Question

acid-catalyzed hydration of 1-methylcyclohexene gives two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explain

Answer 1

Answer:

Major product does not undergo oxidation since it is a tertiary alcohol whereas minor product undergoes oxidation to ketone as it is  secondary alcohol.

Explanation:

Hello,

In this case, given the attached picture, the hydration of the 1 methylcyclohexene yields to alcohols; 1-methylcyclohexan-1-ol and 1-methylcyclohexan-2-ol. Thus, since the OH in the 1-methylcyclohexan-1-ol (major product) is bonded to a tertiary carbon (bonded with other three carbon atoms) it is not able to increase the number of oxygen bonds (oxidation) as it already attained the octet whereas the 1-methylcyclohexan-2-ol (minor product) is able to undergo oxidation to ketone as the carbon bonded to it is secondary (bonded with other two carbon atoms), so one extra bond the oxygen is allowed to be formed to carbonyl.

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