Single correct option
The major product when 3-methylbutan-2-ol is treated with concentrated HBr is
- A. 1-bromo-2-methylbutane
- B. 1-bromo-3-methylbutane
- C. 2-bromo-3-methylbutane
- D. 2-bromo-2-methylbutane
Show answer and solution
Answer: (D) 2-bromo-2-methylbutane
The secondary alcohol is protonated and loses water giving the secondary carbocation . A 1,2-hydride shift moves the cation to the adjacent tertiary carbon, , which is more stable. Attack by gives 2-bromo-2-methylbutane as the major product, and 2-bromo-3-methylbutane (direct substitution) is minor.
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