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प्रश्न
Why does acetylation of –NH2 group of aniline reduce its activating effect?
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उत्तर
Direct nitration of aniline is not possible on account of oxidation of –NH2 group. However, nitration can be carried after protecting the –NH2 group by acetylation to give acetanilide which is then nitrated and finally hydrolysed to give o- and p-nitroanilines.
The acetyl group being electron-withdrawing attracts the lone pair of electrons of the N-atom towards carbonyl group.
As a result, the activating effect –NH2 group is reduced i.e., the lone pair of electrons on nitrogen is less available for donation to benzene ring by resonance. Therefore, activating effect of –NHCOCH3 group is less than that of –NH2 group.
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संबंधित प्रश्न
Illustrate the following reaction giving suitable example in each case: Diazotisation
Write equations of the following reactions:
Acetylation of aniline
Why is aniline soluble in aqueous HCl?
How will you carry out the following conversions?
p-toluidine diazonium chloride `→` p-toluic acid
A colourless substance ‘A’ \[\ce{(C6H7N)}\] is sparingly soluble in water and gives a water soluble compound ‘B’ on treating with mineral acid. On reacting with \[\ce{CHCl3}\] and alcoholic potash ‘A’ produces an obnoxious smell due to the formation of compound ‘C’. Reaction of ‘A’ with benzenesulphonyl chloride gives compound ‘D’ which is soluble in alkali. With \[\ce{NaNO2}\] and \[\ce{HCl}\], ‘A’ forms compound ‘E’ which reacts with phenol in alkaline medium to give an orange dye ‘F’. Identify compounds ‘A’ to ‘F’.
Predict the reagent or the product in the following reaction sequence.
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Which of the following is true characteristic feature of aniline?
Major Product In the above chemical reaction, intermediate "X" and reagent/condition "A" are:
Aniline dissolved in dilute HCl is reacted with sodium nitrate at 0 °C. This solution was added dropwise to a solution containing equimolar mixture of aniline and phenol in dil. HCl. The structure of the major product is:
Identify A and B for the following reaction:
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Aniline to benzene diazonium chloride.
Given below are two statements:
Statement I: Benzenediazonium salt is prepared by the reaction of aniline with nitrous acid at 273-278 K. It decomposes easily in the dry state.
Statement II: Insertion of iodine into the benzene ring is difficult and hence, iodobenzene is prepared through the reaction of benzenediazonium salt with KI.
In the light of the above statements, choose the most appropriate answer from the options given below:
