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JEE Advanced levelSingle correct optionDifficulty 3 of 3st082

Column I lists compounds and Column II lists the number of meso stereoisomers each has. Column I: (P) butane-2,3-diol; (Q) pentane-2,3,4-triol; (R) heptane-2,3,4,5,6-pentol, ; (S) pentane-2,3-diol. Column II: (1) 0; (2) 1; (3) 2; (4) 4.

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

Answer: A

For a symmetric chain with n identical centres, count the left/right vectors that are palindromic and group them by rotation. This gives 1 meso form for n=2, 2 for n=3 and 4 for n=5 (computed by enumeration). Pentane-2,3-diol is unsymmetrical and has none. Thus P-1 meso, Q-2, R-4, S-0, which is P-2, Q-3, R-4, S-1 in Column II labels.
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