ProblemSet7

ProblemSet7 - Br Br ? Br Br ? cis-product trans-product 4)...

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CHEM 3570, FALL 2008 Problem Set 7 Diels Alder + SN2 + Synthesis All the stuff you already know!!!!!!! (these are OLD exam questions and yes they are pretty hard) 1) Provide synthetic routes to each of the four products shown. OH O O O O O O O O ? 2) Provide starting materials, reagents, or major organic products for the following reactions. Remember to clearly show any stereochemistry (relative and absolute) or starting materials/products where needed. Diels-Alder MeO OMe Me Et Me CO 2 Et Diels-Alder OMe EtO 2 C +
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3) Provide reagents for the synthesis of both products shown ( trans and cis ). A detailed reaction mechanism for the formation of both products (show all intermediates and arrow pushing clearly).
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Unformatted text preview: Br Br ? Br Br ? cis-product trans-product 4) Rank the following S N 2 reactions according to how fast/good they are (fastest to slowest) Cl OCH 3 Cl OCH 3 Cl OCH 3 MeO-MeO-Cl OCH 3 MeO-MeO-D A B C 5) Provide a CHEM3570 state of the art synthetic route (reagents/conditions) for the following two products. You are expected to show synthetic intermediates but you DO NOT need to provide a mechanism. ? O Cl S O O Cl S O O RO (TsCl) (MsCl) Mesyl Chloride Tosyl Chloride B-H RO-Cl S O O RO S O O ROMs Base: Usually NaH To make an alcohol into a leaving group Hint for problem 1 and future problems RO S O O-Cl...
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Fall '09 term at Cornell.

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ProblemSet7 - Br Br ? Br Br ? cis-product trans-product 4)...

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