PROBLEMS CH 18
Learning Check
Give the common and IUPAC names, and classify each as primary,
secondary, or tertiary.
2
Solution
A.
STEP 1 Name the longest carbon chain bonded to the N
STEP 1 atoms as alkanamines by replacing e of the
STEP 1 alkane name with amine.
Propanamine
STEP 2 Number the carbon chain to show the position of
STEP 2 the amine group and any substituents.
CH3—CH2 —CH2—NH2
3
2
1
Propylamine (common), 1°
1-Propanamine (IUPAC)
3
Solution (continued)
B.
STEP 1 Name the longest carbon chain bonded to the N
STEP 1 atoms as alkanamines by replacing e of the
STEP 1 alkane name with amine.
ethanamine
STEP 2 Number the carbon chain to show the position of
STEP 2 the amine group and any substituents.
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Solution (continued)
B.
STEP 3 In a secondary or tertiary amine, use the prefix
STEP 3 N- to name groups attached to the N atom.
Ethyldimethylamine (common),
N,N-Dimethylethanamine (IUPAC), 3°
5
Learning Check
Draw the condensed structural formula for each of
the following:
A. 2-pentanamine
B. N-methyl-1-butanamine
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Solution
Draw the condensed structural formula for each of
the following:
A. 2-pentanamine
B. N-methyl-1-butanamine
CH3—CH2—CH2—CH2—NH—CH3
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Learning Check
Give the common and IUPAC names for each of the following:
A.
B.
NH2
C.
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Solution
Ethylmethylamine(common);
N-methylethanamine
A.
B.
Butylethylmethylamine (common);
N-ethyl-N-methyl-1-butanamine
NH2
C.
Aniline
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Classification of Amines
Amines are classified as primary, secondary, or tertiary.

In a primary (1) amine, one carbon group is bonded to the nitrogen
atom.

A secondary (2) amine has two carbon groups.

A tertiary (3) amine has three carbon groups.
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Learning Check
Consider the following compounds:
1) CH3—CH2—CH2—NH2
2) CH3—CH2—NH—CH3
3) CH3—CH2—CH2—CH3
A. Which compound has the highest boiling point?
B. Which compound(s) is/are soluble in water?
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Solution
Consider the following compounds:
1) CH3—CH2—CH2—NH2
2) CH3—CH2—NH—CH3
3) CH3—CH2—CH2—CH3
A. Which compound has the highest boiling point?
1) CH3—CH2—CH2—NH2
B. Which compound(s) is/are soluble in water?
1) CH3—CH2—CH2—NH2
2) CH3—CH2—NH—CH3
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Learning Check
Identify the following heterocyclic amines:
A.
B.
C.
N
N
N
H
H
H
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Solution
Identify the following heterocyclic amines:
A.
B.
C.
N
N
N
H
H
H
Piperidine
Pyrrolidine
Pyrrole
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Learning Check
Identify the heterocyclic amine in serotonin.
15
Solution
The heterocyclic amine in serotonin is pyrrole.
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IUPAC Names of Amides
Write the IUPAC name for
STEP 1 Determine the alkane name of the carbon chain
in the carboxyl portion and replace e with amide.
butanamide
STEP 2 Name each substituent on the N atom using the
prefix N- and the alkyl name.
N-ethylbutanamide
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Examples of IUPAC and Common
Names
N-Methylethanamide (IUPAC)
N-Methylacetamide (common)
—
O H
║
CH3—C H2—C—N—CH2—CH3
N-Ethylpropanamide (IUPAC)
N-Ethylpropionamide (common)
18
Learning Check
Write the IUPAC name for the following:
O CH2—CH3
║ │
CH3—CH2—CH2—CH2—C—N—CH2—CH3
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Solution
STEP 1 Determine the alkane name of the carbon chain
in the carboxyl portion and replace e with amide.
pentanamide
STEP 2 Name each substituent on the N atom using the
prefix N- and the alkyl name.
N,N-diethylpentanamide
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Learning Check
Draw the condensed structural formulas of the following
amides.
A. pentanamide
B. N-methylbutyramide
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Solution
Draw the condensed structural formulas of the following
amides.
A. pentanamide
B. N-methylbutyramide
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Learning Check
Give the common and IUPAC names for the following
amides, and classify them as primary, secondary, or tertiary.
A.
B.
23
Solution
Give the common and IUPAC names for the following
amides, and classify them as primary, secondary, or tertiary.
A.
Butryamide (common)
butanamide (IUPAC)
primary (1)
B.
N-Ethyl-N-methylacetamide (common) (3)
N-ethyl-N-methylethanamide (IUPAC), tertiary
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