Answer Happy

(E)-9-Oxo-2-decenoic acid (compound 2), a pheromone of the honeybee queen, has been shown to have anti-bacterial and antiinflammatory properties. One laboratory synthesis of this pheromone involved the preparation of 1 , followed by the conversion of 1 into 2. (Chem. Nat. Comp. 2011, 47, 789-791) Using an acetoacetic ester synthesis, show how 1 can be converted into 2. Note that the COOH group is mildly acidic, so the investigators first treated 1 with a base (CH3​NH2​) to remove the acidic proton. Make sure to include this deprotonation step in your proposed synthesis. 1 2 The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessy reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A. CH3​NH2​ B. C. D. H3​O+, heat E. NaOEt F. PBr3​