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The decreasing order of reactivity towards electrophilicsubstitution of the following compounds is A benzene B chlorobenzene C nitrobenzene D methylbenzene Please explain how the reactivity depends

The decreasing order of reactivity towards electrophilicsubstitution of the following compounds is
A benzene
B chlorobenzene
C nitrobenzene
D methylbenzene
 
Please explain how the reactivity depends

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2 Answers

Arun
25750 Points
5 years ago

from left to right: phenol, toluene, benzene, fluorobenzene, and nitrobenzene.

From left to right, the amount of electron donation into the ring (activating the ring towards EAS) decreases. 

  • OH is a σ donor (its HOMO is a σ bonding orbital), thereby activating the ring strongly.
  • CH3 donates via hyperconjugation (from its C−H bonds), thereby activating the ring weakly.
  • F is a decent π donor (filled p nonbonding orbitals) but is a good EWG, thereby deactivating the ring weakly.
  • NO2 is a very strong EWG, thereby deactivating the ring strongly.

Therefore, from left to right, we have most to least reactive towards EAS.

Arun
25750 Points
5 years ago
I am attaching the image fpr the above solution which I forgot to attach.
 
hope it helps
 
In case of any difficultybplease feel free to ask
 

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