When FT-NMR is used to collect data without a sufficient delay time between subsequent pulses, the integrated area under certain peaks may result in a lower value than should be observed under appropriate conditions. This discrepancy in integration may deceive the inexperienced eye and consequently can lead to a wrong assignment of the NMR…

Waste newspaper is pulped with acid and its cellulose is hydrolyzed. The resulting glucose syrup is fermented with yeast and distilled to give ethanol. The experiment highlights the potential of applied chemistry to confront problems of economic importance, that is, the effective utilization of biomass to reduce dependence on non-renewable…

Treatment of phenylacetic acid with 90% HNO[subscript 3] yields a product, I, whose observed melting point is 175-179 degrees C and whose equivalent weight is approximately 226 grams. Treatment of phenylacetic acid with 70% HNO[subscript 3] yields a product, II, whose observed melting point is 106-111 degrees C and whose equivalent weight is…

The iodochlorination of styrene, involving the addition of iodine monochloride to styrene, followed by the sodium methoxide-initiated dehydrohalogenation of the product results in a variable mixture of substituted styrenes by way of various substitution and elimination reaction mechanisms. As a result individual results are obtained for each…

This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity in an undergraduate organic chemistry laboratory. Chiral hindered ketones such as estrone, undergo facile reduction with sodium borohydride in a highly diastereoselective manner. The diastereomeric estradiols produced in the reaction can be analyzed and…

Lewis structures are important for learning chemistry as they serve as an essential link between the structure of chemical compounds and their function. Unfortunately, the creation of valid Lewis structures remains an elusive goal for many students. In recent years, several web-based programs have been created that allow students to receive…

The triterpenes are a diverse class of widely distributed natural products derived from squalene. Various cyclization and subsequent rearrangement reactions produce many complex structural types. These compounds frequently display a wide divergence of biological properties. For example the pentacyclic triterpene, betulin, is isolated from white…

A modified Hendrickson, Cram and Hammond (HCH) curriculum was recently introduced in the study of organic chemistry. The approach focuses on the fundamentals and is found to have a lot of positive impact on the students.

We developed and implemented a yearlong safety program into our organic chemistry lab courses that aims to enhance student attitudes toward safety and to ensure students learn to recognize, demonstrate, and assess safe laboratory practices. This active, collaborative program involves the use of student "safety teams" and includes…

Organic chemistry students typically struggle with the retrosynthetic approach to solving synthesis problems because most textbooks present the chemistry grouped by "reactions of the functional group". In contrast, the retrosynthetic approach requires the student to envision "reactions that yield the functional group". A second challenge is the…

This paper describes two techniques for rendering visual concepts encountered in an organic chemistry course into tactile representations for students who have low vision. The techniques--which utilize commercially available products--facilitate communication of organic chemistry between student and instructor. (Contains 1 figure, 2 tables and 1…

The aryl sulfonate ester, menthyl N-acetylsulfanilate, is synthesized from N-acetylsulfanilyl chloride and menthol in pyridine, then pyrolyzed (thermally decomposed) at reduced pressure. The volatile (elimination) products of the reaction are analyzed using gas chromatography, and the resulting product distribution is used to determine whether the…

The use of chiral reagents for the derivatization of optically-active amines and alcohols for the purpose of determining their enantiomeric purity or absolute configuration is a tool used by many chemists. Among the techniques used, Mosher's amide and Mosher's ester analyses are among the most reliable and one of the most often used. Despite this,…

A method for carrying out the Baeyer-Villiger oxidation of cyclopentanone to [delta]-valerolactone in a large-section introductory organic chemistry laboratory course is reported. The oxidizing agent is trifluoroperoxyacetic acid generated in situ from trifluoroacetic acid and household sodium percarbonate such as OxiClean, Oxi Magic, or…

The Robinson annulation is a topic of importance in the second-year organic curriculum. A one-pot, enantioselective Robinson annulation is described. The experiment is completed in two lab periods and is geared towards the second-year organic chemistry major. To our knowledge, this is the first example of a one-pot enantioselective Robinson…