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JEE Main levelSingle correct optionDifficulty 2 of 3o4187

Potassium tert-butoxide gives a higher proportion of the Hofmann alkene than sodium ethoxide with the same alkyl halide mainly because:

  1. Ait is a weaker base than ethoxide, so the reaction becomes E1
  2. Bits bulk makes approach to the hindered internal beta-hydrogen difficult, so the more accessible terminal hydrogen is removed
  3. Cit changes the leaving group of the substrate
  4. Dthe less substituted alkene is always the more stable one

Answer: B

Both bases operate by E2. The tert-butoxide ion is very bulky, so steric hindrance disfavours attack on the internal (secondary or tertiary) C-H, and it removes the more exposed primary hydrogen instead. Its basicity is similar to or greater than that of ethoxide, and the less substituted alkene is the less stable one.
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