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Preparation

Acetylene is the simplest alkyne and stands out from the industrial point of view. Acetylene can be directly produced from coal following two main industrial procedures:

Berthelot synthesis: coal and hydrogen give acetylene in an electric arc (33%)

Marcellin Berthelot (1827-1907): French chemist and politician. He showed that glycerol is a triol and prepared ethanol, formic acid, methane, acetylene and benzene at a time when the vital force theory was still strongly held. He obtained acetylene by subjecting a mixture of coal and hydrogen to the high temperatures of an electric arc. He is considered the father of thermochemistry, because he began the systematic study of the heat absorbed or released in chemical reactions.

Portrait of Marcellin Berthelot
Coal and lime give calcium carbide at 2000 °C, and the carbide releases acetylene with water

Laboratory procedures

Double elimination reactions

Double elimination of HBr from a vicinal dibromide with a base: a vinyl bromide and then the alkyne

Alkynyl anion alkylation

Alkynides, good nucleophiles, undergo nucleophilic substitution with halides, epoxide opening and addition to carbonyls