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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4208

Ethyl(isopropyl)dimethylammonium hydroxide, , is heated. The major products are:

  1. Apropene and N-ethyl-N,N-dimethylamine
  2. Bpropene and trimethylamine
  3. Cethene and N,N-dimethylpropan-2-amine
  4. Dethene and trimethylamine

Answer: C

In Hofmann elimination the beta-hydrogen most easily removed is on the least substituted carbon; ethyl beta-hydrogens (methyl, three H) are preferred over the six isopropyl methyl hydrogens. The ethyl group leaves as ethene and the tertiary amine isopropyl-dimethylamine (, N,N-dimethylpropan-2-amine) is the other product.
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