Prior to the development of the petroleum industry, coal was the promary source of organic chemicals. Acetylene can be synthesized from the carbon in coal, but it takes a couple of steps: |
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Calcium carbide is a diacetylide, and a ready source of the acetylide anion synthon. We've seen it used to make long chain alkynes, and reaction with water forms acetylene and Ca(OH)2. |
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In the 1940s, German chemist Walter Reppe discovered a really neat catalytic way to make 1,3,5,7-cyclooctatetraene. This had previously only been prepared via a very laborious 13-step synthesis in the early 1900s. The mechanism is thought to involve cyclization of two acetylenes on a nickel center to form a "metallacyclopentadiene," and that two of these sequentially link ends to first make a C8 chain, and then the carbocycle: (Fun fact: Dr. Gable did his Ph. D. thesis studying the catalyst and found evidence that it's a complex organic framework assembled from the acetylides that supports a number of reduced Ni atoms. See paper in Organometallics. One application was discovered in the 1990s. Another metal-catalyzed process called "olefin metathesis" essentially switches ends of two molecules with double bonds. When this is done with cyclooctatetraene, the rings open up and link together, resulting eventually in a high polymer. This "Ring-Opening Metathesis Polymerization" or "ROMP" results in a long chain of conjugated double bonds. This is conductive, and its discovery was awarded the Nobel Prize in 2000. A paper with a picture of a sample of conductive polyacetylene: https://iopscience.iop.org/article/10.1088/1757-899X/54/1/012019/pdf |