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    Detailed synthesis of aromatic organic compounds

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    I have to perform two synthesises of the compounds shown in the attatchment. I have to use the following starting materials as sources of carbon: benzene, acetylene, diidomethane, carbon dioxide, sodium cyanide, and any monofunctional alcohol with three carbons or less. What are some good suggestions as to the methods/routes I should use to minimize the number of steps?

    (see diagram in attached file)

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    https://brainmass.com/chemistry/organic-reactions/detailed-synthesis-of-aromatic-organic-compounds-58502

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    This solution performs two syntheses of compounds.

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