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JEE Main levelSingle correct optionDifficulty 2 of 3ro170

Anisole (methoxybenzene) is reduced with Na in liquid and ethanol. The major product is

  1. Amethoxycyclohexane
  2. B1-methoxycyclohexa-1,4-diene
  3. C1-methoxycyclohexa-1,3-diene
  4. D3-methoxycyclohexa-1,4-diene

Answer: B

An electron-donating group such as OMe stays on a carbon that remains sp2, because the radical anion is protonated at positions that avoid placing negative charge next to the donor. The product is therefore the 1,4-diene in which C-1 bearing OMe is a double-bond carbon. The 3-methoxy isomer has OMe on an sp3 carbon, and the conjugated diene is not a Birch product.
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