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JEE Advanced2023Paper 1CHEM-II
Q.

In the given reaction scheme, P is a phenyl alkyl ether, Q is an aromatic compound; R and S are the major products.

The correct statement about S is

  1. A

    It primarily inhibits noradrenaline degrading enzymes.

  2. B

    It inhibits the synthesis of prostaglandin.

  3. C

    It is a narcotic drug.

  4. D

    It is ortho-acetylbenzoic acid.

Solution

Identifying intermediates. The phenyl alkyl ether P on cleavage with HI gives phenol (Q) and an alkyl iodide. Phenol treated with NaOH gives sodium phenoxide which, on Kolbe-Schmitt carboxylation with CO followed by acidification, gives salicylic acid (2-hydroxybenzoic acid) as R.

Step R S. Acetylation of the phenolic OH of salicylic acid with acetic anhydride (and acid workup) gives acetylsalicylic acid, commonly known as aspirin.

Mode of action of aspirin. Aspirin is a non-narcotic analgesic that inhibits the cyclo-oxygenase enzymes responsible for the biosynthesis of prostaglandins. Hence option (B) correctly describes S. Aspirin is the ortho-acetoxy (not acetyl) benzoic acid, so option (D) is incorrect.

Answer: (B).

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