IMG_0005_NEW - Fall 2006 Chem 281 Decidinq between Sr1....

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Chem 281 Fall 2006 Decidinq between Sr1. Sr,r2. E1, E2 1. Consider solvent and base/nucleophile. . a good base/nucleophile indicates E2lSn2 (e.9. charge) note: (CH3[CONa in (CHg)3COH is still a is protic. . An aprotic solvent indicates E2|SN2 . if the solvent is protic and the base/nucleophile is poor reaction will proceed via SN1/E1 mechanism (e.9. H2O or (CHs)aCOH) the 2. Once you have decided whether the conditions favour E2|SN2 or Sru'1/E1 consider what type of carbon the leaving group is attached to' For E2iSr.r2 conditions: ' 1o (primarY) carbon favors SN2 . 3o (tertiary) carbon ONLY E2 . 2o (se co n d a vl :i,f"T ;:;""1 |;#fi f ft i[?*. .iE:". ; : ff J:]' :!'. n, NO xn favors Sr.r2 3. EliSnl conditions usually provide a mixture of products since the first step (RDS) is the same for both - though the more bulky the base/nucleophile the more El product will be formed orHER REACTIONS COVERED (OR TO BE COVERED) *you should know all mechanistic and experimental details
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This note was uploaded on 12/27/2011 for the course CHEM 281 taught by Professor Williams during the Fall '11 term at Simon Fraser.

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