Elimination – E2 Stereospecific from diastereoisomers

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.

 

 

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