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Example · Example 25

Q.Acetone is treated with NaBH4\text{NaBH}_4 in methanol. Identify the product and state whether LiAlH4\text{LiAlH}_4 would give a different outcome for this particular substrate.

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NaBH4\text{NaBH}_4 delivers a hydride ion to the electrophilic carbonyl carbon of acetone, giving a tetrahedral alkoxide that is protonated (by the methanol solvent) to give the secondary alcohol, propan-2-ol. LiAlH4\text{LiAlH}_4 is a considerably more powerful and reactive hydride donor overall, and must be handled under strictly anhydrous, aprotic conditions -- but for a simple substrate like acetone, which contains only the one carbonyl group and no other easily-reduced functionality (such as an isolated C=C\text{C=C} double bond, an ester, or a nitrile) for the reagents' differing reactivity/selectivity to distinguish between, both reagents simply reduce the carbonyl to the alcohol and give …

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