chem 239 carboxylic acids + derivatives

write the diagram for carboxylic acid & its derivatives with reagents

carboxylic acid to acyl chloride

carboxylic acid to anhydride

carboxylic acid to ester

carboxylic acid derivative to amide

carboxylic acid derivative + NH3 = amide

• acid chloride

• ester

• anhydride

amide to nitrile

breakdown of carboxylic acid derivatives

• H2O, pyridine

• EtOH, pyridine

• MeNH2, pyridine

• XS LAH, H2O

• XS MeMgBr, H2O

• Al(OtBu)3H, H2O

• Et2CuLi, H2O

• H2O, pyridine = carboxylic acid

• EtOH, pyridine = ether

• MeNH2, pyridine = amide

• XS LAH, H2O = primary alcohol

• XS MeMgBr, H2O = tertiary alcohol

• Al(OtBu)3H, H2O = aldehyde

• Et2CuLi, H2O = ketone

breakdown of nitriles

nitrile + H3O+ + H2O = carboxylic acid

nitrile + EtMgBr + H3O+ = ketone