Organic Chemistry

662 CHAPTER 16 Reactions of Substituted Benzenes

4. Formation of an azo compound (Section 16.11)


5. Nucleophilic aromatic substitution reactions (Section 16.13)


6. Nucleophilic substitution via a benzyne intermediate (Section 16.14)


7. Electrophilic aromatic substitution reactions of naphthalene (Section 16.16)

CH 3 CH 3

++CH 3 CCl HCl

1. AlCl 3

OCH 3 OCH 3

CH 3 C O

++Br 2 HBr

Br

O

2. H 2 O

CH 3

NH 3 (liq)

− NH

+ 2

Br NH 2

CH 3

+ + Br −

direct-substitution

product

cine-substitution

product

CH 3

NH 2

NO 2 NO 2

Cl

NO 2

NH 3 Cl −

NO 2

∆

++NH 3 H 2 O

+

NO 2

NH 2

NO 2

HO−

+ CH 3 O− + Br−

Br

NO 2 NO 2

∆

OCH 3

+

OH Cl−

HO N N

NN

+

Key Terms

activating substituent (p. 631)
arenediazonium salt (p. 646)
azo linkage (p. 649)
benzyne intermediate (p. 655)
cine substitution (p. 656)
deactivating substituent (p. 631)
direct substitution (p. 656)
donate electrons by resonance (p. 630)

fused rings (p. 657)

inductive electron donation (p. 630)

inductive electron withdrawal (p. 630)

meta director (p. 635)

nitrosamine (p. 651)

N-nitroso compound (p. 651)

nucleophilic aromatic substitution

(p. 653)

ortho–para director (p. 635)

resonance electron donation (p. 630)

resonance electron withdrawal (p. 630)

Sandmeyer reaction (p. 646)

Schiemann reaction (p. 648)

reaction (p. 654)

withdraw electrons by resonance (p. 631)

SNAr