Problem_Set_3_Answer_Key

Problem_Set_3_Answer_Key - Organic Chemistry c3444y Problem...

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O O KOH, H 2 O Me Me O O HO O Me Me O O H O Δ KOH, H 2 O Organic Chemistry c3444y 1. Propose a synthesis to accomplish the following transformation: (Hint: Work backwards from the product one step. Then try to find similarities in the carbon atom connectivity between that intermediate and the starting material.) ? Problem Set 3 - Answer Key a. 2. Predict the product of the following reactions: b. As we discussed in class, we have here a case of a starting material that, in principle, is an aldol condensation product, but one that violates the first rule. So first simply unravel it to the diketone, as shown, and then simply apply the two rules to figure out where it will end up. Strict application of the two rules for intra- molecular aldol conden- sations will lead to this product (an ethyl group is more hindered than a methyl group). 1. LiAlH 4 2. H 3 O + CrO 3 , Pyridine It's very important to be able to quickly work backwards from an aldol product. In this case, once you do that the relationship between
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Problem_Set_3_Answer_Key - Organic Chemistry c3444y Problem...

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