problemset3 - when C is subjected to the same conditions...

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Massachusetts Institute of Technology Organic Chemistry 5.13 October 8, 2003 Prof. Timothy F. Jamison Problem Set #3 Molecular Orbital Theory and Pericyclic Reactions DUE DATE: Thursday, October 16, 2003 at 12 noon 1. Problem 15-30, Wade, p. 676 (15-30, p. 687 in 4 th edition) 2. Problem 15-33, Wade, p. 676 (15-33, p. 688 in 4 th edition) 3. Using retrosynthetic analysis, propose a synthesis of each of the molecules below using a Diels- Alder reaction in each case. Starting with the Diels-Alder reaction you decide to use, write your synthesis in the “forward” direction, showing all steps and reagents necessary. H (d) CH 3 (a) (b) O O H H O (c) HO OH CH 3 HO O OH CH 3 H OH H O HO O O CH 3 4. Base-promoted elimination of 7-bromo-2,4-cycloheptadien-1-one provides cycloheptatrienone as expected, but in the five-membered ring series, only a “dimeric” product is obtained. Explain. O O O Et 3 N 3 N Br Br O O H H E t 5. Compound A
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Unformatted text preview: when C is subjected to the same conditions. Suggest a mechanism for the conversion of A to B , identify the type of reaction involved, and explain why C does not undergo a similar transformation. H H A B 100 °C 100 °C No reaction H H C 6. Name the type of pericyclic reaction involved in each of the following reactions. Classify each according to the Woodward-Hoffmann rules. That is, indicate how many electrons are involved in each case and comment on the stereochemical course of the reaction where relevant. 7. Propose a synthesis of D from 2,6-dimethylphenol, iodomethane, and trans-1-bromo-2-butene. Use any inorganic reagents (e.g. acids, bases, Lewis acids, etc.) necessary, but no other carbon-containing compounds. Write your synthesis in the forward direction, and show arrow-pushing mechanisms for each step. OCH 3 H 3 C CH 3 D H 3 C...
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problemset3 - when C is subjected to the same conditions...

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