Question

OH 4. A Chem 241 student was given an experiment to synthesize compound 1 from ethyl acetoacetate. The student prepared 1 mole equivalent of methylmagnesium iodide, co Et which was then slowly added to a solution of ethyl acetoacetate in ether. Everything went well; indeed, even without the application of heat, the reaction mixture bubbled merrily. Working carefully with supervision and advice from the lab instructor the student worked- up the reaction and isolated an excellent yield of the starting material, ethyl acetoacetate, but not compound 1. The disappointed student reported the result to the lab instructor and asked for a new experiment. (a) What reaction type was the student planning on using to make compound 1? Reaction type (b) What reaction had occurred instead, and write a reaction mechanism to explain what had taken place? (c) What was the cause of the bubbling during the reaction? (d) Can you suggest another way, based on the chemistry we have discussed thus far, for making compound 1 instead of what the student had used above? a) Lily aldehyde (1) is an ingredient used in perfumery. Suggest a synthesis of 1, using as starting materials, the

Answer 1

(a) Nucleophilic addition (Grignard addition to ketone) (6) g Got meange l ost + chyt 8 tot (C) the formation of methane gas (CHy) causes the Guldling ed you have to two substituents in the place of twoh's attached to active methylene group for the desired reaction - H oa twe=98 x 7 Ho, P” RoE