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The E2 elimination, bimolecular reaction

This is a concerted (one-step) mechanism. The C=C bond begins to form at the same time as the C-H and C-X bonds begin to break. The reaction is second order (or bimolecular), as the rate depends on the concentration of the base and the alkyl halide. [Pg.73]

The elimination requires the alkyl halide to adopt an antiperiplanar shape (or conformation), in which the H and X groups are on the opposite sides of the molecule. (Synperiplanar conformation is when the H and X groups are on the same side of the molecule.) The antiperiplanar arrangement is lower in energy than the synperiplanar arrangement, as this has a staggered, rather than an eclipsed, conformation. [Pg.73]

The elimination is stereospecific, as different stereoisomers of the alkyl halide give different stereoisomers of the alkene. This is because the new Jt-bond is formed by the overlap of the C-H o-bond with the C-X o -bond. These orbitals must be in the same plane for the best overlap, and they become p-orbitals in the Jt-bond of the alkene. [Pg.73]

A different alkene stereoisomer is obtained from each diastereoisomer of the alkyl halide. [Pg.74]

For elimination in cyclohexanes, both the C-H and C X bonds must be axial. [Pg.74]


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