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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3co251

Which statements are correct for the compound shown?

  1. A followed by acidification gives the hydroxymethyl benzoic acid (only the CHO is reduced)
  2. BExcess followed by aqueous work-up reduces both groups to give a benzenedimethanol
  3. CHydrazine and KOH at high temperature (Wolff-Kishner), then acidification, give a methylbenzoic acid
  4. D also reduces the carboxylic acid group to CH2OH

Answer: A, B, C

The drawn compound is 3-formylbenzoic acid. NaBH4 reduces aldehydes but not carboxylic acids (carboxylate). LiAlH4 reduces both CHO and COOH to CH2OH, giving 1,3-benzenedimethanol. Wolff-Kishner reduces CHO to CH3 and leaves the carboxylate, giving 3-methylbenzoic acid after acidification. Statement 4 is wrong.
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