JEE MainChemistryHydrocarbons
An aromatic compound X undergoes Birch reduction using sodium in liquid ammonia and ethanol to produce 1-methoxy-4-methylcyclohexa-1,4-diene as the major product. The IUPAC name of the reactant X is:
Options
- A2-Methoxytoluene
- B4-Methoxytoluene
- C3-Methoxytoluene
- DMethoxybenzene
Correct answer
B. 4-Methoxytoluene
Step-by-step solution
In Birch reduction, electron-donating groups (EDGs) like - OCH ₃ and - CH ₃ direct the reduction such that the carbons bearing these groups remain sp^2 hybridized (i.e., they remain part of the double bonds). The product is given as 1-methoxy-4-methylcyclohexa-1,4-diene. In this structure, both the methoxy group at C1 and the methyl group at C4 are attached to sp^2 hybridized carbons. For both EDGs to remain on the double bonds of an isolated 1,4-diene system, they must be positioned para (1,4) to each other on the