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JEE Advanced 2020 Paper 2 · Chemistry · Carbonyl Compounds, Carboxylic Acids and Amines · medium

Reactions is/are correctly described?

One or more options correct

Which of the following reactions is/are correctly described?
  1. A. Benzaldehyde heated with excess formaldehyde in concentrated NaOH\mathrm{NaOH} gives benzyl alcohol and sodium formate (crossed Cannizzaro reaction).
  2. B. Acetophenone with I2/NaOH\mathrm{I_2/NaOH} gives iodoform and sodium benzoate.
  3. C. Pentan-3-one on warming with I2/NaOH\mathrm{I_2/NaOH} gives a yellow precipitate of iodoform.
  4. D. Benzaldehyde in dilute NaOH\mathrm{NaOH} undergoes self aldol condensation to give cinnamaldehyde.
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Answer: A, B

Option A: benzaldehyde has no α\alpha-hydrogen and neither does formaldehyde; in the crossed Cannizzaro reaction the more reactive, unhindered formaldehyde adds hydroxide and donates hydride, so it is oxidised to formate, while benzaldehyde accepts the hydride and is reduced to PhCH2OH\mathrm{PhCH_2OH}, so A is correct. Option B: PhCOCH3\mathrm{PhCOCH_3} is a methyl ketone, so haloform cleavage gives CHI3\mathrm{CHI_3} and PhCOO−Na+\mathrm{PhCOO^-Na^+}, and B is correct. Option C: pentan-3-one, CH3CH2COCH2CH3\mathrm{CH_3CH_2COCH_2CH_3}, has no CH3CO\mathrm{CH_3CO} group (the carbonyl is flanked by ethyl groups), so it gives no iodoform; C is wrong. Option D: benzaldehyde lacks α\alpha-hydrogens and cannot form an enolate, so it cannot undergo self aldol condensation. Cinnamaldehyde would need acetaldehyde as the enolisable partner in a crossed aldol reaction, so D is wrong.
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