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12 grade chemistry others

Give reasons for the following.Acetylation of aniline reduces its activation effect.

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1 Year agoGrade
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1 Year ago

The acetylation of aniline, which involves the substitution of an acetyl group (-COCH3) for a hydrogen atom on the amino group (-NH2) of aniline, reduces its activation effect due to several reasons:

Electron-withdrawing effect: The acetyl group is electron-withdrawing due to the presence of the carbonyl group. This means it withdraws electron density from the amino group, making it less electron-rich. Since the activation effect of aniline arises from the lone pair of electrons on the amino group, reducing its electron density diminishes its activating ability.

Decreased nucleophilicity: The acetylation reaction involves the formation of a new bond between the amino group and the acetyl group, which reduces the availability of the lone pair of electrons on the nitrogen atom for participation in reactions. This reduced nucleophilicity decreases the ability of aniline to activate other groups in subsequent reactions.

Steric hindrance: The introduction of the bulky acetyl group can lead to steric hindrance, particularly in certain reaction environments. This steric hindrance may interfere with the ability of aniline to approach other reagents or substrates effectively, thereby reducing its activation effect.

Resonance delocalization: Aniline exhibits resonance stabilization due to the delocalization of electrons between the amino group and the benzene ring. Acetylation disrupts this resonance delocalization to some extent, reducing the overall stability of the molecule and hence its activation effect.

Overall, acetylation of aniline decreases its activating ability primarily due to the electron-withdrawing nature of the acetyl group, decreased nucleophilicity, steric hindrance, and disruption of resonance stabilization.




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