Treatment of an aldehyde or ketone with cyanide ion (-: C ≡N), followed by protonation of the te

step 1 This question asks us what happens whenever we treat cyclohexanone. So cyclohexane with a CO dou

Treatment of an aldehyde or ketone with cyanide ion (-: C...

Treatment of an aldehyde or ketone with cyanide ion $(-: \mathrm{C} \equiv \mathrm{N})$, followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin. Show the structure of the cyanohydrin obtained from cyclohexanone.

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Key Concepts

Nucleophilic Addition Reaction

This concept refers to the process where a nucleophile, rich in electrons, adds to the electrophilic carbon of a carbonyl group. In the context of this reaction, the cyanide ion attacks the electrophilic carbonyl carbon of the ketone, leading to the formation of a new carbon–carbon bond and a tetrahedral intermediate.

Cyanide Ion as a Nucleophile

The cyanide ion is an effective nucleophile due to its high electron density and the presence of a lone pair. Its linear structure and the negative charge on the carbon allow it to attack electrophilic carbon centers, such as those in aldehydes and ketones.

Cyanohydrin Formation

Cyanohydrin formation involves the addition of a cyanide ion to a carbonyl compound (aldehyde or ketone) to form a cyanohydrin. After the initial attack and formation of a tetrahedral alkoxide ion intermediate, a protonation step converts the alkoxide into the corresponding hydroxyl group, resulting in a cyanohydrin.

Reaction Mechanism and Tetrahedral Intermediate

The reaction mechanism involves a two-step process: first, the nucleophilic attack of the cyanide ion on the carbonyl group forms a tetrahedral alkoxide intermediate; second, protonation of this intermediate yields the cyanohydrin. Understanding this mechanism is crucial for predicting product structure and stereochemistry.

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