The given question is to identify an example of an aromatic nucleophilic substitution reaction from the provided options. Let's analyze each option to determine the correct answer:
Gatterman Koch reaction: This is primarily an electrophilic aromatic substitution reaction used to introduce a formyl group (-CHO) into an aromatic ring. It doesn't involve nucleophilic substitution.
Chichibabin reaction: This is a classic example of an aromatic nucleophilic substitution reaction where a hydrogen atom on the aromatic ring (specifically pyridine) is substituted by an amino group (NH2), typically using sodium amide (NaNH2) in liquid ammonia. Hence, this matches the criteria for an aromatic nucleophilic substitution reaction.
Kolbe's reaction: Also known as Kolbe-Schmitt reaction, this is a carboxylation chemical reaction that converts phenols into salicylic acids. It involves an electrophilic aromatic substitution, not nucleophilic.
Friedel-Crafts reaction: This includes alkylation and acylation reactions which are examples of electrophilic aromatic substitution, where an aromatic compound is treated with a haloalkane or acyl chloride using a Lewis acid catalyst.
Based on the above analysis:
The correct answer is Chichibabin, as it is the only reaction among the options given that is an aromatic nucleophilic substitution reaction.
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