By P. W. G. Smith and A. R. Tatchell (Auth.)
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Additional info for Fundamental Aliphatic Chemistry. Organic Chemistry for General Degree Students
ROH+HX > RX+ H 2 0 The conditions required depend on the hydrogen halide used, the order of reactivity being HI > HBr > HC1. Thus alkyl iodides are prepared by refluxing the alcohol with an excess of constant boiling hydriodic acid. Alkyl bromides are prepared in a similar way using hydrobromic acid with sulphuric acid as a catalyst; a suitable alternative procedure is to heat the alcohol with a mixture of concentrated aqueous sodium bromide and sulphuric acid. NaBr+H 2 S0 4 > HBr+NaHS0 4 ROH+HBr J ?
RX+CH 3 CH 2 0? ethoxide ion > ROCH2CH3+ :X© Replacement of the halogen by a carboxylate ion gives an ester. This can be effected either by heating the alkyl halide with a solution of the potassium salt of a carboxylic acid in an excess of the acid or more readily by warming with the silver salt in alcohol. g. o II Θ RX+CH3CO: acetate ion >CH 3 C0 2 R+:X e alkyl acetate HALOGEN DERIVATIVES OF ALIPHATIC HYDROCARBONS 57 For those alkyl halides which have a marked tendency to form olefins during alkaline hydrolysis, the hydrolysis of the ester (p.
A further important reaction of alkyl halides is their conversion into olefins, which are unsaturated hydrocarbons. This illustrates another class of organic reactions termed the elimination reaction (E), which in this case involves the elimination from the alkyl halide molecule of a halide ion together with a proton attached to the ß-carbon atom, thereby forming a double bond between the a- and ß-carbon atoms as the following example shows. g. the ethoxide Θ ion, CH 3 CH 2 0:) powerful enough to detach the ß-hydrogen atom (p.