The thermal equilibration of himic anhydride [IUPAC (2-"endo,"3-"endo")-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride] to (2-"exo,"3-"exo")-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride and subsequent recrystallization of the "exo"-product can be performed as a standard…

A laboratory exercise for the synthesis of a sulfonated styrene-"co"-maleic anhydride polymer and its application as a stain blocker on nylon-6,10, is described. The effectiveness of the sulfonated polymer to prevent the conjugate base of an acid dye from staining the polyamide is demonstrated. This experiment is designed for…

A laboratory experiment is detailed that entails the separation and derivatization of the artificial sweetener sucralose from a commercially available sweetener mixture. The experiment utilizes 1 g packets of a sucralose-based artificial sweetener and involves the separation of the synthetic sweetener from the more polar bulk additives by…

Terms to be familiar with before you start to solve the test: Maxam-Gilbert sequencing, Sanger sequencing, gel electrophoresis, DNA synthesis reaction, polymerase chain reaction, template, primer, DNA polymerase, deoxyribonucleoside triphosphates, orthophosphate, pyrophosphate, nucleoside monophosphates, luminescence, acid anhydride bond,…

A simple, robust, and reproducible method was developed for the isolation of (-)-menthol from peppermint oil and to study the effect of different types of leaving groups, catalysts, solvents, and tertiary base on the extent of esterification of (-)-menthol to (-)-menthyl acetate. In this experiment, students compare leaving group properties of…

A microwave-assisted synthesis of "N"-phenylsuccinimide has been developed for the second-semester organic teaching laboratory. Utilizing this procedure, "N"-phenylsuccinimide can be synthesized in moderate yields (40-60%) by heating a mixture of aniline and succinic anhydride in a domestic microwave oven for four minutes. This technique reduces…

An introduction to the concepts and experimental techniques of diastereoselective synthesis using a chiral auxiliary is described. The 4-benzyl-2-oxazolidinone chiral auxiliary developed by Evans is acylated with propionic anhydride under mild conditions using DMAP as an acyl transfer catalyst. Deprotonation with NaN(TMS)[subscript 2] at -78…

Background information, procedures used, and results obtained are provided for an experiment in which a phase diagram is determined using a differential scanning calorimeter. Commercial samples of D-camphoric anhydride (Eastman Kodak) and D,L-camphoric anhydride (Aldrich) were used in the experiment. (JN)

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…

A reaction kinetics experiment for the chemical engineering undergraduate laboratory course was developed in which in-situ Fourier Transfer Infrared spectroscopy was used to measure reactant and product concentrations. The kinetics of the hydrolysis of acetic anhydride was determined by experiments carried out in a batch reactor. The results…

Describes an undergraduate experiment in which Gantrez AN polymer chains are crosslinked at the anhydride groups by the addition of the hydroxyl groups of triethanolamine, which also acts as a basic catalyst. (MLH)

Describes experiments which can be completed in five four-hour laboratory sessions, including two synthesis (alpha-phenylbutyric and alpha-phenylbutyric acid anhydride) and determining the absolute stereochemistry of secondary alcohols using the synthetic products. (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)

The facile, high yielding synthesis of phenylsuccinamic acids is described and one of these syntheses, the reaction of phenylsuccinic anhydride with tert-butylamine, is successfully modified and adapted for use in the second-semester organic chemistry laboratory at St. John's University. Succinamic acids are compounds that contain both the amide…