Problem_Set_6_solution - Chem 3580 - Spring 2009 Problem...

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Chem 3580 - Spring 2009 Problem Set 6 Additional Problems 1. There is always more than one approach to making a particular compound. What follows are just examples of the possible ways of making the given compounds. These are based on what we have done so far. As we learn more and more reactions you will be able to do the same synthesis in fewer steps. You may want to explore on your own alternate methods for each. 1(a) Alkyl chloride is used to show that you do not have to restrict yourself to the bromide. Retrosynthesis HO O ClMg Cl HO HO O Cl O + (CH 3 ) 2 CuLi Forward synthesis OH O 1. LiAlH 4 , ether 2. H + , H 2 O OH SOCl 2 Cl MgCl Mg, ether O 2. H + , H 2 O 1. HO Cl O + (CH 3 ) 2 CuLi O 1(b) Retrosynthesis OH H O O OCH 3 + CH 3 MgBr OH MgBr + Br OH O Forward synthesis O H O 2. H 3 O + OH PBr 3 Br MgBr 1. 2. H 3 O + OH H 2 CrO 4 O OH O OCH 3 Mg, ether 1. NaBH 4 2. H 3 O + OH CH 2 N 2 1. CH 3 Mg r
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The second approach uses epoxide ring opening. This shortens the number of steps considerably. This would have been the preferred route if the use of organic reagents containing 4 carbons were allowed. Retrosynthesis
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Problem_Set_6_solution - Chem 3580 - Spring 2009 Problem...

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