Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

What is the IUPAC name of the product of hydration of propene in the presence of dilute sulphuric acid?

Options:

2-Methylpropan-2-ol

Propan-1-ol

Propan-2-ol

2-Methylbutan-2-ol

Correct Answer:

Propan-2-ol

Explanation:

The correct answer is Option (3) → Propan-2-ol

Hydration of propene (CH₃–CH=CH₂) in the presence of dilute H₂SO₄ follows Markovnikov's rule:

  • The alkene is protonated to form the more stable carbocation: CH₃–CH⁺–CH₃ (secondary carbocation), not CH₃–CH₂–CH₂⁺ (primary).
  • Water then adds to this carbocation, and after deprotonation, the product is CH₃–CH(OH)–CH₃ (propan-2-ol).

This is acid-catalyzed electrophilic addition (oxymercuration-demercuration gives the same product, but here it's specified as dilute H₂SO₄).

IUPAC Name:

The longest chain is 3 carbons, with the –OH group on carbon 2 (lowest locant). Thus, propan-2-ol.

Why others are incorrect:

  • 2-Methylpropan-2-ol: Product from hydration of 2-methylpropene (isobutene), a tertiary alcohol.
  • Propan-1-ol: Would form only if anti-Markovnikov addition occurred (e.g., via hydroboration), but not with dilute H₂SO₄.
  • 2-Methylbutan-2-ol: Product from hydration of 2-methylbut-1-ene or 2-methylbut-2-ene.