

b. N-ethylpentanamide
O CH3

CH3CH2CH2CH2 C NH CH2CH3

PHYSICAL PROPERTIES OF AMIDES (SECTION 16.8)

16.49 a. H b. O
O
H H N C CH3
H O
O H
O H

CH3 C N H
CH3 C N CH3

H
CH3
16.50 a. H
b. O
O
H H N C CHCH3
H O

O H CH3
O H H

C N H O CH3CH C N H

H H
CH3 H

O
H H

16.51 The boiling points of disubstituted amides are often lower than those of unsubstituted amides
because the disubstituted amides are unable to form hydrogen bonds between their
molecules, while the unsubstituted amides are able to form such hydrogen bonds.

CHEMICAL PROPERTIES OF AMIDES (SECTION 16.9)

 Amines and Amides
403
16.52 a. O O

CH3 C NH CH2CH3 + NaOH heat CH3 C O-Na+ + NH2 CH2CH3

b. O O

heat
CH3CH2 C NH2 + H2O + HCl CH3CH2 C OH + NH4+Cl-

16.53 a.

b.

16.54 O O

heat
C N CH2CH3 + NaOH C O-Na+

CH2CH3 + H N CH2CH3
CH3 CH3
CH2CH3

CH3
16.55
O

heat
CH3CH2 N CH2 C NH + H2O + 2 HCl
CH3
CH2CH3 H O
CH3 Cl-
CH3CH2 N+ CH2 C OH + Cl-NH3+

CH2CH3

CH3
ADDITIONAL EXERCISES
16.56 a. C4H11N is a saturated amine (butanamine, 2-butanamine, 2-methyl-1-propanamine,
2-methyl-2-propanamine, or diethylamine).
b. C5H12N2 is an unsaturated amine with one carbon-carbon double bond.
c. C4H7N is an unsaturated amine with two carbon-carbon double bonds.

16.57 0.216 g a min e

= 131 mole
g

16.50 mL HCl ( 0.100 mole HCl

1000 mL HCl )( 1 mole a min e
1 mole HCl )
404 Chapter 6

16.58 The hydrolysis of nylon 66 with NaOH would produce a sodium dicarboxylate salt and a
diamine as shown below:
O O O O

C(CH2)4CNH(CH2)6NH + n NaOH n Na+-O C(CH2)4C O-Na+

n +
n NH2(CH2)6NH2

16.59 Alkaloids in plants frequently occur as their salts, which are ionic. Initial treatment with a
base neutralizes these salts and converts the alkaloids to their neutral form, making them
more soluble in a nonpolar organic solvent.

16.60 O
+
O CH3
CH3 C OH
CH3 C O CH2CH2 N CH3 + H2O +
CH3 +
CH3
HO CH2CH2 N CH3

CH3

ALLIED HEALTH EXAM CONNECTION

16.61 A neurotransmitter is a substance that acts as a chemical bridge in nerve impulse transmission
between nerve cells.

16.62 Primary amines have the formula: R NH2

Secondary amines have the formula: R NH

R'
Tertiary amines have the formula: R N R"

R'

16.63 The stimulant in coffee is (d) caffeine.

16.64 The most likely products of a reaction between CH3CH2NH2 and H2O are (a) CH3CH2NH3
+

-
and OH .

CHEMISTRY FOR THOUGHT

16.65 It might be more practical for chemical suppliers to ship amines as amine salts because amine
salts are solids, while amines are often liquids. It is easier to ship a solid than a liquid.
 Amines and Amides
405
16.66 O O

NH2(CH2)4NH2 Cl C(CH2)2C Cl
4 carbon diamine 4 carbon diacid chloride

16.67 It might be dangerous on a camping trip to prepare a salad using an unknown plant because
the plant could contain dangerous chemicals, which could be toxic or physiologically
dangerous.

