HW15Key - (a) Prepare from as only sources of carbon atoms...

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Graded Homework Problem #15 – Answer Key Deadline : 3:00 p.m., Monday, 4/7/08 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. Use the back of the page if you need more space for your answers.
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Unformatted text preview: (a) Prepare from as only sources of carbon atoms NH 2 O EtO OEt O O and CH 3 I (b) Prepare from as only sources of carbon atoms (racemic) O H and CH 3 I O (enolate formation followed by alkylation) 2) 1) NaOH, H 2 O H 3 O + , (saponification followed by decarboxylation) EtO OEt O O 1) NaOEt, EtOH 2) CH 3 I EtO OEt O O 1) NaOEt, EtOH 2) CH 3 I EtO OEt O O (enolate formation followed by alkylation) O H O SOCl 2 Cl O NH 3 (2 eq.) N H 2 O 4 Li 2 CH 3 I CuCl + LiCl 1) (CH 3 ) 2 CuLi 2) dil. H 3 O + (conjugate addtion of Gilman) The methyl groups in the Gilman reagent originate in CH 3 I: 2 CH 3 Li (CH 3 ) 2 CuLi + LiI O O (racemic) O H (Grignard addition) 1) CH 3 MgI 2) H 3 O + The Grignard reagent is prepared via rxn of CH 3 I with Mg....
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