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Cyclohexanone forms a cyanohydrin in good yield but 2,2,6-trimethylcyclohexanonedoes not. Explain.

Short Answer

Expert verified

2,2,6-trimethylcyclohexanone does not form cyanohydrin in good yield due to the presence of steric hindrance in it.

Step by step solution

01

Step 1:Nucleophile addition of HCN

Nucleophilic addition reaction on 鈥淎ldehydes and unhindered ketones鈥 with HCN results in the formation of cyanohydrins with the chemical formula (RCH(OH)C N).

Nucleophile addition of hydrogen cyanide (HCN) on carbonyl carbon is a 鈥渞eversible and base-catalyzed鈥漜hemical reaction.

02

Step 2: Hindered Ketone 

The nucleophile addition of cyanide to the carbonyl group of ketone 2,2,6trimethylcyclohexanone is the reversible reaction; cyanohydrin formation is an equilibrium process.

2,2,6 trimethylcyclohexanone is sterically hindered by the presence of three methyl groups, making it difficult to attack the upcoming nucleophile cyanide (CN-)on the carbonyl carbon; therefore, the equilibrium of the reaction lies toward the side of unreacted ketone more than the product cyanohydrin.

The equilibrium favoured toward the unreacted ketone is shown as follows:

Formation of cyanohydrin not favoured

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