Preparation and Identification of Benzoic Acids and Benzamides: An Organic "Unknown" Lab

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...

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Bibliographic Details
Published inJournal of chemical education Vol. 76; no. 6; p. 828
Main Authors Taber, Douglass F, Nelson, Jade D, Northrop, John P
Format Journal Article
LanguageEnglish
Published Division of Chemical Education 01.06.1999
Subjects
Second-Year Undergraduate
Hands-On Learning / Manipulatives
Qualitative Analysis
Organic Chemistry
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Summary: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.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed076p828