Discussion
The major products of the following reaction is :
Quinoline treated with HNO3/H2SO4.
Answer: A
The products are 5-nitroquinoline and 8-nitroquinoline.
In concentrated acid quinoline is protonated on nitrogen. The quinolinium ion's pyridine ring is strongly deactivated, so the nitronium ion attacks the benzene ring instead. Positions 5 and 8, the carbons next to the ring fusion, give the most stable cationic intermediates (each keeps the pyridinium ring intact and allows more resonance forms), so nitration gives a roughly equal mixture of 5- and 8-nitroquinoline.
Positions 3 and 4 are on the deactivated heterocyclic ring and are not attacked under these conditions, which rules out options C and D. Position 6 gives a less stabilised intermediate than 5, which rules out option B.
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