How to Predict where an Electrophilic Aromatic Substitution May Occur in a Ring – Part 3

An organic reaction in which an atom attached to an aromatic system (usually hydrogen) is substituted by an electrophile is referred to as electrophilic aromatic substitution (SEAr or EAS).


One of the most important EASs is halogenation. If Bromine water is added to Aniline, a multi-substituted product (2,4,6-derivative) is obtained as Aniline is a strongly activating group (the same happens to Phenol). To generate the mono-substituted product, a protection, say, an acyl group is required.

Question:

Predict the major product(s) of the following reaction:



Click/tap to enlarge the image

Solution infographic:



Click/tap to enlarge the image

Motivated by EAS❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

(1)    Wikipedia Contributors. Electrophilic aromatic substitution. Wikipedia. https://en.wikipedia.org/wiki/Electrophilic_aromatic_substitution.

(2)    Chouhan, M. S. Advanced Problems in Organic Chemistry for JEE, 11th Ed.

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