How to Predict where an Electrophilic Aromatic Substitution May Occur in a Ring – Part 7

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 bromination. Let's keep in mind that bromination may happen in a ring or in the side-chain depending on the reagent.

Question:

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



Click/tap to enlarge the image

Solution infographic:



Click/tap to enlarge the image

If a strongly activating group competes with a weakly activating group in the same (or different) ring in the same compound, the strongly activating group wins for substitution despite steric effect.

Eccentric EAS chemistry❓ 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)    Wikipedia Contributors. Halogenation. Wikipedia. https://en.wikipedia.org/wiki/Halogenation#Bromination.

‌(3)    Electrophilic aromatic directing groups. Wikipedia. https://en.wikipedia.org/wiki/Electrophilic_aromatic_directing_groups.

‌‌(4)    Chouhan, M. S. Advanced Problems in Organic Chemistry for JEE, 11th Ed.

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