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NEET levelSingle correct optionDifficulty 1 of 3ro237

The compound shown is subjected to Birch reduction (, liquid , ethanol). Which structure is the major product?

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

Answer: B

The compound is anisole. In the Birch reduction an electron-donating group such as stays on an sp2 carbon of the 1,4-cyclohexadiene, giving 1-methoxycyclohexa-1,4-diene. The isomer with the donor on an sp3 carbon is the pattern for electron-withdrawing groups, the conjugated 1,3-diene is not the kinetic product, and cyclohexane is over-reduction.
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