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JEE Main levelSingle correct optionDifficulty 2 of 3co078

Each pair of carbonyl compounds below is mixed with dilute NaOH at low temperature. Counting only aldol addition products (no dehydration, ignoring stereoisomers), which pair can give the largest number of different products?

  1. Aethanal and benzaldehyde
  2. Bpropanone and benzaldehyde
  3. Cmethanal and 2,2-dimethylpropanal
  4. Dethanal and propanal

Answer: D

Ethanal and propanal both have alpha-hydrogens, so each can be nucleophile or electrophile: 2 self products and 2 crossed products, a total of 4. Ethanal with benzaldehyde and propanone with benzaldehyde each give 2 (self plus crossed). Methanal with 2,2-dimethylpropanal has no alpha-hydrogens and gives no aldol product.
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