Interpretation:
The observation that the N,N,N-trimethylammonium group –N(CH3)3, though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained.
Concept introduction:
In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar.
If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles.
The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid.
To explain:
The observation that the N,N,N-trimethylammonium group –N(CH3)3, though a meta directing deactivator does not exhibit electron withdrawing resonance effect.
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Chapter 16 Solutions
Organic Chemistry
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning