E2 Stereospecific

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

Stereospecific E2 eilimination

Note the spatial relationship of the two phenyl groups leading to Z- and E-alkenes.

Examine the animated energy plots of S,R-Diastereoisomer and R,R-Diastereoisomer to determine the relative energies of the anti-periplanar conformations required for E2 elimination and hence understand the rate difference.

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