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Question 14.4: In part (a), acid-catalyzed dehydration of 2-methyl-3-pentan...

In part (a), acid-catalyzed dehydration of 2-methyl-3-pentanol gives predominantly Compound A. Treatment of Compound A with water in the presence of sulfuric acid in part (b) gives Compound B. Propose structural formulas for Compounds A and B.

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Solution
(a) Acid-catalyzed dehydration of 2-methyl-3-pentanol gives predominantly
2-methyl-2-pentene, an alkene with three substituents on its double bond: two methyl groups and one ethyl group.

(b) Acid-catalyzed addition of water to this alkene gives 2-methyl- 2-pentanol in accord with Markovnikov’s rule (Section 12.6B).

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