Chapter 20: Carboxylic Acids

Start with:
1o alcohol/aldehyde alkylbenzene alkene Oxidative Cleavage alkyne Nitriles Grignard Addition Salt Formation Conversion to Ester Conversion to Amide Conversion to Anhydride alkyl halide Grignard reagent carboxylic acid carboxylic acid carboxylic acid carboxylic acid carboxylic acid carboxylic acid

Use:
H2CrO4 or KMnO4 H2CrO4 or KMnO4 KMnO4 KMnO4 or 1) O3 2) S(CH3)2 1) NaCN/acetone 2) H , H2O CO2 strong base R-OH, H+ amine, heat acid chloride 1) LiAlH4 2) H3O+ LiA(O(CH3)3)3H
+

Product:
carboxylic acid carboxylic acids ketones/carboxylic acids carboxylic acids carboxylic acid carboxylic acid salt + H2O ester amide anhydride (+ HCl) 1o alcohol aldehyde

Notes

Oxidation

nitrile intermediate (formed then hydrolyzed)

equilibrium reaction equilibrium reaction imine salt intermediate

use BH3THF to selectively reduce a carboxyl group

Reduction

Chapter 20: Carboxylic Acids
Alkylation Conversion to Acid Chloride carboxylic acid carboxylic acid 2 Li-R SOCl2 ketone acid chloride