Summary of S N 1/S N 2 and E1/E2 Chemistry S N 2 Reactions: 1. Rate depends upon concentration of the alkyl halide and the concentration of the nucleophile. 2. As the carbon bearing the halide becomes more substituted, the rate of reaction decreases. 3. The rate of reaction also decreases as the size of a substituent on the carbon bearing the halide increases. 4. Substitution of a halide attached to a chirality center leads to the formation of only one stereoisomer in which the configuration of the product is inverted relative to the starting configuration of the alkyl halide. 5. The S N 2 reaction is a one-step bimolecular process with one transition state. • Leaving group ability increases with decreasing basicity. • Nucleophilicity increases with increasing basicity in polar aprotic solvents. • Nucleophilicity typically increases with increasing atomic size in polar protic solvents. •
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