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JEE Advanced · 2016 · 22 May 2016 · Paper 2 · Compounds Containing Nitrogen

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Treatment of compound O with gave P, which on heating with ammonia gave Q. The compound Q on treatment with produced R. On strong heating, Q gave S, which on further treatment with ethyl 2-bromopropanoate in the presence of KOH followed by acidification, gave a compound T.

The compound R is
  1. (A)(see structure)
    ✓ Correct
  2. (B)(see structure)
  3. (C)(see structure)
  4. (D)(see structure)

Answer: (A)

Solution

Compound O (o-diethylbenzene) is oxidized by to phthalic acid (P). Heating with ammonia converts it to phthalimide (Q). The Hofmann bromamide degradation () converts the imide to o-phenylenediamine (R), which is structure (A).

JEE Advanced · 2016 · 22 May 2016 · Paper 2 · Single correct option

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