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JEE Main levelSingle correct optionDifficulty 2 of 3o4186

2-Fluorobutane is heated with in ethanol. Unlike 2-bromobutane, the major alkene is but-1-ene. This is best explained by:

  1. Afluoride is a poor leaving group, so the transition state has carbanion character and favours removal of the more acidic, less hindered primary hydrogen
  2. Bfluoride is an excellent leaving group, giving a very early transition state with no regioselectivity
  3. Cfluorine is highly electronegative so the reaction goes by E1 with a stable carbocation
  4. Dthe more substituted alkene but-2-ene is much less stable than but-1-ene

Answer: A

Because the C-F bond is strong and leaves poorly, C-H breaks ahead of C-F in the transition state (E1cB-like). Carbanion character favours the less substituted, less alkyl-destabilised, more accessible site, giving the Hofmann product but-1-ene.
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