SN2 MECHANISM - inversion of configuration...

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S N 2 MECHANISM: BIMOLECULAR SUBSTITUTION - 1° (will not work with 2° or 3°) - strong nucleophile - good leaving group - involves displacement of a leaving group (LG) (usually a halide or tosylate), by a nucleophile - works best with methyl and 1° halides because bulky alkyl groups block the backside attack of the nucleophile, but the rxn does not work with 2° halides (although it is usually accompanied by elimination), and will not react at all with 3° halides - example: Because of the backside attack of the nucleophile,
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Unformatted text preview: inversion of configuration occurs.-Solvents: Protic solvents such as water and alcohols stabilize the nucleophile so much that it won’t react. Therefore, a good polar aprotic solvent is required such as ethers and ketones and halogenated hydrocarbons.-Nucleophiles: A good nucleophile is required since it is involved in the rate-determining step.-Leaving groups: A good leaving group is required, such as a halide or a tosylate, since it is involved in the rate-determining step....
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This note was uploaded on 03/21/2008 for the course CHEM 261 taught by Professor Austell during the Spring '08 term at UNC.

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