Chem210-1 F08 Ex3 p04a

Chem210-1 F08 Ex3 p04a - H3C 4. Consider compound 'Z' shown...

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4. Consider compound 'Z' shown on the right: C CH 3 CO 2 O 2 C H 3 C a) Reaction of the dicarboxylate salt 'Z' with bromine water (Br 2 in H 2 O) yielded two major m o n o bromo products, 'D' and 'E'. Compound 'D' has 2 elements of unsaturation; compound 'E' has 3 elements of unsaturation. Propose possible structures for 'D' and 'E' (each has several stereoisomeric forms - you only need show one form for each, as long as it's a stereoisomer that could actually form) AND in each case, provide a step-by-step mechanism for the process in question. Make sure your mechanism includes all significant intermediates which affect the outcome of the reaction.
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