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Consider the reaction sequence: alkene + MCPBA -> A; A + H3O+ -> B; B + HIO4 -> C + D. Which of the following statements is correct?

1. B is a geminal diol
2. A is a vicinal diol
3. C and D can be distinguished by treatment with NaOH/I2
4. C and D can be distinguished by Tollen's reagent

Correct answer: C and D can be distinguished by Tollen's reagent

Solution

MCPBA converts the alkene to an epoxide (A). Acid-catalyzed hydrolysis opens the epoxide to give a trans-vicinal diol (B, not geminal). HIO4 cleaves the vicinal diol to give two carbonyl compounds (C and D). Since C and D are an aldehyde and a ketone, Tollen's reagent (which oxidizes only aldehydes) can distinguish between them.

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