ester/acyl chloride

• ester to carboxylic acid

  • dilute acid
  • heat
• ester to carboxylate

  • NaOH (aq), alkaline hydrolysis
  • OH-, heat
• ester to carboxylic acid

  • dilute acid
  • heat
• acyl chloride to carboxylic acid

  • H2O
• acyl chloride to ester

  • alcohol
• acyl chloride to primary amide

  • NH3
• acyl chloride to secondary amide

  • primary amide
• esters can form

  • carboxylic acids
  • carboxylates
• esters are formed by

  • carboxylic acids + alcohol
  • acyl chloride + alcohol
• acyl chloride can form

  • primary and secondary amides
  • carboxylic acids
  • esters
• acyl chloride can be formed by carboxylic acid
• carboxylic acid + alcohol -> ester +water

  • heat
  • conc H2SO4
• acid anhydride + alcohol -> ester + carboxylic acid

  • heat
• carboxylic acid + alcohol -> ester + water

  • conc H2SO4 catalyst
  • heat
• general equation of esterification

  • RCOOH + ROH -> RCOOR + H2O
• an acid anhydride is 2 carboxylic acids joined together by a loss of a water molecule
• better yield of ester using acyl chloride because its not reversible