Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Which of the following substrates yields a rearranged product upon acid-catalyzed hydration?
Options
- ACH ₃- S - CH ₂- CH = CH 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