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Equations for the sodium borohydride reduction of benzil to hydro benzoin
Accepted Answer
The reduction of benzil to hydrobenzoin using sodium borohydride (NaBH4) is a classic example of a nucleophilic addition reaction. Here's the simplified equation:
Ph-C(=O)-C(=O)-Ph + 2 NaBH4 + 2 H2O → Ph-CH(OH)-CH(OH)-Ph + 2 NaBO2 + 4 H2
Key points:
Benzil: A diketone with two carbonyl groups (C=O) attached to phenyl rings.
NaBH4: A reducing agent, providing the hydride ions (H-) needed for the reaction.
Hydrobenzoin: The product, a diol with two hydroxyl groups (OH) attached to adjacent carbons.
NaBO2: Sodium borate, a by-product.
H2: Hydrogen gas, also a by-product.
Mechanism:
1. Hydride ions from NaBH4 attack the carbonyl groups of benzil, reducing them to alcohol groups.
2. The reaction proceeds stepwise, with one carbonyl group being reduced at a time.
3. The final product is hydrobenzoin, a chiral compound with two stereocenters.
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