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Question

Which reagents would convert cyclohexene to trans-1,2-cyclohexenediol?

A
OsO4,(CH3)3CCOOH,(CH3)3COH,NaOH
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B
O3 followed by Zn/H2O
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C
CH3CO3H followed by NaOH/H2O
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D
HIO4
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Solution

The correct option is D CH3CO3H followed by NaOH/H2O
OsO4 with alkene forms osmate ester which can be hydrolyzed to produce a cis-glycol and regenerate the osmium tetroxide.

Ozonolysis O3+Zn/H2O splits the alkene at double bond and forms two aldehydes.

Peracid CH3CO3H forms epoxide with alkene. Epoxide on reaction with NaOH/H2O produces trans vicinal diol.

With HIO4 alkene undergoes oxidative cleavage to form to aldehydes.

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