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Detailed synthesis of aromatic organic compounds

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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Solution Summary

This solution performs two syntheses of compounds.