MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms IV: Elimination / E1 mechanism and carbocation rearrangement
JEE Main levelSingle correct optionDifficulty 2 of 3o4116

2,2-Dimethylpropan-1-ol (neopentyl alcohol) is heated with conc. . The major alkene formed is

  1. A2-methylbut-2-ene
  2. B2-methylbut-1-ene
  3. C3-methylbut-1-ene
  4. Dpent-1-ene

Answer: A

The alcohol has no beta-hydrogen, so direct elimination is impossible. Ionisation (with concerted methyl migration) gives the tertiary cation . Loss of H from the group gives the trisubstituted alkene 2-methylbut-2-ene.
Practice Organic Reaction Mechanisms IV: Elimination More on E1 mechanism and carbocation rearrangement

More questions on E1 mechanism and carbocation rearrangement