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Why is NH(2) group of aniline acetylated...

Why is `NH_(2)` group of aniline acetylated before carrying our nitration

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Due to the strong activating effect of `NH_(2)` group, aromatic amines readily undergo ele3ctrophilic substitution reactions and it is difficult to stop the reaction at the monosubstitution stage. Usually the reaction occurs to give 2,4,6-trisubstituted amines. for example, aniline on treatment with bromine water gives 2,4,6-tribromoaniline.
If, however, we wish to stop the reaction at the monosubstitution stage, the activating effet of the `-NH_(2)` group is reduced by acetylation. the acetyl group being electron-withdrawing attracts the lone pair of electrons on the N-atom towards itself. as a result, the lone pair of electrons on the N-atom is not exclusively available for donation to the benzene ring and hence the activating effect of the -`NH_(2)` group is reduced. this method is known as protection of the amino group by acetylation and can be used to stop the reaction at the monosubstitution stage by preventing the formation of di-and trisubstitution products. For example, acetylation of aniline gives acetanilide. bromination of acetanilide with `Br_(2)//CH_(3)COOH` followed by acid hydrolysis gives p-bromoaniline as the major products. Similarly, nitration of acetanilide with a mixture of conc. `HNO_(3)+conc.H_(2)SO_(4)` followed by acid hydrolysis gives pnitroaniline as the major product.
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PRADEEP-ORGANIC COMPOUNDS CONTAINING NITROGEN-NCERT EXEMPLAR PROBLEMS WITH ANSWERS, HINTS AND SOLUTIONS (SHORT ANSWER QUESTIONS)
  1. What is the role of HNO(3) in the nitrating mixture used for nitration...

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  2. Why is NH(2) group of aniline acetylated before carrying our nitration

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  3. What is the product when C(6)H(5)CH(2)NH(2) reacts with HNO(3)?

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  4. What is the best reagent to convert nitrile to primary amine

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  5. Give the structure of 'A' in the following reaction < img src="https:/...

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  6. What is Hinsberg reagent?

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  7. Why is benzene diazonium chloride not stored and is used immediately a...

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  8. Why does acetylation of - NH2 group of aniline reduce its activity eff...

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  9. Explain why MeNH(2) is stronger base than MeOH ?

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  10. What is the role of pyridine in the acelation reaction of amines?

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  11. Under the reaction condition (acidic, basic) the coupling reaction of ...

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  12. Predict the product of reaciton for aniline with bromine in non-polar...

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  13. Arraange the following compounds in increasing order of dipole moment?...

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  14. What is the structure and IUPAC name of the compound, allyl amine?

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  15. Write down the IUPAC name of

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  16. A compound Z with molecular formula C(3)H(9)N reacts with C(6)H(5)SO(2...

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  17. A primary amine, RNH(2) can be reacted with CH(3)-X to get secondary a...

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  18. Complete the following reaction

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  19. Why is aniline soluble in aqueous HCl?

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  20. Suggest a route by which the following conversion can be accomplished.

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