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Chapter 20: Carboxylic Acids

Start with: Use: Product: Notes

1o alcohol/aldehyde H2CrO4 or KMnO4 carboxylic acid

alkylbenzene H2CrO4 or KMnO4 carboxylic acids

alkene KMnO4
Oxidative Cleavage
KMnO4 or
alkyne carboxylic acids
1) O3 2) S(CH3)2
1) NaCN/acetone nitrile intermediate (formed
Nitriles alkyl halide + carboxylic acid
2) H , H2O then hydrolyzed)

Grignard Addition Grignard reagent CO2 carboxylic acid

Salt Formation carboxylic acid strong base salt + H2O equilibrium reaction

Conversion to Ester carboxylic acid R-OH, H+ ester equilibrium reaction

Conversion to
carboxylic acid amine, heat amide imine salt intermediate
Conversion to
carboxylic acid acid chloride anhydride (+ HCl)
use BH3THF to selectively
carboxylic acid 1) LiAlH4 2) H3O+ 1o alcohol
Reduction reduce a carboxyl group

carboxylic acid LiA(O(CH3)3)3H aldehyde

Chapter 20: Carboxylic Acids

Alkylation carboxylic acid 2 Li-R ketone

Conversion to Acid
carboxylic acid SOCl2 acid chloride