A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided. Concept introduction: By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O . Under these acidic conditions, no strong base should appear.

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Chapter 18, Problem 18.86P

Interpretation Introduction

Interpretation:

A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided.

Concept introduction:

By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O. Under these acidic conditions, no strong base should appear.

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