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Which of these aldehydes will UNDERGO the Cannizzaro reaction (disproportionation under concentrated NaOH)?
AAcetaldehyde, $\mathrm{CH_3CHO}$
BPropanal, $\mathrm{CH_3CH_2CHO}$
CButyraldehyde, $\mathrm{CH_3CH_2CH_2CHO}$
D$\mathrm{HCHO}$ and $\mathrm{C_6H_5CHO}$ — no $\alpha$-H
Answer & Solution
Correct answer: D. $\mathrm{HCHO}$ and $\mathrm{C_6H_5CHO}$ — no $\alpha$-H
1. The CANNIZZARO reaction is a base-induced DISPROPORTIONATION: one molecule of the aldehyde is OXIDISED to the carboxylic acid (or carboxylate) while another is REDUCED to the alcohol.
2. Crucial requirement: the aldehyde MUST NOT have an $\alpha$-HYDROGEN. (With $\alpha$-H, the molecule undergoes ALDOL condensation instead — a faster, competing reaction.)
3. Formaldehyde ($\mathrm{HCHO}$) has NO $\alpha$-carbon at all, so no $\alpha$-H → Cannizzaro applies. Two HCHO + NaOH → HCOOH(salt) + $\mathrm{CH_3OH}$.
4. Benzaldehyde ($\mathrm{C_6H_5CHO}$): the $\alpha$ position is a benzene-ring carbon with no extractable H → Cannizzaro applies. $2\,\mathrm{C_6H_5CHO} \xrightarrow{\text{NaOH}} \mathrm{C_6H_5COO^-} + \mathrm{C_6H_5CH_2OH}$.
5. Acetaldehyde, propanal, butyraldehyde ALL have $\alpha$-H — they undergo aldol, not Cannizzaro. So options A, B, C are wrong.
_Source: NCERT Class 12 Chemistry Part 2, Ch 8, §8.4 (Chemical Reactions — Cannizzaro reaction), p. 13–14._
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