Carboxylic Acid and Derivatives

Carboxylic Acid is an organic compound containing a carboxyl functional group. They occur widely in nature and are also synthetically manufactured by humans. Upon deprotonation, carboxylic acids yield a carboxylate anion with the general formula R-COO, which can form a variety of useful salts such as soaps.

Course Contents

  • Carboxylic acids (exemplified by ethanoic acid and benzoic acid)
  • (i) formation from primary alcohols and nitriles
  • (ii) salt, ester and acyl chloride formation
  • Acyl chlorides (exemplified by ethanoyl chloride)
  • (i) ease of hydrolysis compared with alkyl and aryl chlorides
  • (ii) reaction with alcohols, phenols and primary amines
  • Esters (exemplified by ethyl ethanoate and phenyl benzoate)
  • (i) formation from carboxylic acids and from acyl chlorides
  • (ii) hydrolysis (under acidic and under basic conditions)

Learning Outcomes

Candidates should be able to:

  • (a) describe the formation of carboxylic acids from alcohols, aldehydes and nitriles
  • (b) describe the reactions of carboxylic acids in the formation of:
  • (i) salts
  • (ii) esters on condensation with alcohols, using ethyl ethanoate as an example
  • (iii) acyl chlorides, using ethanoyl chloride as an example
  • (iv) primary alcohols, via reduction with lithium aluminium hydride, using ethanol as an example
  • (c) explain the acidity of carboxylic acids and of chlorine-substituted ethanoic acids in terms of their structures
  • (d) describe the hydrolysis of acyl chlorides
  • (e) describe the condensation reactions of acyl chlorides with alcohols, phenols and primary amines
  • (f) explain the relative ease of hydrolysis of acyl chlorides, alkyl chlorides and aryl chlorides
  • (g) describe the formation of esters from the condensation reaction of acyl chlorides, using phenyl benzoate as an example
  • (h) describe the acid and base hydrolysis of esters