Chemistry - GOC Question with Solution | TestHub

ChemistryGOCRESONANCE AND MESOMERIC EFFECTMedium2 minQB
ChemistryMediumsingle choice

Arrange the ortho (I), meta (II) and para (III) nitrobenzyl carbocations in decreasing order of stability.

(I) structure

(II) structure

(III) structure

Options:

Answer:
A
Solution:

NO₂ is a -I and -M group, so it destabilises a benzylic cation. The -M effect works only from the ortho and para positions, so the meta isomer (only -I) is the least destabilised.

Between ortho and para, the -I effect falls with distance, so it hurts the ortho cation more.

Order : II III I.

Stream:JEESubject:ChemistryTopic:GOCSubtopic:RESONANCE AND MESOMERIC EFFECT
⏱ 2mℹ️ Source: QB

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