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Solutions to Problems 263 CH₃ CH₃ + 0 Hg(OCCH₃) Hg(OCCH₃)₂ Internal reaction THF (CH₃)₂COH CH₃ CH₃ CH₃ Hg(OCCH₃) O CH₃ O CH₃ NaBH₄ Eucalyptol CH₃ CH₃OH (redrawn) By the way, eucalyptol is just another name for cineole (Chapter 2, Problem 45). 70. Situation similar to that in problem 44(d). CH₃ (a) BH₃ prefers less substituted double bonds because of their reduced steric crowding. CH₃ CH₂OH CH₃ (b) Electrophiles such as MCPBA prefer more substituted double bonds because they are more nucleophilic (electron-rich), and their alkyl groups help stabilize both carbocations and carbocation-resembling transition states. CH₃ CH₂ 71. A "roadmap" problem. Organize your given information and work from it, stepwise, toward the answers. 1. (CH₃CH₂)₂O CH₃ CH₃ 2. CH₃ OH CH₃ CH₂Br CH₃ I 1. BH₃, THF 0 CH₃ 2. PCC, CH₂Cl₂ 3. PCC, CH₂Cl₂ CH₃ CH₂CH₂CCH₃ H J