JEE Main Chemistry question

Which of the following will give *trans*-diols?

(A)Alkene + (1) KMnO (2) HO — cold, dilute (gives *cis*-diol)
(B)Alkene + (1) OsO (2) NaSO (gives *cis*-diol)
(C)Cyclic alkene + (1) OsO, 25 °C (2) NaSO (gives *cis*-diol)
(D)Cyclic alkene + 35% HO, HCOH, 25 °CCorrect

Answer: (D)

Solution

Cold dilute KMnO and OsO both perform *syn*-dihydroxylation (both new OH groups added to the same face), giving the *cis*-diol. Peroxyformic acid (HO/HCOOH) instead first forms an

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Question ID VK-142375