Organic Chemistry

Problems 915

b.Pyridine (Section 21.10):

7. Nucleophilic aromatic substitution reactions of pyridine (Section 21.10).

NNCl NH 2

N

+

+ −NH 2 +

+

N

Cl

N

N

NH 2

Cl−

Cl−

N

++Br−

Br

N

NH 2

−NH

2

−NH

2

∆

∆

∆

Br

+ Br 2

N

+ HBr

FeBr 3

300 °C

N

+

+

Br 2

N

FeBr 3

90 °C

N

O−

+

O−

Br

PCl 3

N

Br

Key Terms

alkaloid (p. 884)
amine inversion (p. 885)
amines (p. 883)
Cope elimination reaction (p. 894)
exhaustive methylation (p. 891)
furan (p. 897)
heteroatom (p. 884)
heterocycle (p. 884)
heterocyclic compound (p. 884)

Hofmann elimination reaction (p. 889)

imidazole (p. 907)

iron protoporphyrin IX (p. 909)

ligation (p. 909)

natural product (p. 884)

phase transfer catalysis (p. 893)

phase transfer catalyst (p. 893)

porphyrin ring system (p. 909)

protoporphyrin IX (p. 909)

purine (p. 909)

pyridine (p. 902)

pyrimidine (p. 909)

pyrrole (p. 897)

quaternary ammonium ion (p. 889)

reductive amination (p. 896)

thiophene (p. 897)

Problems

28. Name the following compounds:

a. b. c. d.

29. Give the product of each of the following reactions:

a. c. e.

b. d. f.

NH 2

+ CH 3 CH 2 CH 2 Br

O CH^3

+ CH 3 CCl

O

N Br

+ HO−

N Cl

1. C N C 6 H 5 Li


2. H 2 /Pd

CH 3 CH 2 CH 2 CH 2 Br

−

C

+ Cl

O

N

H

CH 3

CH 3 CH 2 N

H

Cl

N

H H

N

CH 3

CH CH^3

3

NH

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