How to Predict the Major Product of Dehydration of an Alcohol - Part 2

Alcohol dehydration is an important reaction in organic chemistry as it opens the possibility of numerous derivatives.


Regiochemistry is reagent dependent. Concentrated sulfuric acid promotes E1 elimination; however, may trigger a rearrangement via hydride/alkyl shift, ring expansion/contraction as it involves carbocation intermediate(s).

Question:

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



Click/tap to enlarge the image

Solution infographic:



Click/tap to enlarge the image

E1 = Elimination unimolecular

How helpful is the infographic❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

NOTE: Post updated since published

References:

(1)    Rearrangement reaction. Wikipedia. https://en.wikipedia.org/wiki/Rearrangement_reaction.

(2)    Wikipedia Contributors. Elimination reaction. Wikipedia.

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

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