Lecture-14-Sub.pdf - CHEM 8A Lectures 14 15 A GENERAL...

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CHEM 8A Lectures 14 & 15 A GENERAL SUBSTITUTION REACTION A GENERAL ELIMINATION REACTION NUCLEOPHILES ELECTROPHILES Good Okay Poor Alkyl Halides, RX (Not aryl or vinyl) Activated Alcohols, ROH 2 , ROSCl, ROPBr 2 , ROTos *Add these to your N&E list* LEAVING GROUP CONSIDERATIONS (Same idea as considering the stability of a conjugate base) Good leaving groups: Bad Leaving Groups (Not leaving groups) Bigger is better! Neutral or resonance-stabilized leaving groups are good. SOLVENTS Polar, aprotic Polar, protic
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CHEM 8A Lectures 14 & 15 SUBSTITUTION REACTIONS: S N 1 vs. S N 2 All of the following substitution reactions proceed as shown (there may be some elimination products as well, but we’ll worry about that later). At first glance, the products of substitution reactions are the same whether they go by S N 1 or S
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