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PROBLEMS CH 18
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Learning CheckGive the common and IUPAC names, and classify each as primary,secondary, or tertiary.
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SolutionA.
STEP 1 Name the longest carbon chain bonded to the NSTEP 1 atoms as alkanamines by replacing e of theSTEP 1 alkane name with amine.
STEP 2 Number the carbon chain to show the position ofSTEP 2 the amine group and any substituents.
CH3—CH2 —CH2—NH2
Propylamine (common), 1°
1-Propanamine (IUPAC)
3 2 1
Propanamine
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Solution (continued)
ethanamine
B.
STEP 1 Name the longest carbon chain bonded to the NSTEP 1 atoms as alkanamines by replacing e of theSTEP 1 alkane name with amine.
STEP 2 Number the carbon chain to show the position ofSTEP 2 the amine group and any substituents.
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Solution (continued)B.
STEP 3 In a secondary or tertiary amine, use the prefixSTEP 3 N- to name groups attached to the N atom.
Ethyldimethylamine (common),
N,N-Dimethylethanamine (IUPAC), 3°
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Learning CheckDraw the condensed structural formula for each of the following:
A. 2-pentanamine
B. N-methyl-1-butanamine
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Solution
CH3—CH2—CH2—CH2—NH—CH3
Draw the condensed structural formula for each ofthe following:
A. 2-pentanamine
B. N-methyl-1-butanamine
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Learning Check Give the common and IUPAC names for each of the following:
A.
B.
C.
NH2
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Solution
Ethylmethylamine(common); N-methylethanamine
A.
B.
C.
NH2
Butylethylmethylamine (common);N-ethyl-N-methyl-1-butanamine
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
H
N
H
N
H
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Solution
Identify the following heterocyclic amines: A. B. C.
Piperidine Pyrrolidine Pyrrole
N
H
N
H
N
H
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Learning Check
Identify the heterocyclic amine in serotonin.
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Solution
The heterocyclic amine in serotonin is pyrrole.
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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
IUPAC Names of Amides
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N-Methylethanamide (IUPAC)N-Methylacetamide (common)
N-Ethylpropanamide (IUPAC)N-Ethylpropionamide (common)
18
CH3—C H2—C—N—CH2—CH3
O║
H—
Examples of IUPAC and Common Names
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CH3—CH2—CH2—CH2—C—N—CH2—CH3
O║
CH2—CH3│
Learning Check
Write the IUPAC name for the following:
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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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Solution
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Learning Check
Draw the condensed structural formulas of the following amides.
A. pentanamide
B. N-methylbutyramide
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Draw the condensed structural formulas of the following amides.
A. pentanamide
B. N-methylbutyramide
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Solution
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Give the common and IUPAC names for the followingamides, and classify them as primary, secondary, or tertiary.
A.
B.
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Learning Check
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Give the common and IUPAC names for the followingamides, and classify them as primary, secondary, or tertiary.
A.
B.
24
Butryamide (common)butanamide (IUPAC)primary (1)
N-ethyl-N-methylethanamide (IUPAC), tertiary
N-Ethyl-N-methylacetamide (common) (3)
Solution