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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

  1. 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

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