How to Recognize Nucleophilic Substitution in an Aromatic Compound – Part 2

A nucleophilic substitution (SN) is a class of organic chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group (called the leaving group or LG) within another electron-deficient molecule (known as the electrophile) referred to as the substrate.


This may engage either a one- (1) or two-step (2) mechanism (unimolecular and bimolecular respectively).

Aromatic rings are usually nucleophilic, but some aromatic compounds do undergo nucleophilic substitution especially if o-,p-positions carry strong electron withdrawing groups (EWGs).

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



Click/tap to enlarge the image
Solution infographic:


Click/tap to enlarge the image

This is a nucleophilic substitution, SN2 (and electrophilic addition, AE) in the side chain of the aromatic ring only!

How is the combo of AE & SN2❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

(1)    Graham, T. W.; Fryhle, C. B.; Snyder, S. A. Organic Chemistry.; Hoboken, Nj John Wiley Et Sons, Inc, 2016.

(2)    Ncert. Chemistry : Textbook for Class XII - Part.II; National Council Of Educational Research And Training: New Delhi.

(3)    Brown, C.; Ford, M. Higher Level Chemistry, 2nd ed.; Pearson Education: Harlow, Essex, 2014.

‌(4)    Wikipedia Contributors. Nucleophilic substitution. Wikipedia. https://en.wikipedia.org/wiki/Nucleophilic_substitution.‌

(5)    Wikipedia Contributors. Electrophilic addition. Wikipedia. https://en.wikipedia.org/wiki/Electrophilic_addition.

‌(6)    Chouhan, M. S. Advanced Problems in Organic Chemistry for JEE, 11th Ed.

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