16.68 The ending of the word maleate is “-ate,” which indicates that this compound is a salt or ester
of maleic acid.
O
16.69
CH3CH2 OH CH3 NH3+CH3 C O-
O

CH3CH2 OH + (O) CH3C H + H2O

O O

CH3C H + (O) CH3C OH

O O

CH3C OH + CH3 NH2 CH3 NH3+CH3 C O-

16.70 Hydrochloric acid is used to prepare an amine hydrochloride salt.

16.71 DNA and RNA contain components called bases because the components are amines.

16.72 A catalyst can be used to hydrolyze amides under milder conditions than strong acids or
bases and heat.
16.73 Alkaloids can be extracted from plant tissues using dilute hydrochloric acid because the acid
reacts with the amines to produce water soluble amine salts.

EXAM QUESTIONS
MULTIPLE CHOICE
1. Which compound is a secondary amine?
a. (CH3)2NCH2CH3 c. CH2CH(NH2)CH3
b. NH2CH2CH3 d. CH3NHCH3
Answer: D
CH3 CH CH2 CH3

2. The amine NH2 is a _____ amine.

a. primary b. secondary c. tertiary d. quaternary
Answer: A
 406 Chapter 6
H

3. The amine is:

a. primary. b. secondary. c. tertiary. d. quaternary.
Answer: B
NH2

CH3

4. What is the correct IUPAC name for the following compound?

a. N-methylaniline c. 1-methylaniline
b. 2-methylaniline d. 1-methyl-2-aniline
Answer: B

5. What is another name for 2-amino-2-methylpropane?

a. 2-aminobutane c. sec-butylamine
b. isobutylamine d. t-butylamine
Answer: D
 Amines and Amides
407
6. Which of the following options gives the correct structure for 3-amino-3-methylpentane?
a. CH3

CH3 CH2 N CH2 CH3

b. CH3

NH

CH3 CH2 CH CH2 CH3

c. CH3

CH3 CH2 C CH2 CH3

NH2

d. CH3

CH2

CH3 CH2 CH CH2 CH2 NH2

Answer: C
NH CH3

7. What is the correct IUPAC name for the following compound?

a. methylaniline c. 1-methylaniline
b. 1-N-methylaniline d. N-methylaniline
Answer: D

8. Which of the following is the correct IUPAC name for the compound,
CH3 CH2 CH CH2 CH CH3

NH2

?
a. 1-amino-2-phenylhexane c. 3-amino-2-phenylhexane
b. 2-amino-4-phenylhexane d. 5-amino-3-phenylhexane
Answer: B
 408 Chapter 6

9. Which of the following is the best representation for hydrogen bonding in methylamine?
a. H H c. H H

CH3 N H CH3 N H CH3 N H N H

CH3

b. H H d. H H

CH3 N H H N CH3 CH3 N N CH3

H H
Answer: C

10. Which amine has the lowest boiling point?

a. CH3 CH2 CH2 NH2 c. CH3 CH2 NH CH3

b. CH3 d. CH3

CH3 N CH3 CH3 CH NH2

Answer: B

11. Which of the following amines can form hydrogen bonds with water?
a. primary and secondary c. all three (primary, secondary and tertiary)
b. just tertiary d. none of the amines
Answer: C

12. Primary amines have boiling points slightly lower than those of _____ with comparable molecular
weights.
a. alcohols b. carboxylic acids c. alkanes d. tertiary alcohols
Answer: A

13. What is a characteristic of amines that is associated with molecular size?

a. The larger amines have an odor like that of decaying fish.
b. The larger amines have a boiling point near room temperature.
c. The solid amines always have a branched chain structure.
d. Strong hydrogen bonding of the tertiary amines explains their boiling points.
Answer: A

14. Amines function chemically as organic:

a. acids. c. salts.
b. bases. d. more than one response is correct
Answer: B
 Amines and Amides
409

15. Some amine drugs are administered in the form of salts in order to:
a. make them form into pills more easily.
b. make them taste better.
c. make them more basic.
d. make them more soluble in body fluids.
Answer: D
CH3

16. What are the products of the reaction CH3 CH NH2 + H2O ?
a. CH3 c. CH3

CH3 CH NH3+ + OH- CH3 CH NH OH + H2

b. CH3 d. CH3

CH3 CH OH + NH3 CH3 C NH2 + H2

OH
Answer: A

17. Acetaminophen is an amide. Which of the following statements about amides is true?
a. The amides are the most acidic in nature of the organic compounds.
b. Amides can be produced by the reaction of a carboxylic acid chloride and ammonia.
c. Amides form the only class of organic compounds that can bond directly to the benzene ring.
d. All of these responses are correct.

