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Aromatic Chemistry: Synthesize a Compound

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Synthesize the following compound. You may also use any organic compounds containing three or less carbon atoms, benzene, N-bromosuccinimide, triphenylphosphine, meta-chloroperbenzoic acid (MCPBA), methylvinyl ketone, lithium diisopropylamide (LDA), ethyl acetoacetate (acetoacetic ester) and diethyl malonate (malonic ester), as well as any inorganic reagents.

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Aromatic chemistry is a real toughie as there are so many ways of carrying out a given transformation. It's all about the directing ability of different groups attached to the benzene core. As such, I have attached two ways that you might be able to tackle this synthesis. Both use standard reactions which work. I have listed the names where appropriate so you can look them up and see what's going on. I guess the route that you choose will depend on which is most similar to the kind of stuff that you have encountered in your course.

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Hi,

Aromatic chemistry is a real toughie as there are so many ways of carrying out a given transformation. It's all about the directing ...

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