What happens when aniline is acetylated?

Aniline reacts with acetic anhydride to form Acetanilide by nucleophilic substitution reaction and the reaction is called acetylation. In this reaction, aniline acts as the nuclepohile and acyl (CH3CO-) group from acetic anhydride acts as the electrophile.

Which reagent should be used for acetylation of aniline?

– Acetic anhydride is the modest isolable anhydride of a carboxylic acid and is extensively used as a reagent in organic synthesis. – The acetylation of aniline generally takes place in the presence of Zinc dust. – Zinc dust is used in the chemical reaction to prevent the oxidation of aniline.

What is obtained on acetylation of aniline?

N-acetyl amino benzene.

Why acetylation of aniline is done?

Why is group of aniline acetylated before carrying out nitration? Answer: Due to the strong activating effect of group, aromatic amines readily undergo electrophilic substitution reactions and it is difficult to stop the reaction at the monosubstitution stage. For example, acetylation of aniline gives acetanilide.

Why is Acetanilide used instead of aniline?

Transcribed image text: Acetanilide is used instead of aniline for the nitration because aniline has an unwanted side reaction. The product of the third reaction is a diazonium salt, which is not isolated but is used immediately.

Which is more basic than aniline?

Benzylamine C6H5 – NH2 is more basic than aniline because benzyl group C6H5CH2 is electron donating group due to +I effect. So, it is able to increase the electron density of N of -NH2 group.

Which reagents is used for acetylation?

Silica sulfuric acid as a mild and efficient reagent for the acetylation of alcohols in solution and under solvent-free conditions.

Why is acetanilide used instead of aniline?

Is aniline a good nucleophile?

Aniline is not a good nucleophile because the lone pair of electrons of nitrogen are resonance stabilized by the benzene ring. Anilinium chloride is also not a good nucleophile, and actually acts as an electrophile. So rather than donating electrons, it accepts. Bromination of aniline would result in a trisubstitution.

How do you convert aniline to acetanilide?

Acetanilide is prepared from aniline when it reacts with acetic anhydride/glacial acetic acid in the presence of zinc dust. A mixture of aniline, glacial acetic acid, acetic anhydride and zinc dust is refluxed under anhydrous condition and then poured the mixture into ice cold water to get acetic anhydride precipitate.

Which is more basic aniline or methylaniline?

Aniline is an aromatic amine. The basicity of the aromatic amine is depending upon the availability of the lone pair. In case of aniline due to conjugation the lone pair density is less than that of methylamine. Due to this reason, aniline is less basic than methylamine.

Why is aniline a weak base?

Traditionally, the weak basicity of aniline is attributed to a combination of inductive effect from the more electronegative sp2 carbon and resonance effects, as the lone pair on the nitrogen is partially delocalized into the pi system of the benzene ring.

How to make acetylation of aniline hydrochloride?

Measure out 0.6 mL of acetic anhydride and prepare a solution of 530 mg of sodium acetate in 3 mL of water. Add the acetic anhydride to the solution of aniline hydrochloride in water, mix by swirling, and immediately add the sodium acetate solution. The solution becomes white as acetanilide precipitates.

How to make acetanilide from 2 mL aniline?

Add 2 mL aniline (density 1.02 g cm -3) and swirl the mixture. If the solution is coloured, add a small amount of decolourising charcoal, swirl the flask for about one minute, and filter off the carbon using a fluted filter paper (see the Appendix). In a separate container dissolve 3 g sodium acetate in 10 mL water.

How to prepare acetanilide from aqueous sodium acetate?

Swirl to effect dissolution and add the aqueous sodium acetate quickly. Swirl the flask a couple of times and set it in an ice-bath for 20 min. Filter, with suction, the crystals of the amide formed and wash with a small amount of ice-cold water. Continue to apply suction to the Büchner funnel for a few minutes.

How to dissolve acetic acetate in a water bath?

In a separate container dissolve 3 g sodium acetate in 10 mL water. Warm the anilinium chloride solution to 50°C on a water bath and add 3 mL acetic anhydride (density 1.08 g cm -3 ). Swirl to effect dissolution and add the aqueous sodium acetate quickly.