CHM136H1 Study Guide - Final Guide: Protic Solvent, Sn2 Reaction, Lewis Acids And Bases
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CHM136H1 Full Course Notes
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Document Summary
Oh- attacks partially positive c (from opposite side of leaving group: transition state. Rate depends on concentration of nucleophile and substrate: second-order reaction, rate = k [nu-] [substrate, both participate in rate-limiting step (step 1) Takes place in single step ~ no intermediates. Back-side attack ~ inversion con guration: nucleophile repels h ~ h ips to other side when lg leaves, stereochemistry inverts. Only occurs with relatively unhindered halides: methyl halides, primary halides, simple secondary halides. Hindered halides - very slow/unreactive: tertiary, branched secondary, vinylic (c=c), aryl halides - nu- has to go through c=c plane. Nucleophilicity - roughly same as basicity: nucleophilicity. Kinetic property - rate that nucleophile attacks compound: basicity. Thermodynamic property - position of equilibrium in acid-base reaction. Better nucleophile = faster reaction: anion > nucleophile than neutral conjugate, more polarizable orbitals (i >br > cl, s > o, stronger bases. Better lg = faster reaction: better lg. More stable anions: usually conjugate bases of strong acids.
