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