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Organic Mechanisms: Nucleophilic Substitution, Elimination and Electrophilic Addition · Semester 2

Carboxylic Acids, Acyl Chlorides and Ester Hydrolysis Mechanisms

Students will identify carboxylic acids and esters, understand their basic properties, and learn about the formation of esters (esterification).

Key Questions

  1. Draw the mechanism for acid-catalysed esterification and compare the reactivity of acyl chlorides versus carboxylic acids with alcohols and amines, explaining the rate difference in terms of leaving-group ability.
  2. Analyse the products and mechanisms of acid hydrolysis versus base hydrolysis (saponification) of an ester, explaining why base hydrolysis is irreversible and therefore driven quantitatively to completion.
  3. Evaluate the relative acidity of carboxylic acids, phenols, and alcohols using Ka data, explaining enhanced acidity in substituted carboxylic acids through inductive effects and resonance stabilisation of the carboxylate anion.

MOE Syllabus Outcomes

MOE: Carboxylic Acids (Basic) - MSMOE: Esters (Basic) - MS
Level: JC 2
Subject: Chemistry
Unit: Organic Mechanisms: Nucleophilic Substitution, Elimination and Electrophilic Addition
Period: Semester 2

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