Organic Chemistry

g.Alkylation via a Suzuki reaction (Section 15.15)

2. Clemmensen reduction and Wolff–Kishner reduction (Section 15.15)

CR

O

CR

O

Zn(Hg), HCl, ∆

Clemmensen

reduction

CH 2 R

CH 2 R

H 2 NNH 2 , HO−, ∆

Wolff–Kishner

reduction

NaOH

Pd(PPh 3 ) 4

R

O

O

+ B HO

O

O

+ B + NaBr

Br R

Problems 619

aliphatic (p. 594)
annulene (p. 595)
antiaromatic (p. 602)
aromatic (p. 595)
benzyl group (p. 604)
Clemmensen reduction (p. 616)
electrophilic aromatic substitution
reaction (p. 607)

Friedel–Crafts acylation (p. 607)

Friedel–Crafts alkylation (p. 607)

Gatterman–Koch reaction (p. 613)

halogenation (p. 607)

heteroatom (p. 598)

heterocyclic compound (p. 598)

Hückel’s rule, or the rule (p. 595)

nitration (p. 607)

4 n+ 2

phenyl group (p. 604)

principle of microscopic reversibility

(p. 611)

Stille reaction (p. 616)

sulfonation (p. 607)

Suzuki reaction (p. 617)

Wo l ff–Kishner reduction (p. 616)

Problems

25. Which of the following compounds are aromatic? Are any antiaromatic? (Hint:If possible, a ring will be nonplanar to avoid being
    antiaromatic.)


26. Give the product of the reaction of excess benzene with each of the following reagents:

a. c.

b. propene+HF d. dichloromethane+AlCl 3

isobutyl chloride+AlCl 3 neopentyl chloride+AlCl 3

CH 2

N

H

N

N N

N

H

H

N

N

H

NN

H

H

N

N

O

N+

+

CH 2

O

−

+ +

Key Terms