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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3041

Substrates in List I are heated in ethanol (no added base). Match each with the principal substitution product in List II. List I: (P) 1-bromo-1-methylcyclohexane; (Q) bromobenzene; (R) neopentyl bromide, ; (S) 2-bromo-3,3-dimethylbutane. List II: (1) 2-ethoxy-2,3-dimethylbutane; (2) 2-ethoxy-2-methylbutane; (3) 1-ethoxy-1-methylcyclohexane; (4) no substitution product (essentially unreactive).

  1. AP-3, Q-4, R-2, S-1
  2. BP-3, Q-4, R-1, S-2
  3. CP-3, Q-2, R-4, S-1
  4. DP-1, Q-4, R-2, S-3

Answer: A

P gives the tertiary cation without rearrangement, so ether 3. Q cannot ionise (aryl cation), so 4. R undergoes methyl migration during ionisation to , giving 2. S undergoes a methyl shift to , giving 1.
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