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JEE Main · 2019 · 10 Apr 2019 · Shift 2 · Haloalkanes and Haloarenes

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The major product obtained in the given reaction is
  1. (A)(see structure)
  2. (B)(see structure)
  3. (C)(see structure)
  4. (D)(see structure)
    ✓ Correct

Answer: (D)

Solution

Heating the allyl aryl ether sets off a Claisen rearrangement, a -sigmatropic shift that delivers the allyl group to the ring carbon ortho to the oxygen and regenerates the phenol. The freed double bond of that ortho-allyl phenol is then positioned to cyclise back onto the oxygen, closing a six-membered oxygen-containing ring fused to the benzene ring and giving the chromane-type product.

JEE Main · 2019 · 10 Apr 2019 · Shift 2 · Single correct option

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