SN1_SN2_E1_E2 - N 2 Yes No E2 S N 2 / E2 No Rxn Key...

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Flow Chart for Determining S N 1/S N 2/E1/E2 Reactions If you are given some overall transformation, you should be able to decide which mechanistic pathway is most reasonable by following the logic outlined below. Does the substrate have a good leaving group? No Yes Is the nucleophile / base strong? No Yes What is the nature of the substrate? Is the reagent a better nucleophile or a better Bronsted base? 1 o 2 o 3 o No Rxn S N 1/E1 S N 1/E1 Nucleophile Base What is the nature of the substrate? What is the nature of the substrate? 1 o 2 o 3 o 1 o 2 o 3 o E2 S N 2 Is the base bulky? What is the nature of the solvent? S N 2 S N 1 Polar Protic Polar Aprotic S N 1 S
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Unformatted text preview: N 2 Yes No E2 S N 2 / E2 No Rxn Key Similarities and Differences in S N 1/S N 2/E1/E2 Substitutes LG with a Nuc Polar solvents S N 1 S N 2 E1 E2 Weak nucleophile Strong nucleophile Stereochemical inversion Stereochemical recemization Aprotic solvent Lower temp Higher temp 3 o > 2 o > 1 o Polar, protic solvents 1 o > 2 o > 3 o Unimolcular RDS Good LG Weak Nuc / Base Bimolecular RDS Polar, aprotic solvents Srong Nuc / Base Eliminates H-LG to give a double bond Zaitsev products when possible Weak, hindered base Strong base Antiperiplanar geometry...
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This note was uploaded on 07/16/2008 for the course CH 310M taught by Professor Iverson during the Spring '05 term at University of Texas.

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SN1_SN2_E1_E2 - N 2 Yes No E2 S N 2 / E2 No Rxn Key...

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