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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4030

Menthyl chloride (2-isopropyl-5-methylcyclohexyl chloride in which Cl is trans to the isopropyl group; all three substituents are equatorial in its stable chair) and neomenthyl chloride (the diastereomer in which Cl is cis to the isopropyl group; in its stable chair Cl is axial while isopropyl and methyl are equatorial) are each treated with in ethanol (E2). Which statement is correct?

  1. Aneomenthyl chloride reacts much faster, but mainly gives 3-isopropyl-6-methylcyclohexene
  2. Bneomenthyl chloride reacts much faster, mainly giving 1-isopropyl-4-methylcyclohexene; menthyl chloride reacts slowly and gives only 3-isopropyl-6-methylcyclohexene
  3. Cboth react at about the same rate and give the same mixture of alkenes
  4. Dmenthyl chloride reacts faster because Cl is equatorial, mainly giving 1-isopropyl-4-methylcyclohexene

Answer: B

E2 needs Cl axial and an axial H on the adjacent carbon. Neomenthyl chloride already has Cl axial and both neighbouring carbons carry an axial H, so it reacts fast to give mainly the trisubstituted 1-isopropyl-4-methylcyclohexene (Saytzeff). Menthyl chloride must flip to the chair with Cl, isopropyl and methyl all axial; there the H on the isopropyl-bearing carbon is equatorial, so only the other neighbour gives an anti H, and slowly only the disubstituted 3-isopropyl-6-methylcyclohexene forms.
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