Organic and Main Group Chemistry
In the presence of strong acids and water, carbon monoxide reacts with alkenes to form carboxylic acids in a process known as the Koch–Haaf reaction. In the Gattermann-Koch reaction, arenes are converted to benzaldehyde derivatives in the presence of AlCl3 and HCl. Organolithium compounds (e.g. butyl lithium) react with carbon monoxide, but these reactions have little scientific use.
Although CO reacts with carbocations and carbanions, it is relatively nonreactive toward organic compounds without the intervention of metal catalysts.
With main group reagents, CO undergoes several noteworthy reactions. Chlorination of CO is the industrial route to the important compound phosgene. With borane CO forms an adduct, H3BCO, which is isoelectronic with the acylium cation +. CO reacts with sodium to give products resulting from C-C coupling such as sodium acetylenediolate 2Na+·C2O2−
2. It reacts with molten potassium to give a mixture of an organometallic compound, potassium acetylenediolate 2K+·C2O2−
2, potassium benzenehexolate 6K+ C6O6−
6, and potassium rhodizonate 2K+·C6O2−
6.
The compounds cyclohexanehexone or triquinoyl (C6O6) and cyclopentanepentone or leuconic acid (C5O5), which so far have been obtained only in trace amounts, can be regarded as polymers of carbon monoxide.
At pressures of over 5 gigapascals, carbon monoxide disproportionates into carbon dioxide (CO2) and a solid polymer of carbon and oxygen, in 3:2 atomic ratio.
Read more about this topic: Carbon Monoxide
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