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

Alcohols: Oxidation, Dehydration and Nucleophilic Substitution

Students will identify alcohols as a functional group, describe their general properties, and explore their common uses.

Key Questions

  1. Predict the products of oxidising primary, secondary, and tertiary alcohols under controlled versus excess acidified dichromate conditions, drawing full structural formulae and explaining why tertiary alcohols resist oxidation.
  2. Construct a full mechanism for the acid-catalysed dehydration of a secondary alcohol, identifying the carbocation intermediate and predicting the major alkene product using Zaitsev's rule.
  3. Compare the reactivity of alcohols, acyl chlorides, and carboxylic acids towards nucleophilic substitution reactions with the same nucleophile, explaining differences in terms of leaving-group ability and carbonyl electrophilicity.

MOE Syllabus Outcomes

MOE: Alcohols (Basic) - MSMOE: Functional Groups (Introduction) - MS
Level: JC 2
Subject: Chemistry
Unit: Organic Mechanisms: Nucleophilic Substitution, Elimination and Electrophilic Addition
Period: Semester 2

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