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JEE Main levelSingle correct optionDifficulty 2 of 3o4026

2-Bromo-2-methylbutane is treated with in . The major alkene is

  1. A2-methylbut-2-ene
  2. B3-methylbut-1-ene
  3. Cpent-2-ene
  4. D2-methylbut-1-ene

Answer: D

The very bulky tert-butoxide cannot easily reach the hindered internal CH2 hydrogens or the more crowded transition state leading to the trisubstituted alkene; it removes a hydrogen from a terminal CH3 instead. The major product is the less substituted 2-methylbut-1-ene (Hofmann), unlike with ethoxide, which gives mainly 2-methylbut-2-ene.
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