Asked in Premeth Test 43 — Alcohols and Phenols

Among the following alkenes, which one produces a tertiary butyl alcohol on acid-catalyzed hydration?

Correct answer: C. 2-Methylpropene

  • A. 2-Butene
  • B. 1-Butene
  • C. 2-Methylpropene
  • D. 1-Pentene

Explanation

Acid-catalyzed hydration of an alkene follows Markovnikov's rule, proceeding through the most stable carbocation intermediate. The hydration of 2-methylpropene forms a stable tertiary carbocation, which then adds water to yield tertiary butyl alcohol.

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About Alcohols and Phenols

Alcohols are classified as primary, secondary or tertiary and studied through their hydrogen bonding, acidity, oxidation and reactions with active metals, acids and halogenating agents. Phenols require separate treatment because the hydroxyl group is attached to an aromatic ring, making their acidity and electrophilic substitution different from ordinary alcohols.

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