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Karnataka Board PUCPUC Science 2nd PUC Class 12

Give plausible explanation for the following: Cyclohexanone forms cyanohydrin in good yield but 2, 2, 6 trimethylcyclohexanone does not.

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Question

Give plausible explanation for the following:

Cyclohexanone forms cyanohydrin in good yield but 2, 2, 6 trimethylcyclohexanone does not.

Chemical Equations/Structures
Give Reasons
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Solution

Due to the presence of three methyl groups at α-places, nucleophilic attack of CN ions does not occur. This steric hindrance is absent in cyclohexane. Hence, nucleophilic attack of CN ions occurs quickly. Hence, cyclohexanone cyanohydrin is obtained in good yield.

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Chapter 8: Aldehydes, Ketones and Carboxylic Acids - Exercises [Page 257]

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NCERT Chemistry Part 1 and 2 [English] Class 12
Chapter 8 Aldehydes, Ketones and Carboxylic Acids
Exercises | Q 8.18 (i) | Page 257

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