1. PROBLEMS CH 18

2. Learning Check
Give the common and IUPAC names, and classify each as primary,
secondary, or tertiary. 2 2

3. 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.
STEP 2 Number the carbon chain to show the position of
STEP 2 the amine group and any substituents.
Propanamine
CH3—CH2 —CH2—NH2
Propylamine (common), 1°
1-Propanamine (IUPAC) 3 3

4. 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.
STEP 2 Number the carbon chain to show the position of
STEP 2 the amine group and any substituents.
ethanamine 4 4

5. 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 5

6. Learning Check Draw the condensed structural formula for each of
the following:
A. 2-pentanamine
B. N-methyl-1-butanamine 6 6

7. 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 7 7

8. Learning Check
Give the common and IUPAC names for each of the following: A. B. C. 8 8

9. Solution A. B. C. Ethylmethylamine(common); N-methylethanamine
Butylethylmethylamine (common);
N-ethyl-N-methyl-1-butanamine
Aniline C. 9 9

10. 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. 10 10

11. 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? 11 11

12. 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?
B. Which compound(s) is/are soluble in water? 12 12

13. Learning Check Identify the following heterocyclic amines: A. B. C. 13

14. Solution Identify the following heterocyclic amines: A. B. C.
Piperidine Pyrrolidine Pyrrole 14 14

15. Learning Check
Identify the heterocyclic amine in serotonin. 15 15

16. Solution
The heterocyclic amine in serotonin is pyrrole. 16 16

17. 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 17 17

18. Examples of IUPAC and Common Names
N-Methylethanamide (IUPAC)
N-Methylacetamide (common)
N-Ethylpropanamide (IUPAC)
N-Ethylpropionamide (common)
CH3—C H2—C—N—CH2—CH3 O ║ H — 18 18

19. Learning Check Write the IUPAC name for the following:
CH3—CH2—CH2—CH2—C—N—CH2—CH3 O ║
CH2—CH3 │ 19 19

20. N,N-diethylpentanamide
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 20 20

21. Learning Check
Draw the condensed structural formulas of the following amides.
A. pentanamide
B. N-methylbutyramide 21 21

22. Solution
Draw the condensed structural formulas of the following amides.
A. pentanamide
B. N-methylbutyramide 22 22

23. Learning Check Give the common and IUPAC names for the following
amides, and classify them as primary, secondary, or tertiary. A. B. 23 23

24. Solution Give the common and IUPAC names for the following
amides, and classify them as primary, secondary, or tertiary. A. B.
Butryamide (common)
butanamide (IUPAC)
primary (1)
N-Ethyl-N-methylacetamide (common) (3)
N-ethyl-N-methylethanamide (IUPAC), tertiary 24 24