University13 min

SN1, SN2, E1, E2: choosing the mechanism

Four criteria — substrate, reagent, solvent, temperature — to predict the mechanism for a haloalkane, then the stereochemistry and the major alkene.

The essentials

1

SN2: one step, inversion

A concerted mechanism: the nucleophile attacks opposite the leaving group. Rate law v=k[RX][NuX]v = k[\ce{RX}][\ce{Nu-}], second order. Stereochemistry: Walden inversion, e.g. (R)-2-bromobutane + HOX+\ \ce{HO-} gives (S)-butan-2-ol. Reactivity: methyl > primary > secondary; a tertiary substrate does not react this way, its rear face is hindered.
2

SN1: a carbocation, racemisation

Members only

3

E2: concerted, anti-periplanar

Members only

4

E1: the competitor of SN1

Members only

5

Nucleophile or base? The solvent

Members only

ƒWrite my own sheetOr start from a blank page: rewriting a concept in your own words is how it sticks.