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NEETChemistryAlcohols Phenols and Ethers

Consider the following reactions of 3-methylpentan-2-ol: Reaction 1: Treatment with HBr yields major product A. Reaction 2: Treatment with SOCl₂ yields major product B. Identify the IUPAC names of products A and B.

Options

  1. AA = 3-bromo-3-methylpentane, B = 3-chloro-3-methylpentane
  2. BA = 2-bromo-3-methylpentane, B = 2-chloro-3-methylpentane
  3. CA = 3-bromo-3-methylpentane, B = 2-chloro-3-methylpentane
  4. DA = 2-bromo-3-methylpentane, B = 3-chloro-3-methylpentane

Correct answer

C. A = 3-bromo-3-methylpentane, B = 2-chloro-3-methylpentane

Step-by-step solution

Reaction 1 (with HBr ): The reaction proceeds via a carbocation intermediate. Protonation and loss of water from 3-methylpentan-2-ol forms a secondary carbocation at C-2. A 1,2-hydride shift occurs from C-3 to C-2 to form a more stable tertiary carbocation. Nucleophilic attack by Br^- yields 3-bromo-3-methylpentane as the major product (A). Reaction 2 (with SOCl₂ ): The reaction of alcohols with thionyl chloride ( SOCl₂ ) follows an S_Ni (or S_N2 in the presence of a base) mechanism. This mechanism does not involve

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