Name: Hunsdiecker Reaction
Uploaded: 2019-07-19
Duration: 2 min 54 s
Description: The Hunsdiecker reaction is a name reaction in organic chemistry whereby silver salts of carboxylic acids react with a halogen to produce an organic halide.

Question

Although chlorine is an electron-withdrawing group, yet it is ortho-para directing in electrophilic aromatic substitution reactions, why?

Accepted Answer

Chlorine withdraws electrons through the inductive effect and releases electrons through resonance. Through inductive effect, chlorine destabilises the intermediate carbocation formed during the electrophilic substitution.

Through resonance, halogen tends to stabilise the carbocation and the effect is more pronounced at ortho- and para- positions. The inductive effect is stronger than resonance and causes net electron withdrawal and thus causes net deactivation. The resonance effect tends to oppose the inductive effect for the attack at ortho- and para positions and hence makes the deactivation less for ortho- and para attack. Reactivity is thus controlled by the stronger inductive effect and orientation is controlled by the resonance effect.

Although chlorine is an electron-withdrawing group, yet it is ortho-para directing in electrophilic aromatic substitution reactions, why?

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