What sequence of reactions could be used to prepare cis-1,2-cyclopentanediol from cyclopentane?
A) (1) Cl2,h ; (2) t-BuOK/t-BuOH; (3) OsO4; (4) NaHSO3/H2O
B) (1) t-BuOK/t-BuOH; (2) Cl2,h ; (3) NaOH/H2O
C) (1) Cl2,h ; (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 ; (2) t-BuOK/t-BuOH; (3) Hg(OAc) 2,H2O (4) NaBH4,H3O+
Correct Answer:
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