Answer: B

18. What organic product will the reaction of CH3-CH2-NH3+ Cl- with aqueous sodium hydroxide
produce?
a. CH3—CH2—NH3+ OH- c. CH3—CH2—NH2
b. CH3—CH2—NH—CH3 d. CH3—CH2—NH—OH
Answer: C

19. Amides are formed as a product of reactions between:

a. carboxylic acid chlorides and alcohols. c. aldehydes and alcohols.
b. carboxylic acid chlorides and amines. d. amines and alcohols.
Answer: B
 410 Chapter 6

20. What is the product of the following reaction?

O

CH3 CH C Cl + CH3 NH CH3

CH3
a. O c. O

CH3 CH C NH CH3 CH3 CH C O N CH3

CH3 CH3 CH3

b. O CH3 d. OH

CH3 CH C N CH3 CH3 CH CH N CH3

CH3 CH3 CH3

Answer: B

21. Which of the following substances act as (a) neurotransmitter(s)?

a. catechol c. norepinephrine
b. dopamine d. more than one response is correct
Answer: D

22. The "fight or flight" hormone is:

a. epinephrine. b. amphetamine. c. serotonin. d. dopamine.
Answer: A

23. A substance which is used to constrict blood vessels in the vicinity where a local anesthetic is injected
is:
a. dopamine. c. epinephrine.
b. serotonin. d. N-methylamphetamine.
Answer: C

24. Amphetamines have structures similar to that of:

a. atropine. b. epinephrine. c. serotonin. d. lidocaine.
Answer: B

25. The alkaloid present in cola drinks is:

a. caffeine. b. nicotine. c. cocaine. d. dopamine.
Answer: A

26. An alkaloid used in treating malaria is:

a. histamine. b. quinine. c. atropine. d. nicotine.
Answer: B

27. An alkaloid used to reduce saliva flow in surgical patients is:

 Amines and Amides
411
a. atropine. b. quinine. c. caffeine. d. codeine.
Answer: A

28. An alkaloid present in some cough syrups is:

a. morphine. b. cocaine. c. codeine. d. methadone.
Answer: C
O

29. What is the IUPAC name for the following compound? CH3 CH2 C NH CH3
a. N-methylpropionamide c. 1-methylpropanamide
b. N-methylpropanamide d. 2-butanamide
Answer: B

30. What is the structure of 2-ethylbenzamide?

a. O c. O

C NH2 NH CH

CH2 CH3

CH2 CH3
b. O d. O

C NH CH2 CH3 C NH2

CH2 CH3
Answer: A
O

CH3 CH2 C N CH2CH3

31. What is the IUPAC name for the compound? CH3

a. 1-ethyl-2-methylpropanamide c. N-ethyl-N-methylpropanamide
b. 1-ethylmethylpropanamide d. N-ethylmethylpropanamide
Answer: C
 412 Chapter 6

32. Which of these amides has the lowest melting point?

a. O CH3 c. O

CH3 C N CH3 CH3 CH2 CH2 C NH CH3

b. O d. O

CH3 CH2 C NH CH3 CH3 CH C NH CH3

CH3
Answer: A

33. Which of the following four-carbon amides would be the least soluble in water?
a. simple amides c. disubstituted amides
b. monosubstituted amides d. all would be equally soluble
Answer: C

34. Which of the following correctly shows hydrogen bonding between amide molecules?
O O O O
a. c.
CH3 C N H H N C CH3 CH3 C N H CH3 C N H

