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Question

Give a plausible explanation for the following.
Cyclohexanone forms cyanohydrins in good yield but 2,2,6 - trimethyl cyclohexanone does not.

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Solution

Cyclohexanones form cyanohydrins according to the following equation shown on the figure i.
Here the nucleophile CNcan easily attack without any steric hindrance.
However, in the case of 2,2,6 trimethylcyclohexanone. CH3 groups at α positions offersteric hindrances and as a result . CNcan not attack effectively. See the figure ii.
2,2,6- trimethylcyclohexanone.

1057847_1117717_ans_2ffc1887a9a446ac8819a9a14c1ccd1c.png

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