Textbook Question
Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(d) ethyl acetate → 3-methylpentan-3-ol
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22. Carboxylic Acid Derivatives: NAS
Nucleophilic Acyl Substitution
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Determine the major product for the following reaction.
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Verified step by step guidance1
Identify the reactants: The reaction involves an acyl chloride (ethanoyl chloride) and a cyclohexanol in the presence of pyridine.
Understand the role of pyridine: Pyridine acts as a base to neutralize the HCl byproduct formed during the reaction, facilitating the nucleophilic acyl substitution.
Recognize the mechanism: The reaction proceeds via nucleophilic acyl substitution where the hydroxyl group of cyclohexanol attacks the carbonyl carbon of the acyl chloride, leading to the formation of a tetrahedral intermediate.
Consider the leaving group: The chloride ion (Cl-) is a good leaving group, which will depart, allowing the reformation of the carbonyl group and the formation of an ester linkage.
Determine the major product: The major product of this reaction is an ester, specifically cyclohexyl ethanoate, formed by the replacement of the chloride in the acyl chloride with the cyclohexanol group.
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