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Organic Chemistry 2 Midterm - Part 2 of 4
SAMPLE

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18. Aromaticity / Ionization of Aromatics / Problem 2

Copper iodide (CuI) precipitates when 3-iodocycloprop-1-ene is treated with copper tetrafluoroborate (CuBF4). The organic product formed can be obtained as a solid substance that dissolves readily in polar solvents like ethanol but does not dissolve in non-polar solvents like hexane. 3-iodocycloprop-1-ene gets regenerated when this solid substance is dissolved in ethanol containing potassium iodide (KI). Provide the structure of this solid substance and write down equations for its formation and reaction.

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