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Substitution and Elimination Reactions

Substitution and Elimination Reactions - Deciding Between...

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Unformatted text preview: Deciding Between Different Substitution and Elimination Reactions Chem 112A - Fall 2010 These summaries and fow charts are meant to help you decide which type oF reaction a given nucleophile/elec- trophile pair will undergo (iF any). In many cases multiple reactions can occur, but the major pathway is likely to be the one that is listed on the charts that Follow. Please note that these reactions can be unpredictable, so this simple guide might be misleading in many real-liFe cases! To use it, ¡rst decide the Following: 1. Is the electrophilic carbon a methyl, primary, secondary, or tertiary center? 2. Is a good nucleophile present (e.g. HS- , RS- , I- , Br- , Cl- , - CN, N 3- , NH 3 , NRH 2 , or maybe F- , HO- , RO- , or RCO 2- )? 3. Is the nucleophile strongly basic and sterically hindered (e.g. tert-butoxide or ( i Pr) 2 N- )? 4. Is the solvent polar and protic (e.g. H 2 O, MeOH, or HOAc) or polar and aprotic (DMSO, DM¢, CH 3 CN, or TH¢)? In general, none oF these reactions work well in nonpolar solvents (like diethyl ether and hexanes).TH¢)?...
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Substitution and Elimination Reactions - Deciding Between...

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