U-M CHEM 210 - Lecture Notes (5 pages)

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Lecture Notes



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Lecture Notes

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Pages:
5
School:
University of Michigan
Course:
Chem 210 - Struct & React I
Struct & React I Documents

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KEY Name Page 1 I 28 points Complete the f ollowing reactions as directed Transformations requiring sequential experimental steps should be numbered appropriately Show the major organic product s unless otherwise specif ied Abbreviations f or reagents are not allowed If a product f orms as a stereoisomeric mixture draw one and write enantiomer or diastereomer in the box A HO 1 Na NH3 Na Br H2 H 2 OsO4 C C C CH3 OH 1 NaH C H 4 H C C CH3 only this product continues 2 CH3Br 4 H2 CH2CH2CH3 Pd C B 4 H3C H3C C O H3C K Br O O O O H only this alkene p roduct 4 4 C O OH 1 O3 CH2CH3 OH 2 H2O2 OH O CH2CH3 H Ph H Ph 1 NaNH2 CH2CH3 2 PhCH2I O 4 H Ph CH2Ph 4 KEY Name II 24 points Page 2 Compound B undergoes bimolecular elimination when treated with NaOCH2CH3 to f orm a single A major product i Draw the curved arrow mechanism for this reaction using the chair conf ormation that gives the fastest rate of elimination and ii Draw the elimination product Product C i curved arrow mechanism f or reaction with NaOCH2CH3 CH3CH2O CH2CH3 Br H CH3CH2OH C H H3C H HC CH3 H3C H CH2CH3 CH2CH3 H NaOCH2CH3 H Br C H3C H CH3 CH3 Compound B 8 B CH2CH3 ii Major elimination product 4 Product C i Compound D is a stereoisomer of Compound B The rate of bimolecular elimation of Compound D to f orm Product C above is expected to be Br the same as f aster than slower than circle one the rate of bimolecular elimation of Compound B to form Product C H3C C H CH3 Compound D 2 ii In one or two sentences explain why the rate would or would not change as indicated in part i above The isopropyl group would be equitorial on the ring in Compound D f or the conf ormation that allows E2 Since that is a more stable conformation than the conf ormation shown f or Compound B the molecule would spend more time in that conf ormation and E2 would occur more rapidly 4 diastereomers iii Compound B and Compound D are best described as being of each other 2 C The f ollowing results in more than one product Write all predicted



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