Organic Chemistry

618 CHAPTER 15 Aromaticity • Reactions of Benzene

Summary of Reactions

1. Electrophilic aromatic substitution reactions:
   a. Halogenation (Section 15.10)

b. Nitration, sulfonation, and desulfonation (Sections 15.11 and 15.12)

c. Friedel–Crafts acylation and alkylation (Sections 15.13 and 15.14)

d.Formation of benzaldehyde via a Gatterman–Koch reaction (Section 15.13)

e.Alkylation with a Gilman reagent (15.15)

f. Alkylation via a Stille reaction (Section 15.15)

++

Pd(PPh 3 ) 4

THF

Br R

R 4 Sn R 3 SnBr

+

Br R

(R) 2 CuLi ++RCu LiBr

+ + H

CO HCl

high

pressure

AlCl 3 /CuCl

C

O

C

O

R

+ + HCl

1. AlCl 3


2. H 2 O

++RCl HCl

R

O

C

R Cl

AlCl 3

excess

+ HNO 3 + H 2 O

H 2 SO 4

NO 2

+ H 2 SO 4 + H 2 O

SO 3 H

∆

22 + I 2 + 2 H+

HNO 3

I

+ Br 2 + HBr

FeBr 3

Br

Cl

+ Cl 2 + HCl

FeCl 3