POD16Key - (target, as a racemic mixture) from and O O O CH...

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Problem of the Day #16 - Answer Key Deadline : IN CLASS on Th 8/5/2010 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. In each part below, propose a sequence of reactions to synthesize the target compound from the indicated starting material(s). You may use any other organic and/or inorganic reagents necessary to complete your synthesis, but all carbon atoms in the target must be derived from the starting material(s) specified in each part. [Note : You may use other carbon- containing reagents, as long as they do not contribute carbon atoms to the final target molecule.] It is only necessary to give overall transformations in answering this question. It is not necessary to provide complete curved arrow mechanisms for the reactions that you use. Use the back of the page if you need more space for your answers. (a) (8 points) Prepare
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Unformatted text preview: (target, as a racemic mixture) from and O O O CH 3 CH 2 OH as only sources of carbon atoms found in the target (b) (12 points) Prepare (target) from and as only sources of carbon atoms found in the target O CO 2 Br O O O 1) O 3 2) (CH 3 ) 2 S H H O O NaOH, H 2 O (no heat) OH H O (intramolecular aldol) H 2 CrO 4 O OH O CH 3 CH 2 OH H 2 SO 4 (cat.) (Fischer esterification) O Br 2 4 Li Li + 2 LiBr CuCl 2 (CH 3 CH 2 CH 2 ) 2 CuLi + LiCl Br Mg MgBr 1) CO 2 2) H 3 O + OH O SOCl 2 Cl O 1) (CH 3 CH 2 CH 2 ) 2 CuLi 2) H 2 O Please see the next page for an alternative approach that involves a Dieckmann condensation… 2 O O O 1) O 3 2) H 2 O 2 H H O O O H OH O O CH 3 CH 2 OH H 2 SO 4 (cat.) (Fischer esterification) EtO OEt O O 1) NaOEt, EtOH 2) dil. H 3 O + (Dieckmann condensation) 1) O 3 2) (CH 3 ) 2 S H 2 CrO 4 Alternative answer for Part (a) :...
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This note was uploaded on 10/25/2010 for the course CH 310n taught by Professor Iverson during the Summer '08 term at University of Texas.

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POD16Key - (target, as a racemic mixture) from and O O O CH...

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