Key-Mid-1

Key-Mid-1 - o C j H 3 C H H H 2 C CH 3 N O O Br 1 2 CH 3 S-Na DMF OH OH O O HO OH S Br H H H H S Br H H H H S Br Br S Student Name Problem 3 A

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Student Name:__________________ Problem 1 : Propose a reasonable structure for the compound A on the basis of the given molecular formula and the 1 H NMR and 13 C spectras. Assign the signals to specific hydrogens in the molecule. Solvent O
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Student Name:__________________ Problem 2 How many signals would you expect to see in the 1 H NMR and 13 C NMR spectras for each of the following compounds. NO 2 NO 2 NO 2 NO 2 NO 2 NO 2 NO 2 1 H NMR 13 C NMR 3 4 2 3 3 4 1 2
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Student Name:__________________ Problem 3 Predict the expected major products of the following reactions. Include the stereochemistry when it applies. a) Br N Li + THF b) 1) BH 3 2) H 2 O 2 , OH - c) Br O - Na + CH 3 CH 2 OH, 55 o C d) 1) O 3 2) H 2 O 2 , OH - e) H 2 O, H 2 SO 4 f) H Br H O - Na + CH 3 CH 2 OH, 55
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Unformatted text preview: o C j) H 3 C H H H 2 C CH 3 N O O Br 1) 2) CH 3 S-Na + , DMF OH + OH O O HO OH S Br H H H H S Br H H H H S Br Br S + + Student Name:__________________ Problem 3 A) Provide a synthetic strategy for the following transformation. Show all intermediates and reagents needed for the reaction. (No mechanism) Cl Br OH HBr/ROOR LDA THF 1) B 2 H 6 2) H 2 O 2 , NaOH/H 2 O SOCl 2 /Pyridine DCM B) Complete the following reactions. Pay attention to the stereochemistry when it applies. 1) O 3 2) Zn/CH 3 COOH 1) 2) HCl/H 2 O 3) 4) 1) Br 2 , h υ 2) Mg, ether O 1) 2) H + /H 2 O H 2 /Pd O O Cl MgBr OH (R,S) +...
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This note was uploaded on 12/16/2008 for the course CHEM 140B taught by Professor Nefzi during the Spring '06 term at UCSD.

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Key-Mid-1 - o C j H 3 C H H H 2 C CH 3 N O O Br 1 2 CH 3 S-Na DMF OH OH O O HO OH S Br H H H H S Br H H H H S Br Br S Student Name Problem 3 A

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