Acid-Catalyzed Dehydration of Alcohols and Hydration of Alkenes
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.
Strategy
The key to part (a) is that when acid-catalyzed dehydration of an alcohol can yield isomeric alkenes, the alkene with the greater number of alkyl groups on the carbon atoms of the double bond generally predominates. After the structural formula of A is determined, use Markovnikov’s Rule to predict the structural formula of compound B.
