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Recognize the various nucleophiles and leaving groups and understand the factors that control their reactivities. (Problems 8.9, 8.11, 8.31, 8.32, 8.33, 8.41, 8.42, and 8.52) Understand the factors that control the rates of these reactions, such as steric effects, carbocation stabilities, the nucleophile, the leaving group, and solvent effects. (Problems 8.2, 8.3, 8.6, 8.7, 8.15, 8.22, 8.23, 8.24, 8.25, 8.34, 8.39, 8.55, 8.59, and 8.60) Be able to use these factors to predict whether a particular reaction will proceed by an SN1 or an SN2 mechanism and to predict what effect a change in reaction conditions will have on the reaction rate. (Problems 8.9, 8.11, 8.16, 8.28, 8.36, 8.37, and 8.38) Show the products of any substitution reaction. (Problems 8.12, 8.17, 8.18, 8.26, 8.27, 8.30, 8.40, 8.50, 8.51, and 8.56) Show the stereochemistry of the products. (Problems 8.1, 8.8, 8.27, 8.56, 8.57, and 8.58) Recognize when a carbocation rearrangement is likely to occur and show the products expected from the rearrangement. (Problems 8.19, 8.20, and 8.47.) Show the structures of the products that result from the elimination reactions that compete with the substitution reactions. (Problems 8.18 and 8.46) 130