What Sequence of Reactions Could Be Used to Prepare Cis-1,2-Cyclopentanediol $\nu$

question 41

Multiple Choice

What sequence of reactions could be used to prepare cis-1,2-cyclopentanediol from cyclopentane?

• A) (1)Cl₂,h\(\nu\); (2)t-BuOK/t-BuOH; (3)OsO₄; (4)NaHSO₃/H₂O
• B) (1)t-BuOK/t-BuOH; (2)Cl₂,h\(\nu\); (3)NaOH/H₂O
• C) (1)Cl₂,h\(\nu\); (2)t-BuOK/t-BuOH; (3)H₂O₂
• D) (1)NaOH/H₂O; (2)Br₂; (3)NaNH₂(2eq. )/liq.NH₃; (4)KMnO₄,NaOH/H₂O,5°C
• E) (1)Cl₂,h\(\nu\); (2)t-BuOK/t-BuOH; (3)Hg(OAc)₂,H₂O (4)NaBH₄,H₃O⁺

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