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10 MECHANISMS

Substitution & Elimination

SN2 Inversion

SN2 Inversion

Backside attack inverts the stereocenter in one step.

E2 of Alkyl Halides

E2 of Alkyl Halides

Concerted anti-periplanar loss of H and X gives an alkene.

SN1 Solvolysis

SN1 Solvolysis

The substrate ionizes to a carbocation, then solvent attacks.

E1 Elimination

E1 Elimination

A carbocation forms, then loss of a beta-proton gives the alkene.

SN1 Stereochemistry

SN1 Stereochemistry

The planar cation is attacked from both faces, giving racemic product.

SN2 with Tosylate

SN2 with Tosylate

A tosylate leaving group is displaced with inversion.

SN1 with Rearrangement

SN1 with Rearrangement

A hydride or alkyl shift builds a more stable cation.

E1 with Rearrangement

E1 with Rearrangement

The cation rearranges before eliminating to an alkene.

SN2 of Alcohols

SN2 of Alcohols

A protonated alcohol is displaced by halide via SN2.

SN1 of Alcohols

SN1 of Alcohols

A protonated alcohol ionizes, then halide traps the cation.