Toluene is subjected to Birch reduction using sodium in liquid ammonia and ethanol to yield a major product P . Product P is then treated with ozone followed by zinc dust and water to yield two organic products Q and R . The IUPAC names of

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Toluene is subjected to Birch reduction using sodium in liquid ammonia and ethanol to yield a major product P . Product P is then treated with ozone followed by zinc dust and water to yield two organic products Q and R . The IUPAC names of Q and R are:

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Correct answer: C. Propanedial and 3-oxobutanal

The methyl group in toluene is an electron-donating group (EDG). During Birch reduction, EDGs direct the reduction such that the carbon atom bearing the substituent remains sp^2 hybridized. Thus, the Birch reduction of toluene yields 1-methylcyclohexa-1,4-diene as the major product P . The double bonds in P are located at the C1-C2 and C4-C5 positions. Next, P undergoes reductive ozonolysis ( O ₃ followed by Zn/H ₂ O ). This cleaves the two double bonds: 1. Cleavage of the C4=C5 and C1=C2 bonds breaks the ring into

Toluene is subjected to Birch reduction using sodium in liquid ammonia and ethanol to yield a major product P . Product P is then treated with ozone followed by zinc dust and water to yield two organic products Q and R . The IUPAC names of Q and R are:

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