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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro178

1-Methoxy-4-methylbenzene is subjected to Birch reduction (Na, liquid , ethanol). The major product is

  1. A1-methoxy-4-methylcyclohexa-1,4-diene
  2. B1-methoxy-4-methylcyclohexane
  3. C1-methoxy-4-methylcyclohexa-1,3-diene
  4. D1-methoxy-4-methylcyclohexa-2,5-diene

Answer: A

Both OMe and CH3 are donor groups, so both prefer to stay on carbons that remain sp2. Hydrogen is therefore added at C-3 and C-6 and both substituents stay on double-bond carbons. This gives the 1,4-diene with substituents at C-1 and C-4. The 2,5-diene name would place both groups on sp3 carbons, which is the acceptor-group pattern.
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