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practice-7-key - has more hyperconjugation than the primary...

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Practice Exam 7 (10/17/07) - 15 minutes (7 pts) I. Give the systematic name for the following structure. Cl Br ( Z, 2R )-3-bromo-2-chloro-3-hexene (15 pts) 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. Explain why the carbocation formed from t -butyl chloride is more stable than the one from isobutyl chloride. Cl KO t Bu Cl KO t Bu tertiary: more stable primary; less stable A tertiary carbocation is more stable than the primary one because a tertiary carbocation
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Unformatted text preview: 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 (15 pts) III. For the following elimination reaction, predict the major product and explain why the product of your choice is formed selectively among the possible products. NaOEt heat Cl H Cl Me t Bu Me Cl H t Bu available for β-elimination only possible one for anti-periplanarity in elimination...
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