One or more options correct
Benzaldehyde and an excess of formaldehyde are treated with concentrated aqueous NaOH (crossed Cannizzaro reaction). The correct statement(s) is(are)
- A. is obtained as the reduction product
- B. Sodium formate is obtained as the oxidation product
- C. Sodium benzoate is the major carboxylate formed because the aromatic aldehyde is the better hydride donor
- D. If is used instead of , the alcohol obtained is
Show answer and solution
Answer: A, B, D
Neither aldehyde has an -hydrogen, so hydroxide adds to a carbonyl to give a hydrate anion that transfers hydride to a second aldehyde molecule. Formaldehyde is far more electrophilic and is hydrated much more easily, so its hydrate anion is the hydride donor and it is oxidised to formate, while benzaldehyde, the hydride acceptor, is reduced to benzyl alcohol; (A) and (B) are correct and (C) is wrong because the donor is formaldehyde, not benzaldehyde. With the transferred species is a deuteride, which ends on the carbonyl carbon of benzaldehyde: , giving (racemic, with the formate being ); (D) is correct.
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