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bart · organic chemistry II · day 03
day 03 · sn1 / sn2 · ≈ 90 minutes

nucleophilic substitution, slowly.

by the end of today you'll be able to look at a substrate, identify whether SN1 or SN2 is winning, and predict the product without guessing. we'll start with the kinetics, then build up to ambiguous cases.

rateSN2 = k [substrate][nucleophile]

SN2 is one step, concerted, and stereospecific — the nucleophile attacks the back side and the leaving group leaves in the same motion. That's why tertiary substrates lose: too crowded.

quick check ✦ 30 seconds
which of these is most likely SN1: 2-bromobutane, t-butyl bromide, or bromocyclohexane?