Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
When the following alcohol is treated with concentrated H ₂ SO ₄ , what is the major product obtained?
Options
- AAll three products are formed in equal amounts.
Correct answer
2
Step-by-step solution
The given reactant is 1-phenyl-3-methylbutan-2-ol, which has the structure C ₆ H ₅- CH ₂- CH(OH) - CH(CH ₃)₂ . When treated with concentrated H ₂ SO ₄ , the hydroxyl group is protonated and leaves as a water molecule, generating a secondary carbocation at C-2: C ₆ H ₅- CH ₂- C ^+ H - CH(CH ₃)₂ This intermediate carbocation can undergo a 1,2-hydride shift from the adjacent C-1 (benzylic position) to form a highly resonance-stabilized secondary benzylic carbocation: C ₆ H ₅- C ^+ H - CH ₂- CH(CH ₃)₂ Elimination of a