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JEE Main levelSingle correct optionDifficulty 2 of 3ro030

1,4-Dimethoxybenzene undergoes Birch reduction with Na, liquid and ethanol. The major product is

  1. A3,6-dimethoxycyclohexa-1,4-diene
  2. B1,4-dimethoxycyclohexa-1,4-diene
  3. C1,2-dimethoxycyclohexa-1,4-diene
  4. D1,4-dimethoxycyclohexane

Answer: B

Both donor groups prefer to remain on double-bond carbons. Reduction occurs at the ring positions ortho/meta to each OMe (C2 and C5), leaving C1=C6 and C3=C4 double bonds, i.e. 1,4-dimethoxycyclohexa-1,4-diene.
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