Douglass F. Taber, Jade D. Nelson, John P. Northrop
The reaction of an unknown substituted benzene derivative (illustrated by toluene) with oxalyl chloride and aluminum chloride gives the acid chloride. Hydrolysis of the acid chloride gives the acid, and reaction of the acid with concentrated aqueous ammonia gives the benzamide. The equivalent weight of the acid can be determined by titration with standardized aqueous sodium hydroxide. Given this information and the melting points of the acid and the benzamide, it is possible to deduce the structure of the initial unknown.
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