What sequence of reactions could be used to prepare

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

Question 1 options:

a) (1) Cl2, hv; (2) t-BuOK / t-BuOH; (3) Hg(OAc)2, H2O; (4) NaBH4, H3O+

b) (1) Cl2, hv; (2) t-BuOK / t-BuOH; (3) OsO4; (4) NaHSO3 / H2O

c) (1) Cl2, hv; (2) t-BuOK / t-BuOH; (3) H2O2

d) (1) t-BuOK / t-BuOH; (2) Cl2, hv; (3) NaOH / H2O

e) (1) NaOH / H2O; (2) Br2; (3) NaNH2 (2 eq.) / liq. NH3; (4) KMnO4, NaOH / H2O, 5o C

1 Answer

  • option a will make cyclopentanol.

    If alkene is reacted with peroxide, it will give epoxide (not sure about option c though)

    the first three steps in e is used t make an alkyne (which I’m not sure the reaction is going to happen with cyclopentane)

    b will do. OsO4 can also be replaced by KMnO4

    Source(s): wade – organic chemistry chapter 7,8

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