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QUESTION===== Wittig reaction of trans-Cinnamaldehyde using -----preparation of Benzyltriphenyphosphonium chloride and preparation of 1,4- Diphenyl-
QUESTION===== Wittig reaction of trans-Cinnamaldehyde using -----preparation of Benzyltriphenyphosphonium chloride and preparation of 1,4- Diphenyl- 1,3- butadiene(1)Discuss the utility of the Wittig reaction. Look online or in a journal to find an example of the Wittig reaction, or the related Horner-Emmons reaction used in synthesis.(2) Use molecular models or drawings to look at the oxaphosphetane intermediate.(3) What structure would favor a z isomer or the E isomer. (4)Based on this and the stability of the products, which do you think would be the major product in this reaction?(5)Show the mechanism of the subsequent Diels Alder reaction, and predict the stereochemistry of the product of that reaction.(6)Calculate the theoretical yield and the percent yield from the quantities of starting materials and purified product, for both of the reactions. (7)state the melting point range of each of the products. (8)Show the NMR spectra, and correlate, as much as possible, which hydrogens and carbons belong to which Peaks. You may not be able to match everything exactly, but use your knowledge of NMR spectroscopy, and your deductive powers to do as much as you can. (9)From the melting point range and NMR data discuss whether or not a crystallized product was the E,E isomer. A quantity of 3 g of non crystalline product was recovered by washing the ethanol/water filtrates of both of the syntheses with hexanes Assuming the 1.5g came from each reaction mixture, and that it is mostely the ez isomer, estimate aproximatly what percent of the product was ee isomer.(10) Explain whether this matches your prediction in the introduction. (11)Based on the melting point and NMR data you may use, show the structure of the product of the Diels Alder reaction, and describe how you arrived at that structure.(12) Discuss whether or not it matches the structure that you predicted in the introduction.
