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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro229

The compound shown is first reduced with excess (then aqueous work-up) and the isolated product is oxidised with excess PCC in . Which structure is the final product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: D

The compound is dimethyl terephthalate. reduces both esters to give benzene-1,4-dimethanol. PCC stops at the aldehyde stage for primary alcohols, so both groups become and terephthalaldehyde results. The diacid would need Jones reagent, and the mono-aldehyde corresponds to incomplete oxidation with excess oxidant.
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