Quantrex Quantrex AcademyJEE · NEET · NDA PYQs with solutions Open app
Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

Which of the following substrates yields a rearranged product upon acid-catalyzed hydration?

Options

  1. ACH ₃- S - CH ₂- CH = CH ₂
  2. BCH ₃- CH = CH ₂

Correct answer

2

Step-by-step solution

Acid-catalyzed hydration of alkenes proceeds via the formation of a carbocation intermediate, which may undergo rearrangement (such as a hydride or alkyl shift) if a more stable carbocation can be formed. Let us analyze the intermediate formed for each substrate: For (A): Protonation of the double bond yields Ph₂C⁺-CH₂-C(CH₃)₃ . This is a tertiary carbocation that is highly resonance-stabilized by two phenyl groups. Since it is already exceptionally stable, it does not undergo any rearrangement. For (B): Protonatio

Practice Alcohols Phenols and Ethers on Quantrex Academy →

More from Alcohols Phenols and Ethers

All Alcohols Phenols and Ethers questions Full Alcohols Phenols and Ethers list All Fundamentals of Organic Chemistry PYQs