When cyclohexanone is heated in the presence of large amount of acetone cyanohydrin and small...

Question:

When cyclohexanone is heated in the presence of large amount of acetone cyanohydrin and small amount of base ,cyclohexanone and acetone is formed propose a mechanism.

Cyanohydrin:

A functional group that consists of a carbon atom to which a cyano group (-CN) and a hydroxyl group (-OH) are attached is called a cyanohydrin. It general formula is {eq}{{\rm{R}}_{\rm{2}}}{\rm{C}}\left( {{\rm{OH}}} \right){\rm{CN}} {/eq}, where R represents the hydrogen atom, an alkyl group or an aryl group.

Answer and Explanation:


The reaction occurs between cyclohexanone and acetocyanohydrin in the presence of a base to form cyclohexanone cyanohydrin and acetone. The general reaction is shown below.

The first step of the mechanism involves the deprotonation of the acetocyanohydrin by a base. In the second step, the shift of electrons occurs from the oxyanion followed by the attack of nucleophile which is cyanide ion on cyclohexanone. In the final step, the protonation of the anion results in the formation of a final product. The complete mechanism is shown below.


Learn more about this topic:

Aldehydes & Ketones: Reaction Mechanisms
Aldehydes & Ketones: Reaction Mechanisms

from AQA A-Level Chemistry: Practice and Study Guide

Chapter 15 / Lesson 1
10K

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