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JEE Main levelSingle correct optionDifficulty 2 of 3co084

Ethanal and 2,2-dimethylpropanal are mixed in the presence of dilute NaOH at low temperature (no dehydration). The main crossed aldol addition product is

  1. A3-hydroxy-2,2-dimethylbutanal
  2. B3-hydroxy-2,4,4-trimethylpentanal
  3. C3-hydroxy-4,4-dimethylpentanal
  4. D4,4-dimethylpent-2-enal

Answer: C

Only ethanal has alpha-hydrogens, so its enolate is the nucleophile. 2,2-Dimethylpropanal is the electrophile. The product is , 3-hydroxy-4,4-dimethylpentanal. Dehydration would give the enal, which is not formed in the cold.
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