Antioxidants are additives largely used in industry for delaying, retarding, or preventing the development of oxidative deterioration. Propyl gallate (E310) is a phenolic antioxidant extensively used in the food, cosmetics, and pharmaceutical industries. A series of lab experiments have been developed to teach students about the importance and…

Thermotropic liquid crystal phases are ordered fluids found, for some molecules, at intermediate temperatures between the crystal and liquid states. Although technologically important, these materials typically receive little attention in the undergraduate curriculum. Here, we describe a laboratory activity for introductory organic chemistry…

Reactive oxygen species such as singlet oxygen have been a major focus of research in medicine. The effect of singlet oxygen on sterols within biological membranes is becoming increasingly more important. Ergosterol, a vitamin D precursor, is one such sterol. The benzoylation of ergosterol and subsequent reaction with singlet oxygen to form an…

Water is the ideal green solvent for organic reactions. However, most organic molecules are insoluble in it. Herein, we report a laboratory module that takes advantage of this property. The Passerini reaction, a three-component coupling involving an isocyanide, aldehyde, and carboxylic acid, typically requires [similar to] 24 h reaction times in…

The laboratory synthesis of N,N-diethyl-3-methylbenzamide (DEET) is an effective way to combine organic chemistry teaching with a student's day-to-day life outside the classroom. Interest in DEET as a mosquito repellent has been heightened because of the rise of the West Nile virus across much of North America (1). To take advantage of the…

Qualitative organic analysis of an unknown compound is an integral part of the university chemistry laboratory curriculum. This type of training is essential as students learn to approach a problem systematically and to interpret the results logically. However, considerable quantities of waste are generated by using conventional methods of…

The guided-inquiry approach is applied to the reactions of sodium borohydride and phenyl magnesium bromide with benzaldehyde, benzophenone, benzoic anhydride, and ethyl benzoate. Each team of four students receives four unknowns. Students identify the unknowns and their reaction products by using the physical state of the unknown, an…

The research presented in chapters 2, 3, and 4 in this dissertation uses a sociocultural and sociohistorical lens, particularly around power, authority of knowledge and identity formation, to investigate the complexity of engaging in, supporting, and evaluating high-quality argumentation within a college biochemistry inquiry-oriented classroom.…

In this laboratory activity for introductory organic chemistry, students carry out the tin(II) bis(2-ethylhexanoate)/benzyl alcohol mediated ring-opening polymerization of lactide to form the biodegradable polymer polylactide (PLA). As the mechanism of the polymerization is analogous to that of a transesterification reaction, the experiment can be…

The conversion of carboxylic acids to ketones is a useful chemical transformation with a long history. Several chemists have claimed that they discovered the conversion of carboxylic acids to ketones yet in fact the reaction is actually known for centuries.

Presented are the procedures and a discussion of the results for an experiment in which students select unknown carboxylic acids, determine their melting points, and investigate their solubility behavior in water and ethanol. A table of selected carboxylic acids is included. (CW)

Discusses the use of the mixture of a carboxylic acid and sodium borohydride as a reagent. The chemical mechanism of the mixture is described using structural formulas. Lists 15 references. (YP)

Surveys the roots of the common names of organic compounds most likely to be encountered by undergraduate organic chemistry students. Includes information for 19 amino acids, 17 aromatic compounds, and 21 carboxylic acids. (WRM)

Monsanto's highly successful synthesis of acetic acid from methanol and carbon monoxide illustrates use of new starting materials to replace pretroleum-derived ethylene. Outlines the fundamental aspects of the acetic acid process and suggests ways of extending the synthesis to higher carboxylic acids. (JN)

Converting carboxylic acids into their anilides, which usually involves preparation of acid chloride or mixed anhydride followed by treatment with aniline, is tedious and/or time-consuming. A quick and easier procedure, using phenyl isothiocyanate, is provided. Reactions involved and a summary table of results are included. (JN)