Hydroboration hydrocarbons, acidity

In the first of these reactions (Equation 11-2), a hydrocarbon is produced by the cleavage of a borane, R3B, with aqueous acid, or better, with anhydrous propanoic acid, CH3CH2C02H. The overall sequence of hydroboration-acid hydrolysis achieves the reduction of a carbon-carbon multiple bond without using hydrogen and a metal catalyst or diimide (Table 11-3) ... 

The saturate and aromatic hydrocarbons were separated from the alcohols by elution chromatography on alumina deactivated with 3.8% water in a ratio of 5 g of alumina to 1 g of oil, by successive elutions with (1) 30 mL of cyclohexane and (2) 50 mL of 2% benzene in cyclohexane. The alcohols were recovered for future analysis by washing the column with 100 mL of ethyl ether. The solvent was removed from the hydrocarbon fraction and the yield of saturates plus aromatics calculated back to the neutral oil. The percentage of olefins was determined by difference. The percentage of aromatic material was determined as the difference between the saturates and aromatics from the hydroboration and the saturates from acid absorption. 

Hunsdiecker reaction, 341 Hybridization, 17 Hybrid orbital number, 17, 18, 32 Hybrid, resonance, 24 Hydration of cyclohexane derivatives, 191 Hydrazine, 4 Hydride shift, 93 Hydroboration, 95 Hydroboration-oxidation, 258, 270 Hydrocarbons, cyclic, 162 unsaturated, 87 Hydrogenation of alkenes, 57 Hydrogen bond, 22 Hydroperoxides in ethers, 284 Hydroquinone, 430 Hydroxy acids, 344... 

Although clearly of use in the synthesis of certain alkylboron compounds, particularly tri-n-alkylboranes and alkylboron hydrides, the hydroboration reaction (developed mainly by H. C. Brown) is of considerable significance in synthetic organic chemistry, as the resulting organoboron compound can be used (without being isolated) as an intermediate in the conversion of olefins or acetylenes into other hydrocarbons (parafi or olefins), alcohols, aldehydes, ketones, carboxylic acids or amines. 

Olefins can also be hydroborated to organoboranes which are then converted to the hydrocarbon by refluxing with propionic acid [1]. This procedure is a convenient noncatalytic laboratory method for the hydrogenation of olefins. 

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