H H H H

b. O d. CH3
O
CH3 C N H O
CH3 C N H C O
H CH3 C N H
H H N
H
H
Answer: B

35. What are the products of the following hydrolysis?

O

CH3 CH2 C NH CH3 + H2O + HCl

a. O c. O

CH3 CH2 C OH + CH3NH3+Cl- CH3 CH2 C NH2 + CH3Cl

b. O d. O

CH3 CH2 C O- + CH3NH3+ CH3 CH2 C OH + CH3NH2

Answer: A
 Amines and Amides
413

36. What are the products of the following reaction?

O

CH3 CH2 C NH CH2CH3 + NaOH

a. O

CH3 CH2 C OH + CH3CH2NH2

b. CH3CH2CH2OH + CH3CH2NH2 + Na+
c. O

CH3 CH2 C O-Na+ + CH3CH2NH3+Cl-

d. O

CH3 CH2 C O-Na+ + CH3CH2NH2

Answer: D

37. Hydrolysis of an amide under basic conditions produces:

a. a carboxylic acid and amine. c. a carboxylic acid and amine salt.
b. a carboxylate salt and amine salt. d. a carboxylate salt and amine.
Answer: D

38. Which compound is a tertiary amine?

a. CH3 c. NH2

CH3 N CH2 CH3 CH3 CH CH3

b. NH2 CH2 CH3 d. O

HC NH CH3
Answer: A

39. Which of the following in not an important neurotransmitter in the central nervous system?
a. dopamine b. tryptophan c. serotonin d. norepinephrine
Answer: B

40. What product will form in the reaction of an amine with water (H2O)?
a. an ammonium ion and OH- c. an amide plus HCl
b. a salt d. an amide plus a carboxylic acid
Answer: A

41. What product will form in the reaction of an amine with HCl?
a. an ammonium ion and OH- c. an amide plus HCl
b. an amine salt d. an amide plus a carboxylic acid
Answer: B

42. What product will form in the reaction of an amine with an acid chloride?
a. an ammonium ion and OH- c. an amide plus HCl
 414 Chapter 6
b. a salt d. an amide plus a carboxylic acid
Answer: C

43. What product will form in the reaction of an amine with an acid anhydride?
a. an ammonium ion and OH- c. an amide plus HCl
b. a salt d. an amide plus a carboxylic acid
Answer: D

44. Nylon, a polyamide, forms from the reaction of a diacid chloride and a________.
a. amide c. diamide
b. amine d. diamine
Answer: D

45. Proteins are polymers produced by linking together amino acids, where the amino group of one will
react with the acid group of another. What type of functional group is produced?
a. anhydride b. secondary amine c. amide d. ether
Answer: C

TRUE-FALSE
1. Nitrogen-containing functional groups in medications are more common than other functional groups.
Answer: T

2. Aniline is the starting block for many of the aromatic amines.

Answer: T

3. A tertiary amine is one that has one hydrogen bound to the nitrogen.
Answer: F

4. 1-amino-2-methylpropane is a secondary amine.

Answer: F

5. t-Butylamine is a tertiary amine.

Answer: F

6. Amine hydrochlorides are usually more soluble than the amine in water.
Answer: T

7. Morphine is an alkaloid.
Answer: T

8. Amines react readily with tertiary amines to form amides.

Answer: F

9. Amines are less basic than amides.

Answer: F

10. Putrescine is an amine of relatively low molecular weight that has a terrible odor.
Answer: T
 Amines and Amides
415
11. The amines are very common organic compounds that behave as bases.
Answer: T
12. Acid anhydrides and acid chlorides will react with amines to form amides.
Answer: T

13. Amine salts are ionic compounds.

Answer: T

14. Amine salts tend to be less soluble than their corresponding aminex.
Answer: F

15. Some of the amines have the ability to act as disinfectants. The way in which Zephiran chloride
works is to draw the moisture out of the cytoplasm of bacteria.
Answer: F

16. Morphine sulfate is used as an anesthetic in preference to morphine.

Answer: T

17. The reason that amides are produced from acid chlorides is that the acid-amine reaction usually
yields a salt, not an amide.
Answer: T

18. The major reason that acetaminophen dissolved in water is used instead of aspirin is that it is more
effective than aspirin.
Answer: F

19. Basic hydrolysis of an amines yields an ammonium salt.

Answer: T

20. The molecules that serve as neurotransmitters are complex amides.

Answer: F