Q.

The substituents which are deactivating but ortho para directing in aromatic substitutions is

 -NO2,-CHO,-F,-Cl,-Br,-OH,-COCl,-NH2,-CN

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answer is 3.

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Detailed Solution

  • When adding at the ortho- or para-position during electrophilic aromatic substitution, a carbocation intermediate with a resonance form that has a carbocation next to the directing group is produced. 
  • The lone pair of halogens like fluorine, chlorine, and bromine can generate a pi-bond with the nearby carbocation. Halogens are generally deactivating, but this "pi donation" aids in stabilizing the transition state that results in ortho- or para-products, which is why they are ortho, para- directors. 

Therefore, the substituents which are deactivating are fluorine, chlorine, and bromine.

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The substituents which are deactivating but ortho para directing in aromatic substitutions is -NO2,-CHO,-F,-Cl,-Br,-OH,-COCl,-NH2,-CN