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  • Give plausible explanation for each of the following : (i) Cyclohexanone forms cyanohydrin in good yield but 2, 2, 6- trimethylcyclohexanone does not

Q 12.18     Give plausible explanation for each of the following:

          (i)     Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not. 

Answers (1)

best_answer

Structure of 2,2,6-trimethylcyclo hexanone

Cyclohexanone forms cyanohydrin when the nucleophile (HCN/CN^{-}) attack on cyclohexanone.

In this case, there is less hindrance around the CO group so the nucleophile can attack easily. But in case of 2,2,6-trimethylcyclo hexanone at the alpha (\alpha) position, there is a hindrance because of the methyl groups. Thus the nucleophile cannot attack effectively.

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manish

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