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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4209

Which reactions give the less substituted (Hofmann) alkene as the major product?

  1. A2-Fluorohexane with in ethanol
  2. B2-Iodohexane with in ethanol
  3. C2-Chloro-2-methylbutane with in
  4. DHexan-2-ol with conc. at high temperature

Answer: A, C

Fluoride is a poor leaving group and gives Hofmann orientation. The bulky tert-butoxide gives the less hindered alkene 2-methylbut-1-ene. 2-Iodohexane with small ethoxide follows Saytzeff to give hex-2-ene, and acid dehydration (E1) gives the more stable hex-2-ene major. Statements 1 and 3 are correct.
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