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Question 64

Given below are two statements:

Statement I: 2,6-diethylcyclohexanone and 6-methyl-2-n-propylcyclohexanone are metamers.

Statement II: 2,2,6,6-tetramethylcyclohexanone exhibits keto-enol tautomerism.

In the light of the above statements, choose the correct answer from the options given below:

Metamerism arises due to the different distribution of alkyl groups on either side of the same polyvalent functional group while retaining the same molecular formula.

In 2,6-diethylcyclohexanone, the carbonyl group is associated with two ethyl substituents, whereas in 6-methyl-2-(n)-propylcyclohexanone, it is associated with a methyl group and an (n)-propyl group. Both compounds have the same molecular formula but differ in the distribution of alkyl groups around the carbonyl functionality. Hence, they are metamers.

Therefore, Statement I is true.

Keto-enol tautomerism requires the presence of at least one (\alpha)-hydrogen atom adjacent to the carbonyl group.

In 2,2,6,6-tetramethylcyclohexanone, both (\alpha)-carbon atoms are fully substituted by two methyl groups each and do not possess any (\alpha)-hydrogen atoms. Consequently, the compound cannot undergo keto-enol tautomerism.

Therefore, Statement II is false.

Hence, Statement I is true, Statement II is false, and the correct answer is Option C.

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