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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 14 Issue 1 (2009) pp 4-9
DOI 10.1333/s00897092181a

Characterization of New and Some Known Organic Compounds: Phenyl Carbazate and its Transformation into HydrazonesA Frugal, Accurate Dean-Stark Trap for the Williamson Microscale Kit

John D. Knight, Derrik L. Weddle II, Julianne McLaughlin, Andrei Straumanis, and Charles F. Beam*

Department of Chemistry and Biochemistry, College of Charleston, Charleston, SC 29424, beamc@cofc.edu
Received July 20, 2007. Accepted January 11, 2008.

Published online: 20 January 2009

Abstract. An advanced organic chemistry laboratory class averaging six-to-seven students per section up to two sections per week during a semester conducted a two-step synthesis by elaboration of the experimental procedures described in two journal articles. Phenyl hydrazinecarboxylate (phenyl carbazate) was prepared by the monohydrazinolysis of phenyl carbonate with hydrazine. This substituted hydrazine was then used to prepare N-carbophenoxyhydrazone derivatives (POC-hydrazone) of aldehydes and ketones. Each student was assigned a different carbonyl-containing compound, and most of the POC-hydrazones prepared were new. Each product prepared was completely characterized by the students. Both preparations employed a minor modification of documented procedures and resulted in improved yields of the targeted products.

Key Words: Laboratories and Demonstrations; organic chemistry; hydrazines; hydrazones; aldehydes; ketones

(*) Corresponding author. (E-mail: beamc@cofc.edu)

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Issue date: February 21, 2009

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