Which among the following groups is not reduced by BH3

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HPSC Assistant Professor 2018 Chemistry (Official Paper)
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  1. qImage66c0c6bc8a197dda8a16b0ce
  2. -NO2
  3. -COOH
  4. qImage66c0c6bd8a197dda8a16b104

Answer (Detailed Solution Below)

Option 2 : -NO2
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Detailed Solution

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Concept:

  • Reduction by Borane (BH3): Borane (BH3) is a selective reducing agent used in organic synthesis.

    • alkene: Borane reduces alkenes through hydroboration, adding across the double bond to form organoborane intermediates.

    • -NO2 (Nitro group): The nitro group is generally resistant to reduction by borane under normal conditions.

    • -COOH (Carboxylic acid): Carboxylic acids can be reduced by borane to form primary alcohols.

    • acetic anhydride: Borane can reduce anhydrides to alcohols or aldehydes.

Explanation:

  • qImage66c0c6bc8a197dda8a16b0ce

    • Borane reduces alkenes through hydroboration, forming organoboranes.

  • -NO2:

    • The nitro group is generally resistant to reduction by borane.

  • -COOH:

    • Borane reduces carboxylic acids to primary alcohols.

  • qImage66c0c6bd8a197dda8a16b104

    • Borane can reduce anhydride to alcohols or aldehydes.

Conclusion:

The group that is not reduced by BH3 is: -NO2

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