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Unformatted text preview: Practice Exam 6 (10/6/10) I. Predict the major product(s) for the following reactions and show the stereochemistry if any. Br CH 3 COO room temperature MeOH 25 C Me Cl NaN 3 25 C ( R )-2-chlorobutane N 3 II. In elimination reactions, t-butyl chloride reacts faster than isobutyl chloride. The difference in reactivities is accounted for by the stabilities of the incipient carbocations. Between the carbocation formed from t-butyl chloride is and the one from isobutyl chloride, which one more stable? Explain why. Cl Cl tertiary: more stable primary; less stable A tertiary carbocation is more stable than the primary one because a tertiary carbocation has more hyperconjugation than the primary. The alkyl substituents offer the delocalization of electrons from C-H bonds to the empty p-orbital in the carbocation center. C C H orbital overlap KO t Bu KO t Bu OCOCH 3 Me OMe MeO Me III. Draw the major product with appropriate stereochemistry. In addition, circle the correct stereochemistry, R or S, of each substrate and product.stereochemistry, R or S, of each substrate and product....
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