Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product obtained when the given alcohol is treated with concentrated H ₂ SO ₄ .
Options
- AAll the three will be formed in equal amounts
Correct answer
2
Step-by-step solution
The given alcohol is 1-phenyl-3-methylbutan-2-ol. Upon treatment with concentrated H ₂ SO ₄ , the hydroxyl group is protonated and leaves as a water molecule, forming a secondary carbocation: C ₆ H ₅- CH ₂- CH ( OH )- CH ( CH ₃)₂ H ⁺ C ₆ H ₅- CH ₂- CH ⁺- CH ( CH ₃)₂ + H ₂ O This secondary carbocation can undergo a 1,2-hydride shift to form a more stable carbocation. There are two possible shifts. A 1,2-hydride shift from the adjacent benzylic - CH ₂- group forms a secondary benzylic carbocation, which is highly sta