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How is the cyano (CN) group of a cyanohydrin hydrolyzed to a carboxy (COOH) group?

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Final answer:

The cyano (CN) group of a cyanohydrin is hydrolyzed to a carboxy (COOH) group through the addition of water molecules. This reaction is typically catalyzed by an acid or a base.

Step-by-step explanation:

The cyano (CN) group of a cyanohydrin is hydrolyzed to a carboxy (COOH) group through a process called hydrolysis. In hydrolysis, the cyano group (-CN) is replaced by a hydroxyl group (-OH) through the addition of water molecules. This reaction is typically catalyzed by an acid or a base.

Here is the mechanism for the hydrolysis of a cyanohydrin:

  • The water molecule acts as a nucleophile, attacking the carbon atom of the cyano group.
  • This leads to the formation of a new bond between the carbon and the oxygen of the water molecule.
  • Simultaneously, the oxygen of the cyano group loses its bond to the nitrogen, forming a hydroxyl group.
  • The nitrogen atom gains a positive charge and is subsequently protonated by an acid or deprotonated by a base to form the carboxylic acid (-COOH) group.

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