Which compound exhibits maximum dipole moment among the following ?
Show Hint
- Nitrobenzene (benzene ring bearing only one \(\mathrm{NO_2}\) group)
- para-Nitroaniline (\(\mathrm{NO_2}\) and \(\mathrm{NH_2}\) at positions 1 and 4 of the benzene ring)
- meta-Nitroaniline (\(\mathrm{NO_2}\) and \(\mathrm{NH_2}\) at positions 1 and 3 of the benzene ring)
- ortho-Nitroaniline (\(\mathrm{NO_2}\) and \(\mathrm{NH_2}\) at positions 1 and 2 of the benzene ring)
The Correct Option is B
Solution and Explanation
Para-nitroaniline: the -NH2 group pushes electrons into the ring (+R, +M), and -NO2 pulls them out (-R, -I); push and pull are along the same axis, so the group moments and the resonance charge transfer reinforce each other. mu is about 6.2 D, the largest.
Meta isomer: the two group moments are at 120 degrees and partially cancel, no direct conjugation; mu about 4.9 D.
Ortho isomer: the group moments at 60 degrees combine but intramolecular hydrogen bonding and steric/field effects reduce the net value; mu about 4.3 D.
So the largest dipole moment is that of p-nitroaniline.
Answer: (2) para-nitroaniline
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