CARBOXYLIC ACID SYNTHESIS

a) Oxidation
i) 1° OH
O

Jones
R OH R OH
(Jones = CrO3, H2SO4, H2O)
* can use a variety of oxidants to get COOH (e.g. KMnO4, Tollen's, Fehling's, etc.)
remember: 2° OH goes to ketone not carbox. acid, and NR with 3°OH

ii) Aldehyde

O O
Jones
(or other strong ox. agent)
H R OH

b) Carbonation
O
1. Mg (or Li), Ether
RH2C X
2. CO2
3. H3O+ R OH

Stepwise: #1 makes grignard reagent (RMgX), #2 makes carboxylate ion, #3 protonates carboxylate

c) Nitrile Hydrolysis
O
1. NaCN
RH2C X
2. H+, H2O,
or R OH
2. NaOH, H2O,
3. H3O+
*without heat stops at amide

d) Oxidation of Aromatic Compounds O

1. KMnO4, H2O,
OH
2. H3O+

needs at least 1H at benzylic position