04Exam3-ans

04Exam3-ans - CHEMISTRY 35 Spring 2004 Third EXAM SIS # _...

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CHEMISTRY 35 – Spring 2004 – Third EXAM SIS # __________________ NAME __________________ Problem 1 . (12 points). Provide a detailed, step-by-step mechanism for the following reaction. (Note: we provide the conditions and all the reactants .) (1) show the individual chemical steps and all intermediates formed in the process of converting the reactant into the indicated product. (2) use curved arrows to show all changes in (a) bonding and (b) lone pair electrons (3) show all formal charges and all resonance structures Remember, the sequence of steps you propose must convert the reactant into the indicated product using only the reagents we provide. OSO 3 H HOSO 3 H H OSO 3 H H H OSO 3 H 3 H O H H H H H 2 SO 4 OH heat + ALTERNATIVE Hydride Shift: indicated by red arrow only: bisulfate not involved) 1 point each arrow, 1 pt each formal charge on the organic substrate. Properly indicated Hydride shift is worth 4 points (the same number of points as the deprotonation / reprotonation mechanism)
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CHEMISTRY 35 – Spring 2004 – Third EXAM SIS # __________________ NAME __________________ Problem 2 . (18 points) Provide the structure of the missing component (starting material, reagent(s) or product(s)). Br 2 H 2 O Br HO 2 pt wrong stereoisomer 1 pt O O O O O O Diels Alder 2 pts H 2 O, HgSO 4 , H 2 SO 4 O 2 pts Br Br NaOMe (excess) DMSO OMe + OMe 2 pts Sn2 at 1 o bromide
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04Exam3-ans - CHEMISTRY 35 Spring 2004 Third EXAM SIS # _...

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