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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4069

Select all combinations in which the substrate, reagent and major product are correctly matched.

  1. A with alcoholic gives but-2-ene
  2. Bpentan-2-yl trimethylammonium hydroxide on heating gives pent-1-ene
  3. C3-bromo-3-methylpentane with /ethanol gives 3-methylpent-1-ene
  4. D1-bromo-1-methylcyclohexane with /ethanol gives 1-methylcyclohexene

Answer: A, B, D

2-Bromobutane gives the Saytzeff alkene but-2-ene, and the quaternary ammonium hydroxide gives the Hofmann alkene pent-1-ene. 1-Bromo-1-methylcyclohexane with ethoxide gives the trisubstituted endocyclic alkene 1-methylcyclohexene. The third pair is impossible: in 3-bromo-3-methylpentane, C-3 is attached to C-2, C-4 and the methyl group, so the double bond can only be 3-methylpent-2-ene or 2-ethylbut-1-ene, and 3-methylpent-1-ene cannot form.
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