Pethidine, the active ingredient in the narcotic analgesic Demerol, was subjected to two successive exhaustive methylations with Hofmann eliminations, and then ozonolysis, with the following results: 

(a) Propose a structure for pethidine based on this information. 

(b) Propose a synthesis of pethidine that begins with ethyl phenylacetate and cis-1,4-dibromo-2- butene

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1. CH,I 2. Ag:0, H.O 3. A 1. CH,I 2. Ag.0, H;O 3. A 1. O,, CH,CI, 2. Zn, H,O Ci5H2, NO, → C16H23NO2 → C14H1602 → 2 CH,O + ОНС C-CO,CH,CH3 -(CH,),N Pethidine СНО