which isomer, 4-bromonitrobenzene or 2-bromonitrobenzene, will elute from a sili

Question

which isomer, 4-bromonitrobenzene or 2-bromonitrobenzene, will elute from a silica gel chromatography column first, and what physical property accounts for this order? which isomer, 4-bromonitrobenzene or 2-bromonitrobenzene, will elute from a silica gel chromatography column first, and what physical property accounts for this order? which isomer, 4-bromonitrobenzene or 2-bromonitrobenzene, will elute from a silica gel chromatography column first, and what physical property accounts for this order?

Explanation / Answer

Elution in silica gel chromatography column of a compound is polarity dependent. Since 4-bromonitrobenzene is less polar due to the electron withdrawing effects of the NO2 and Br directly in resonance with each other on the ring, it will move faster on the column and would be the first to elute out. On the other hand, 2-bromonitrobenzene is slightly more polar than the above compound and would be the last compound to be eluted from the column.

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