' ADDITION TO A DOUBLE BOND 67 Reversing the order of addition, or using an ether as a solvent, causes a marked retardation of the reaction, with subsequent sudden, uncon-trollable speed-up. Yields of about 80% are obtained and probably can be improved by devices to minimize the mechanical losses. 60 The addition of hydrogen fluoride to stearolic acid in methylene chlo-ride solution to give 9,10-difluorostearic acid is cited in the patent litera-ture. 46 This claim should be verified, as either 9,9- or 10,10-difluoro-stearic acid or a mixture is much more likely to be the reaction product. ADDITION TO A DOUBLE BOND Hydrogen fluoride reacts with olefins to yield monofluoroalkanes, 46-47 but very few experimental details have been published. The reaction is reversible and is often accompanied by polymerization of the olefin, which is favored by excess hydrogen fluoride. The difficulties increase if the product is a secondary and especially a tertiary fluoride. Concen-trated aqueous hydrofluoric acid does not react with olefins. The opera-
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.