Comparison of Substitution and Elimination Reactions

Comparison of Substitution and Elimination Reactions -...

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Unformatted text preview: Comparison of Substitution & El imination Mechanisms Property 3N1 v 3N2 E1 ”‘ E2 Rate Law == k[R—XJ_# = k R—X uc = k[R~X __ " __, kgR—XHfiése # of steps 2 1 a .2 W N 1 ., Intermediates» Carbocation None Carbonation > None RX 3 °>2°>1 °>Met Met >1°>2°33° 3°>2°> 1 °>Met 3°>2°>1°>Met leglogen >I>Br>Cl>F I>Br>Cl>F l>Br>Cl>F I>Br>ClT>F Solvents Protie Polar A . tic Protic _ Polar Aprotic Nucleophilel No effect Better Nucleo. No effect Better Base faster Base Faster reaction reaction Stereochernical Racemization Inversion None Stereoselective, results - stereos . ’ cific Stereochemistry None Back-side none Trans-coplz _gf reaction A " attack - gH—C-C-K Rearrangements Possible None Possible None 1,2—H shift &. 1,2-H shift & 13-31le shut 1,2—alk 1 shift Substingt‘igng Sni) A_‘_Substitution ”Elimination E2 Side—Regions Elimination El Notes : Tertiary alkyl halides favor elimination. Primary alkyl halide Elimination follows Saytzeff’ 5 Rule EXCEPT when Bulky base 01‘ R3NF. Most substituted alkene product is call Least substituted al Solvolysis : s favor substitution. ( (CH3)3CO' ) is used or le kene product is call SNl reaction in which the solvent i aving group is F ed the Saytzeff product. ed the Hoffman product. 5 the nucleophile. ...
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