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 CN−can 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 . CN−can not attack effectively. See the figure ii.