W08 final

W08 final - ORGANIC CHEMISTRY 30B (Prof. Yves Rubin) UCLA,...

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ORGANIC CHEMISTRY 30B (Prof. Yves Rubin) UCLA, WINTER 2008 FINAL EXAM On my honor, I have neither given nor received any aid on this exam ( Please, use ink for this first page ): ____________________________ __________________________ Signature I. D. Number ____________________________ Full Name ( Please Print ! ) Question Points 1 (20) 2 (30) 3 (30) 4 (20) 5 (25) 6 (25) 7 (20) 8 (30) Total (200) =========
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Organic Chemistry 30B Winter 2008 FINAL EXAM, Page 1 __________________ Name 1. (20 points) a) (6 points) Give the number of expected signals ( ignore splittings) in the 1 H and 13 C NMR spectra of the following compounds: N N O P 1 H NMR: ___________ ___________ ___________ 13 C NMR: ___________ ___________ ___________ b) (8 points) Illustrate the following absorption patterns in a proton NMR spectrum: Sextet Doublet of triplets c) (6 points) Illustrate the following with an example: Diazomethane Cuprate Amides are difficult to hydrolyze, even in aqueous acid. Show why with a brief illustration
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Organic Chemistry 30B Winter 2008 FINAL EXAM, Page 2 __________________ Name 2. (30 points) Draw the major product as well as intermediates for each step (for max. credit) for the following reactions (if there are enantiomers or diastereomers formed, show only one, but pay attention to stereochemistry where needed!) Aqueous workup (e.g. H 3 O + ) is implied after each step where needed: a) 1) PhMgBr 2) PCC 3) CH 2 =CH-Li 4) SOCl 2 5) KCN, DMF
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W08 final - ORGANIC CHEMISTRY 30B (Prof. Yves Rubin) UCLA,...

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