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Problem_Set_1_S07 - reactions to work well OH 4 Diels-Alder...

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Chem 358 Spring 2007 Problem Set #1 (Jan 22, 2007) Problems from the Text: 15. 2, 5, 9, 11, 12(b) and (c), 13, 14, 17, 21, 22, 23, 27, 36, 47, 53, 56 Additional Problems 1. Give the structures of all possible products of the acid-catalyzed dehydration of vitamin A. OH H 3 O + Vitamin A (Retinol) 2. Propose a synthesis of each of the following molecules using Diels-Alder reaction. CN CN H O OCH 3 OCH 3 O O (a) (b) (c) 3. Propose an efficient synthesis of the cyclohexenol shown below beginning exclusively with acyclic starting materials and employing sound retrosynthetic analysis strategy. [Hint: A Diels-Alder reaction may be useful but take note of the structural features in dienes and dienophiles that permit Diels Alder
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Unformatted text preview: reactions to work well.] OH 4. Diels-Alder cycloaddition reaction shown below gives a single product. The reaction takes place at only one of the two carbon-carbon double bonds in the cyclic dienophile. Give the structure of the product and explain your answer. Be sure to show the stereochemistry of the product. O O CH 3 O + Single Product [This transformation was the initial step in the total synthesis of cholesterol completed by R. B. Woodward in 1951. This achievement, monumental for its time, revolutionized synthetic organic chemistry.]...
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