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Unformatted text preview: from as only sources of carbon atoms H O OH O and Br and CH 3 I (a) (8 points) Prepare (target, as a racemic mixture) from and as only sources of carbon atoms OH O OH Br O CO 2 Br O O H OH H 2 SO 4 (cat.) Br O O Mg MgBr O O 1) CO 2 2) H 3 O + OH O O NaBH 4 in CH 3 OH OH O OH (racemic) The ketone must be protected before preparation of the Grignard reagent. A Gringard reagent would react with an unprotected ketone!!! The acetal protecting group will be hydrolyzed upon the acid workup to yield the deprotected ketone Only the ketone will be reduced if NaBH 4 is used. LiAlH 4 would also reduce the carboxylic acid!!! Mg H O OH O Br CH 3 I MgBr 1) PPh 3 2) BuLi H 2 C PPh 3 2) H 3 O + MgBr 1) OH H 2 CrO 4 O H 2 C PPh 3 1) BH 3 2) H 2 O 2 , NaOH, H 2 O OH H 2 CrO 4...
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This note was uploaded on 09/17/2008 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas.
- Spring '08