Which two of the following compounds are reduced to the same chiral alditol by sodium borohydride?

II and III

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I and II

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III and IV

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II and IV

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Solution

The correct option is B I and II
To yield the same alditol, the configuration of the rest of the carbon chain (apart from the carbonyl carbon) should be the same. Species I and II yield the same alditol as shown in the scheme of reactions.

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L A H

S B H

The product obtained on oxidation of sodium borohydride by iodine is:

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