Question

What is obtained when Benzoyl Chloride reacts with Aniline in presence of Sodium Hydroxide?
(A) Benzoic acid
(B) Benzanilide
(C) Acetanilide
(D) Azobenzene

Answer 1

Hint: Nucleophilic N-atoms in Aniline can attack electrophilic atoms of Benzoyl Chloride and give a reaction. The Name of this reaction is Schotten-Baumann reaction.

Complete Step-by-Step Solution:

As shown in the mechanism, the N-atom of aniline is nucleophilic and it attacks the carbonyl carbon of Benzoyl chloride. Carbonyl carbon is often a preferred place for nucleophilic attack.
- Then Proton is lost and consequently, Chlorine anion is removed from the molecule to give neutral product Benzanilide.
- We can see that HCl is also formed during the reaction. So presence of Sodium hydroxide not only catalyses the reaction but also neutralizes the effect of acid formed in the reaction.
- So, option (B) Benzanilide is correct.

Additional Information:
- This reaction involves formation of a C-N bond. We can categorize this reaction to Condensation Reactions.
-A Condensation reaction is a type of a reaction in which two molecules combine to give a product and small neutral molecules like water, Ammonia etc…
- Benzanilide is used as Fungicide and Pesticide as well.
- In this Schotten-Baumann reaction, Pyridine can also be used as a catalyst in place of Sodium hydroxide.

Note:
- Do not get confused between Benzoyl chloride, Benzyl Chloride, Benzal Chloride and Benzo Chloride whose structures are as shown below.


Here no suitable conditions or reagents are present for electrophilic aromatic substitution, So, do not consider it.