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HW07Key - answers(a Prepare using Cl and H O and CH 3 I as...

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Graded Homework Problem #07 – Answer Key Deadline : 3:00 p.m., Monday, 2/25/08 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. 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
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Unformatted text preview: answers. (a) Prepare using Cl and H O and CH 3 I as only sources of carbon atoms (b) Prepare CH 3 using Br and H H O as only sources of carbon atoms Cl H O Mg THF or ether MgCl 1) 2) H 3 O + OH H 2 CrO 4 O CH 3 I 1) PPh 3 2) BuLi H 2 C PPh 3 H 2 C PPh 3 (any strong base can be used in Step 2 of the ylid preparation reaction) (an organolithium compound can be used instead of a Grignard reagent) (any oxidizing agent EXCEPT Tollens' reagent can be used to oxidize the alcohol) 1) 2) H 3 O + (an organolithium compound can be used instead of a Grignard reagent) CH 3 Br H H O Mg THF or ether MgBr OH PCC H O (PCC MUST be used as the oxidzing agent!) H 2 NNH 2 , KOH, Δ OR Zn(Hg), HCl...
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