SCOPE. OF THE REACTION 97It would be a consequence of this mechanism that under certain condi-tions an ester might be isolated as one of the products of the reaction.-Such is found to be the case. Thus, Lachman19has shown that benzylbenzoate can be isolated in the reaction between benzaldehyde andaqueous sodium hydroxide if precautions are taken to avoid'high tem-perature and an excess of alkali.The view tiiat the first step in the reaction proceeds by an initial co-ordination of the base (e.g., OH~) with the aldehyde carbonyl group issupported by the investigations of Lock,16Molt,20Weissberger andHaase,21and Bailar, Barney, and Miller21° on the effect of substituentsupon the rate of the reaction. Electron-attracting groups (e.g., halo-gen, —NOa) increase the rate, and electron-repelling substituents(e.g., —OCH8, —CH3,- and particularly those groups such as —O~ andNR2 which can furnish electrons directly to the carbonyl carbon atom)decrease the rate.
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