Cyclohexene on reaction with `m-`chloroperoxbenzpic acid forms a compound `(X)` which on treatement with dilute `H_(2)SO_(4)` produces a compound `(Y)`. The compound `(Y)` is

Options

A. `(+)-`cis`-1,2`-cyclohexanediol
B. `(+-)`trans`-1,2-`cyclohexanediol
C. cyclohexanol
D. cyclohexanone

Answer

B

Explanation

It is anti hydroxylation

where `RCOO_(2)H` stands for `m-`chloroperoxbenzonic acid. The initial product of the reaction of a peroxyacid such as `m`-chloroperoxobenzoic acid is a `3-`membered ring ether called an epoxide or oxirane (Prileschaiev's reaction):

The epoxide has the same geometry as teh alkene reactant:

The epoxide can be considered as the oxygen analog of a halonium ion without a positive charge. however, it is isolable unlike the halonium ion. The `HO` of the peroxyacid can be considered as an `E^(+)`. However, the : `Nu^(-)` portion, `RCOO^(-)` removes the hydrogen from `OH` as the `O` bonds to the `C=C`, giving the epoxide directly. The `RCOOH` in the reaction mixture has sufficient acidity to catalyze the opening of the epoxide ring by `H_(2)O` in the same anto fashion as does the halonium ion ring:

Thus cis-but`-2-`ene yields rac`-CH_(3)CHOHCHOHCH_(3)` while trans-but`-2-`ene yields mseo -`CH_(3)CHOHCHOHCH_(3)`