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Graded Homework Problem #10 – Answer Key Deadline : 3:00 p.m., Thursday, 3/6/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Each part is worth 10 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. 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.
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Unformatted text preview: Use the back of the page if you need more space for your answers. (a) Prepare from as only sources of carbon atoms OH O O Br O and CO 2 (b) Prepare from as only source of carbon atoms O O OH Br O O H OH cat. H 2 SO 4 Br O O Mg THF MgBr O O 1) CO 2 2) H 3 O + OH O O The ketone must be protected as an acetal before the alkyl bromide can be converted into a Grignard reagent. The acid workup will protonate the carboxylate anion and hydrolyze the acetal to yield the final target compound. OH H 2 Pd (cat.) OH H 2 CrO 4 H 2 O OH O OH cat. H 2 SO 4 O O...
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