(1) Derive a method for the preparation of the following product Ethyl Acetoacetate (2) Propose a synthesis for the following compound using Wittig reaction. Also indicate how the Wittig reagent may be prepared. Indicate if there is a possibility of geometric isomerism for the product and when there is, whether you expect to obtain E/Z isomer or both (3) Propose a two reaction sequence to convert each of the following substrates into the indicated products. Identify the substrate, reagent(s) and catalyst if any used for each reaction (Hint : Each problem will include Aldol or Claisen, Diels Alder, Friedel- Craft's, Grignard or Wittig reaction)
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a. The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene? b. The following products were obtained from the oxidative cleavage of a diene. What is the structure of the diene? SOLUTION TO 33 a. Because only one product is obtained, the reactant must be a cyclic alkene. Numbering the product shows that the carbonyl groups are at $\mathrm{C}-1$ and $\mathrm{C}-6,$ so the double bond in the alkene must be between $\mathrm{C}-1$ and $\mathrm{C}-6,$. SOLUTION TO 33 b. The five-carbon product with two carbonyl groups indicates that the diene must contain five carbons flanked by two double bonds. One of the other two products obtained from ozonolysis has one carbon, and the other has three carbons. Therefore, one carbon must be added to one end of the diene, and three carbons must be added to the other end.
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