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CHM 151 (PS 5 F07)

CHM 151 (PS 5 F07) - CHEMISTRY 151L.001 Fall 2006 Problem...

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CHEMISTRY 151L.001 Fall 2006 Problem Set 5 October 16-20 1 Organizing your toolbox: Alkene Reactions a) Write the structure of the major organic product for each of the following reactions. b) Indicate which of the mechanisms involves: i) a carbocation intermediate. ii) concerted addition of A-B to the alkene iii) a 3-membered ring intermediate iv) a catalyst v) rearrangements c) For those reactions marked with an asterix be able to explain the regioslectivity of the reactions with a combination of words and structures. H 2 O cat. H 2 SO 4 1. BH 3 , THF 2. H 2 O 2 , NaOH 1. Hg(OAc) 2 , H 2 O 2. NaBH 4 Br 2 , H 2 O Cl 2 H 2 (g), Pd/C HBr (dark) HBr AIBN, h ! 1.O 3 2. H 2 O 2 , NaOH H 2 O 1.O 3 2. H 2 O 2 , NaOH H 2 O
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CHM 151 (HLS); Problem Set 5 2 2 Introduction to basic synthesis. Suggest structures for the alkenes that would give the following products. More than one possible answer may be acceptable for some questions. a. 1. Hg(OAc) 2 , H 2 O CH 3 CH 2 CH 2 CH(OH)CH 3 2. NaBH 4 b.
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