Synthesis Set 1 - Edubirdie

University:
California State University, Northridge
Course:
CHEM 334/L | Organic Chemistry II and Lab
Academic year:

2009
Views:

358

Pages:

2
Author:

Jamal Simon

Chemistry 334 Additional Problem Set #2 Answer Key Synthesis Set #1 As mentioned in lecture, there usually are a number of viable solutions to a synthesis problem. Concise syntheses that avoid product mixtures are preferred. Regio- and stereochemistry must be controlled where appropriate. 1. H O H H2 Pd/BaSO4 quinoline m-CPBA H 3C CH 3 H 3C a.) NaNH2 CH 3 H b.) n-BuI H 3C CH 3 CH 3 2. CH 3 H 3C CN OH CH 3 Br Br O CH 3 b.) H3O+ Cl- H 3C PBr3 H 3C a.) CH 3 H 3C CH 3 NaCN H 3C Mg MgBr 3. CH 3O CH 3 HO CH 3 a.) 2 NaH dil. H3O+ HSO4- b.) 2 H3CI H OCH 3 H (racemic) OH (racemic) CH 3 CH 3 m-CPBA Et2CuLi Br O H (racemic) 4. CH 3O CH 3 HO a.) 2 NaH OsO4 NMO CH 3 b.) 2 H3CI CH 3O aq. t-BuoH H HO (racemic) H (racemic) CH 3 (as above) Et2CuLi Br

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