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problem set 7 key - orgo

problem set 7 key - orgo - OH-1 NaNH 2 2 CH 3 Br H 2 Pd/C...

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Monday Night Problem Set 7 Chemistry 221 Multistep synthesis problems -- show how you would complete the following syntheses. More than one step is necessary in all cases. TIPS Work backwards from product to starting material (retrosynthetic analysis). Most multistep problems at this point will go through an alkyne at some point. Check the # of carbon atoms in the starting material and product. Do you need to add or subtract carbon atoms? Always pay close attention to regio and stereochemistry. Br Br OH - Br 2 dehydrohalogenation Li/NH 3 H 3 C CH 3 H H H 3 C CH 3 H H Br Br Br 2 OH - H 2 Lindlar's catalyst CH 2 I 2 , Zn(Cu) Br 2 Br
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Unformatted text preview: OH-1) NaNH 2 2) CH 3 Br H 2 , Pd/C Show an arrow pushing mechanism for the conversion of the following enol to its keto form. O H O Show the reagents you would use to complete each of the following reactions: H O O HgSO 4 , H 2 O, H + 1) BH 3 THF 2) H 2 O 2 , OH-Write your own multistep synthesis problem using any of the reactions we’ve learned so far. The synthesis should be at least three steps long. Provide the solution to the problem as well. (This is a good way to practice your reactions!) Obviously, there are lots of possible answers here....
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