exp38[final touch]

exp38[final touch] - To: Meili M Carpenter Section: MC1...

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Section: MC1 From: NAFE QURESHI Date: 3/29/2007 Subject: Experiment #38- Wittig Synthesis of 1,4-Diphenyl-1,3-butadiene Partner: Arthur Hudley Introduction: The purpose of this experiment was synthesize 1,4-Diphenyl-1,3-butadiene from benzyl triphenylphosphonium chloride and pure trans-cinnamaldehyde using Wittig reaction process to convert the carbonyl group in trans-cinnamaldehyde into a carbon carbon double bond. Reaction Mechanism: 1, 4-Diphenyl-1, 3-butadiene can be prepared from cinnamaldehyde by a procedure known as the Wittig synthesis, but its value as Diels-Alder diene will depend on its stereochemistry. The (E,E) diene can easily attain the s-cis conformation needed to form a Diels-Alder adduct, but the (E,Z) diene is less likely to do so. The purpose of the experiment is to find out whether or not one can prepare 1, 4-Diphenyl-1, 3- butadiene from trans-cinnamaldehyde and whether or not the major product has the desired (E,E) stereochemistry. heat + NaOEt + - Ph 3 P: + PhCH 2 Cl -------> (Ph 3 P-CH 2 Ph) Cl - -------> Ph 3 P=CHPh <---> Ph 3 P-CHPh + NaCl triphenyl- benzyl xylenes benzyltriphenyl ylide phosphine chloride phosphonium chloride (Wittig reagent) (Wittig salt)
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This note was uploaded on 11/10/2010 for the course CHE 201 taught by Professor Bong during the Spring '08 term at SUNY Buffalo.

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exp38[final touch] - To: Meili M Carpenter Section: MC1...

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