CARBOXYLIC ACID RXNS II Chemistry Specialist: Alicia Hart

UC Davis - SASC
e) Alcohol Synthesis - Reduction
O

NaBH4
EtOH
NR
R OH

1. LiAlH 4, Et2O
2. H+, H2O R OH

- NaBH4 is not strong enough to reduce COOH to OH

f) Bromination: Hell-Volhardt-Zelinsky Rxn

O O O

Br2 R
R R
P (trace)
OH OH Br

Br
MECHANISM
Step 1: Acyl Bromide Synth OPBr3
PBr2 PBr2
Br H
O P Br O O O
Br R
R R R
OH OH OH Br
Br
Br
O since Ptrace we continue on to...

R
Br
HOPBr3

Step 2: alpha bromination

H
O OH OH
O
H OP(OH)2 tautomerization
R R R
R Br Br
Br Br Br Br
H

H O
Br O OH OH OH OH
R
HO
R R R R R
(another equiv. of starting material)
Br Br O O
Br Br Br
Br
H H
O OH O O
R R
O OH Br
Br
Br Br