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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1209

Phthalic anhydride is treated with: (i) (1 equiv), room temperature; (ii) ; (iii) (2 equiv), 0\,^\circ\mathrm{C}. The final product is

  1. Amethyl 2-(methylcarbamoyl)benzoate
  2. Bdimethyl phthalate
  3. CN1,N2-dimethylbenzene-1,2-dicarboxamide
  4. DN-methylphthalimide

Answer: A

(i) ring-opening by methanol gives 2-(methoxycarbonyl)benzoic acid. (ii) converts the free to (ester untouched). (iii) The amine converts to the N-methylamide (second equivalent takes up HCl). The ester remains, so the product is methyl 2-(methylcarbamoyl)benzoate.
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