How to Predict where an Electrophilic Aromatic Substitution May Occur in a Ring – Part 6

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 recall 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 to enlarge the image

Solution infographic:



Click to enlarge the image

If two deactivating groups compete with each other in the same (or different) ring in the same compound, the deactivating group with a +M effect wins for substitution. A less sterically hindered position is preferred for substitution as well.

What's elegant about the EAS chemistry❓ Let Chemaficionado know 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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