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ERIC Number: EJ1101563
Record Type: Journal
Publication Date: 2016-May
Pages: 4
Abstractor: As Provided
ISSN: ISSN-0021-9584
Reaction of Orthoesters with Amine Hydrochlorides: An Introductory Organic Lab Experiment Combining Synthesis, Spectral Analysis, and Mechanistic Discovery
Saba, Shahrokh; Ciaccio, James A.
Journal of Chemical Education, v93 n5 p945-948 May 2016
While orthoesters are often used by chemists as alkylating, acylating, and formylating agents, they are rarely encountered in introductory organic chemistry curricula. We describe a second-semester organic chemistry laboratory experiment in which students acetylate unknown amine hydrochloride salts with trimethyl orthoacetate (TMOA) in the absence of solvent, monitor the progress of the reaction chromatographically, identify the amide product spectroscopically, and propose a mechanism supported by spectral detection of a transient imidate intermediate in an aliquot removed from the reaction mixture. This operationally straightforward experiment combines synthesis with spectral analysis as part of a mechanistic investigation.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: National Science Foundation (NSF)
Authoring Institution: N/A
Grant or Contract Numbers: DUE9650684