Key-Mid-II-Winter%202006

Key-Mid-II-Winter%202006 - step(10 points OH 1 BH 3-THF 2 H...

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Student Name:__________________ Problem 1 : Propose synthetic strategies for the following reactions. Provide all reagents needed and show all the intermediates. (12 points each) A) B) O Br 2 /CCl 4 Br Br NaNH 2 /NH 3 C C (at least 3 equivalents) Li + Br C C H 2 O, H 2 SO 4 , HgSO 4 DMSO HBr CH 3 Hydrogen shift Br- Br- EtO - Na + /EtOH H 2 O/H + CH 3 CH 3 H 2 O H 2 O CH 3 CH 3 OH CH 3 Br H 2 SO 4 , heat Reduction Reduction
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Student Name:__________________ Problem 2 Complete the following reactions. Pay attention to the stereochemistry in (f ) and (g). (32 points, 4 each) Br Mg Eher, 0 o C O 1) 2) H + /H 2 O 1) Hg(OAc) 2 , H 2 O 2) NaBH 4 , NaOH, H 2 O CH 2 N 2 (heat) a) b) c) Br 2 , CCl 4 d) 1) O 3 2) CH 3 SCH 3 e) f) **** g) KMnO 4 OH - /H 2 O 1) BH 3 -THF 2) H 2 O 2 , OH - /H 2 O **** BrMg HO OH Br Br H O O H OH OH + OH OH major minor OH OH +
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Student Name:__________________ Problem 3 a) Provide a synthetic strategy for the following reaction. Show all reagents and intermediates for every
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Unformatted text preview: step. (10 points) OH ??? 1) BH 3-THF 2) H 2 O 2 , OH-/H 2 O OH Na 2 Cr 2 O 7 DMSO O 1)CH 3 MgBr/THF 2)H 2 O/H + b) Provide structural formulas for the reagents or products indicated by letters (20 points, 4 each) CH A B H 2 /Pd/CaCO 3 quinoline C HO 1) Na + NH-2 2) CH 3-I in DMSO D E NaNH 2 /NH 3 A= C Li + B= C= O O D= E= O Student Name:__________________ Problem 4 Complete the following reactions (18 points, 3 each) a) HBr b) 1) O 3 2) (CH 3 ) 2 S c) HBr ROOR d) BH 2 1) 2) H 2 O 2 , OH-/H 2 O e) H 2 /Pd Br 2 , h υ Br + Br H H O O Br Cis/trans H O Br...
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This note was uploaded on 05/03/2009 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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Key-Mid-II-Winter%202006 - step(10 points OH 1 BH 3-THF 2 H...

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