Aniline does not react with methyl chloride in the presence of anhydrous AlCl3 catalyst.

Question 20:Aniline does not react with methyl chloride in the presence of anhydrous AlCl3 catalyst.

The correct answer is – Aniline is an aromatic primary amine that can undergo electrophilic aromatic substitution reactions, but it does not react with methyl chloride in the presence of anhydrous aluminum chloride (AlCl3) catalyst. The reason for this is that the reaction conditions for the Friedel-Crafts alkylation of aniline with alkyl halides are too harsh for aniline due to its basic nature. Aniline contains an amino group (-NH2) that is more nucleophilic than the aromatic ring, making it susceptible to protonation by the AlCl3 catalyst. This protonation leads to the formation of anilinium ion, which is a powerful electrophile that can react with the methyl chloride to form N-methyl aniline. However, the strong acid conditions needed for the protonation of aniline and the reaction with alkyl halides can lead to side reactions, such as N-alkylation and over-alkylation. To prevent these unwanted side reactions, alternative methods can be used to introduce an alkyl group onto the aniline molecule, such as acylation or nitration followed by reduction. These methods do not require the use of strong acid catalysts, making them more suitable for the synthesis of substituted anilines.