MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms IV: Elimination / Saytzeff vs Hofmann products
JEE Main levelSingle correct optionDifficulty 2 of 3o4062

2-Fluorobutane is heated with in ethanol. Unlike 2-bromobutane, the major alkene is

  1. Abut-1-ene
  2. Bethyl sec-butyl ether
  3. Cbut-2-ene (cis and trans together)
  4. Dbutan-2-ol

Answer: A

Fluoride is a poor leaving group and the strong C-F bond is broken late, so the E2 transition state has considerable carbanion character. The most acidic, least hindered primary hydrogen is removed, giving the Hofmann product but-1-ene. 2-Bromobutane, in contrast, gives mainly but-2-ene.
Practice Organic Reaction Mechanisms IV: Elimination More on Saytzeff vs Hofmann products

More questions on Saytzeff vs Hofmann products