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Organic Lab Reactions 102

Organic Lab Reactions 102 - SCOPE OF THE REACTION 97 It...

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SCOPE. OF THE REACTION 97 It 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, Lachman 19 has shown that benzyl benzoate can be isolated in the reaction between benzaldehyde and aqueous 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 is supported by the investigations of Lock, 16 Molt, 20 Weissberger and Haase, 21 and Bailar, Barney, and Miller 21 ° on the effect of substituents upon the rate of the reaction. Electron-attracting groups (e.g., halo- gen, —NOa) increase the rate, and electron-repelling substituents (e.g., —OCH 8 , —CH 3 ,- and particularly those groups such as —O~ and NR2 which can furnish electrons directly to the carbonyl carbon atom) decrease the rate.
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