Week_2.2_PurpleBook_Answers

Week_2.2_PurpleBook_Answers - 39 More Alkene Addition...

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O Br H 3 C Br Br Br Br Br HO CH 3 O Br H 3 C H More Alkene Addition Mechanisms Br Br 1. Provide complete curved-arrow mechanisms for the following transformations. Br 2 ,CH 3 OH Br :Solvent Br Br 2 Br: Week 2 39
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OCH 3 OAc Hg AcO Hg AcO HO CH 3 OCH 3 H Hg AcO OCH 3 2. Predict the product of the following two-step transformation, and show a complete curved-arrow mechanism for the first step only . AcO Even More Alkene Addition Mechanisms (D = deuterium) DB D 2 1. Provide a complete curved-arrow mechanism for the first step only in the following transformation: D 1. Hg(OAc) 2 ,CH 3 OH 2. NaBH 4 BD 2 1. BD 3 2. H 2 O 2 ,OH D :Solvent OH H 2 O 2 (Note that there is no carbocation rearrangement!) (This borane will react with 2moreequ iva lentso fthea lkene but that doesn't change the eventual product. ..) NaBH 4 Week 2 40
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Putting It Together: Alkene Additions 1. Consider the following reaction: Resonance Explanation: Frontier Molecular Orbital Explanation: b) Explain why product A is observed instead of product B . You should provide both a resonance explanation and an explanation in terms of the molecular orbitals involved. A observed B not observed a) Draw a complete curved-arrow mechanism for the formation of the product A . O CH 3 OH , H + O O 3 O O CH 3 O H + O HOCH 3 O O CH 3 H 3 The carbocation which leads to product A is: which is stabilized by the following, more stable resonance structure: The carbocation which leads to B has no such resonance stabilization (only hyperconjugation).
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This note was uploaded on 05/01/2008 for the course CHEM 51 taught by Professor Gribble during the Spring '08 term at Dartmouth.

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Week_2.2_PurpleBook_Answers - 39 More Alkene Addition...

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