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JEE Main 2022 · Chemistry · Carbonyl Compounds, Carboxylic Acids and Amines · easy

The number of compounds among the following that undergo the Cannizzaro reaction with concentrated NaOH is: HCHO, CH3CHO, C6H5CHO, (CH3)3C - CHO…

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The number of compounds among the following that undergo the Cannizzaro reaction with concentrated NaOH is: HCHO\mathrm{HCHO}, CH3CHO\mathrm{CH_3CHO}, C6H5CHO\mathrm{C_6H_5CHO}, (CH3)3C ⁣− ⁣CHO\mathrm{(CH_3)_3C\!-\!CHO}, CH3COCH3\mathrm{CH_3COCH_3}, furfural (furan-2-carbaldehyde), C6H5COCH3\mathrm{C_6H_5COCH_3}
  1. A. 3
  2. B. 5
  3. C. 4
  4. D. 6
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Answer: (C) 4

Cannizzaro disproportionation needs an aldehyde with no α\alpha-hydrogen. HCHO\mathrm{HCHO}, C6H5CHO\mathrm{C_6H_5CHO}, (CH3)3CCHO\mathrm{(CH_3)_3CCHO} and furfural all qualify (4). CH3CHO\mathrm{CH_3CHO} has α\alpha-H and undergoes aldol condensation instead; the two ketones, CH3COCH3\mathrm{CH_3COCH_3} and C6H5COCH3\mathrm{C_6H_5COCH_3}, are not aldehydes and also undergo aldol-type reactions. Answer: 4.
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