Elimination – E2 Regioselective Elimination from Menthyl Chlorides to Menthenes A

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

Stereospecific E2 elimination

Stereospecific E2 eliminations – two diastereoisomeric chlorides Diastereoisomer A and Diastereoisomer B derived from menthol give two different regioisomers of alkene.
Manipulate the conformations to explore the arrangements of the protons and the chlorine. Are they anti-periplanar as required for E2?

Examine the animated energy plots of Diastereoisomer A and Diastereoisomer B to determine the relative energies of the anti-periplanar conformations required for E2 elimination.

J. F. Bunnett, Angew. Chemie Int. Ed. English, 1962, 1, 225–235.


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