Unformatted text preview: CHZR CHR2 COOH
H20 H2804, heat
CR3 (3 when R is not H does not react
c) Reductions: 1. Nitroarenes (read pag 962) Nitro group can be reduced to primary amines- One method is
reduction with Sn or Fe in HCI. COCH3 COCH3
1. Sn, HCi
2. NaOH NH2
m— Nitroacetophenone m— Aminoacetophenone 2. Aryl ketones .(read Ch 12.8) Carbonyl group can be reduced to an alkyl group.
Clemmensen reduction uses Zn(Hg) amalgam in cone. HCl Ex:
‘ 2“ (”9) “K.
O ........... M ..... a g
Acetophenone Ethyibenzene Wolff-Kishner reduction uses hydrazine (HzN-NHz) and sodium or potassium hydroxide and
COCH3 CHZCHa 1. HZNNHZ,
© 2 KOH d) Nucleophilic substitution in benzilic halides (read 11.14) Primary benzylic halides are very good substrates for 8N2 reactions.
Example: CHzcl CHZOCOCH3 CH3C02 Na
acetic acid + NaCi p—Nitrobenzyi acetate For secondary and tertiary benzylic halide, elimination is a competitive reaction.
The extra stability of benzylic cation is due to delocalization of positive charge into the ring. ...
View Full Document
- Summer '08
- Organic chemistry