Question

A

co₂Et 4. A Chem 241 student was given an experiment to synthesize compoun OH acetoacetate. The student prepared 1 mole equivalent of methylmagnesium lo which was then slowly added to a solution of ethyl acetoacetate in ether. Every 1 went well, Indeed, even without the annlication of heat the reaction mixture Dubbie orking carefully, with supervision and advice from the lab instructor, the student worked- up the reaction and isolate - LII Caction and isolated an excellent vield of the starting material, ethyl acetoacetate, bu To 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: (0) 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? 4. a) Lily aldehyde (1) is an ingredient used in perfumery. Suggest a synthesis of 1, using as starting materials, the ester 2 and 1-propanol. You may use any other applicable inorganic and/or organic reagents, but LiAlH4, NaOH (aq). PCC, H2, DIBAL, and Pd/C are the most likely choices (depending on your synthetic route). No reaction mechanism(s) is required. Lily aldehyde

Answer 1

4 a) Gnignand reach m On iatone to aet 3al cohst Lo tr I ertuye a ceto aatare Mg IloH) e) Merhane s busbles KMnOu H3THF OH 2) HO/04 ON E+0H OHO H2sOu

pec NaoH 1-Propanat 2 Claisen-Schnidt H ea LALHU 2) Haof CHO Proteetion d etto Liby aldeuyde CHO