How to Predict where a Reaction May Occur in a Ring Compound – Part 1

Reactions in organic chemistry are diverse, ain’t they?


An organic compound may typically undergo addition (all in, none out), elimination (all out, none in), substitution (some out, some other in) or rearrangement (change in constitution) reaction. There are many sub-types.

Addition (A) or substitution (S) can be electrophilic (E) or nucleophilic (N) like AE, SN, AN or SE. Substitution or elimination (E) can be unimolecular (1) or bimolecular (2) like SN1, SN2, E1 or E2.

The reaction can be in the ring or in the side-chain depending on the reagent used (reagent dependent regiochemistry).

A rearrangement may be triggered via hydride/alkyl shift, or ring expansion/contraction.

Question:

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



Click/tap to enlarge the image

Solution infographic:



Click/tap to enlarge the image

Reaction riddles❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

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

‌(2)    Graham, T. W.; Fryhle, C. B.; Snyder, S. A. Organic Chemistry.; Hoboken, Nj John Wiley Et Sons, Inc, 2016.

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

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

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

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