How to Predict the Major Product of Dehydration of an Alcohol - Part 3

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 reactions:



Click/tap to enlarge the image

Solution infographic:



Click/tap to enlarge the image

E1 = Elimination unimolecular

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

References:

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

(2)    Wikipedia Contributors. Elimination reaction. Wikipedia.

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

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

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

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