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JEE Main levelSingle correct optionDifficulty 2 of 3ro239

The compound shown is treated with Na in liquid with ethanol. Which structure is the major product?

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

Answer: D

The compound is toluene. The methyl group is electron donating and remains on a double-bond carbon in the Birch product, 1-methylcyclohexa-1,4-diene. The alternative with the methyl on an sp3 carbon corresponds to an electron-withdrawing substituent, and the 1,3-diene and cyclohexane are not the Birch outcome.
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