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When compared to sodium borohydride, sodium cyanoborohydride is a(n) Choose your answer here selective hydride-reducing reagent.

Question

When compared to sodium borohydride, sodium cyanoborohydride is a(n) ___ selective hydride-reducing reagent.

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Solution

When compared to sodium borohydride, sodium cyanoborohydride is a more selective hydride-reducing reagent.

Here's why:

  1. Sodium borohydride (NaBH4) is a strong reducing agent that rapidly reduces aldehydes and ketones to alcohols. It is less selective and can reduce a wide range of functional groups.

  2. Sodium cyanoborohydride (NaBH3CN), on the other hand, is a mild reducing agent. It is more selective because it only reduces imines and reductive aminations.

  3. The presence of the cyanide group in sodium cyanoborohydride slows down the rate of hydride transfer, making it more selective.

  4. This selectivity is useful in organic synthesis where you want to reduce one functional group without affecting others.

So, sodium cyanoborohydride is a more selective hydride-reducing reagent compared to sodium borohydride.

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