This synthesis of ethyl 6-acetoxyhexanoate (Berryflor) is designed as an experiment for use in a second-year organic chemistry course focusing on the synthesis and reaction of esters. The compound is described as having a raspberry-like odor with jasmine and anise aspects. A two-step procedure for its synthesis beginning with inexpensive…

The Clemmensen reduction is a common example of a reaction demonstrating the deoxygenation of carbonyl groups, which is a topic that has been widely studied in the field of organic chemistry. The use of trimethylchlorosilane, as a substitute for concentrated hydrochloric acid, allows for the reduction of carbonyl groups. The Clemmensen reduction…

Single-outcome experiments are used in the undergraduate instructional laboratory, particularly for large lectures associated with multiple sections of instructional laboratories, due in large part to efficiencies associated with chemical purchases, experiment preparations, and assessments. Despite the practical advantages, single-outcome…

A microwave-promoted synthesis of a carbocyclic curcuminoid has been developed for the undergraduate organic chemistry laboratory curriculum. The experiment features several teaching points: A novel Knoevenagel iminium-mediated condensation forms a highly conjugated, intensely colored natural product. Reaction occurs uniquely at the less acidic…

A multistep experiment for a synthesis laboratory course that incorporates topics in organic synthesis, chemical analysis, and instrumental analysis was developed. Students prepared a tertiaryamine-functionalized polyacrylonitrile fiber (PAN[subscript T]F), and it was subsequently utilized as an immobilized catalyst in a three-component…

Nitrate is a crucial parameter for assessing water quality, owing to its dual function in ecological systems. These functions can be beneficial or detrimental depending on whether nitrate concentrations are low or high, respectively. The ultraviolet spectrophotometric method (standard as 4500-NO[subscript 3]--B) is a classic method for determining…

A one-day laboratory epoxidation experiment, requiring no purification, is described, wherein the students are given an "unknown" stereoisomer of 3-hexen-1-ol, and use [superscript 1]H NMR coupling constants to determine the stereochemistry of their product. From this they work backward to determine the stereochemistry of their starting…

Tetrakis(4-sulfonatophenyl)porphyrin (TSPP) was immobilized on patterned paper and used as a sensor for heavy metal ions in an advanced organic chemistry course. The resulting sensor could detect Hg[superscript 2+] and Cd[superscript 2+] ions colorimetrically, while Cu[superscript 2+] ion resulted in fluorescence quenching, thus demonstrating a…

Students can perceive the laboratory environment in a variety of ways that can affect what they take away from the laboratory course. This qualitative study characterizes undergraduate students' perspectives of a project-based Organic Chemistry laboratory using the theoretical framework of phenomenography. Eighteen participants were interviewed in…

Despite the recognized effectiveness of course-based undergraduate research experiences (CUREs), there are few examples of the development of a CURE-based course in a large-enrollment undergraduate organic chemistry laboratory. Herein, we describe the development and implementation of a series of undergraduate laboratory experiments centered…

The chemistry of metal-organic frameworks (MOFs), a new class of emerging crystalline porous solids with three-dimensional (3D) networks composed of metals and multidentate organic molecules, was introduced by using three differently shaped crystals. We reported new and mild MOF synthesis methods that are simple and devised to be performed in high…

Integrating new synthetic methods and experimental techniques from the latest research reports into undergraduate laboratory experiments is of great significance, as it enables students to learn the cutting-edge technology of organic chemistry and cultivates their experimental skills and innovative thinking. In this study, an experiment on their…

A facile, discovery-based experiment is described that introduces aliphatic substitution in an introductory undergraduate organic chemistry curriculum. Unlike other discovery-based experiments that examine substitution using two competing nucleophiles with a single electrophile, this experiment compares two isomeric, competing electrophiles…

Caffeine (1,3,7-trimethylxanthine) is an alkaloid stimulant that is popular in beverages. