carboxylic acids

• carboxylic acids can form acyl chlorides during nucleophilic substitution reactions using:

  • PCl5 at rtp
  • PCl3 or SOCl2, heat
• carboxylic acids can be reduced to alcohols using LiAlH4 in dry ether, rtp
• acyl chlorides hydrolyses easily with water to form carboxylic acids
• acyl chlorides can react with alcohols at rtp to form esters in a condensation/nucleophilic acyl substitution reaction
• acyl chlorides can under alkaline hydrolysis to form carboxylate salt

  • using NaOH (aq), rtp
• acyl chlorides can form amides by reacting with amines in a nucleophilic acyl substitution reaction

  • anhydrous conditions needed
  • HCl (g) evolved
• acyl chlorides can react with phenoxide anion to form esters in a condensation reaction
• esters can undergo:

  • acidic hydrolysis, forming carboxylic acids and alcohols
  • alkaline hydrolysis, forming carboxylate salts and alcohols
• esters can be reduced to 2 alcohols using LiAlH4 in dry ether, rtp