Video: Preparation of Diols and Pinacol Rearrangement
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SOLVED:1,2-Diols are converted to carbonyl compounds when treated with strong acids, in a reaction called the pinacol rearrangement. Draw a stepwise mechanism for this reaction.
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SOLVED:As we saw in Section 8-8,1,2 -diols undergo a cleavage reaction to give carbonyl-containing products on treatment with periodic acid, HIO4. The reaction occurs through a five-membered cyclic periodate intermediate: When diols A and B were prepared and the rates of their reaction with HIO4 were measured, it was found that diol A cleaved approximately 1 million times faster than diol B. Make molecular models of 𝐀 and 𝐁 and of the potential periodate intermediates, and explain the results.
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