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Unformatted text preview: Good Nucleophiles Strong Bases I Br Cl CN SH SR N 3 C CR OH OR NH 2 bulkier is less nucleophilic Reaction Examples Below are several examples of competition between the various reaction pathways. 2006 Gregory R . Cook page 1 Chem 341 North Dakota State University Br Na CN CN HMPA 1 subtrate Good nucleophile Aprotic polar solvent Br t-BuOK BuOH S N 2 E2 1 subtrate Good Base Protic polar solvent CH 3 CO 2 Na 2 subtrate Good nucleophile very weak base NaOEt S N 2 E2 2 subtrate Good Base some subst competes Br Br O O S N 2 O 80% 20% CH 3 CH 2 OH 3 subtrate Neutral Conditions Protic polar solvent NaOEt S N 1 3 subtrate Strong Base elim wins Br Br OH EtOH E1 20% 80% E2 97% OH HCl Cl racemic S N 1 OH Tos-Cl CN inversion S N 2 Et 3 N O Tos NaCN DMSO OH PBr 3 or SOCl 2 CN Et 3 N Cl (or Br) NaCN DMSO inversion S N 2 inversion S N 2 NOTE overall retention of configuration (2 inversions) 2006 Gregory R . Cook page 2 Chem 341 North Dakota State University...
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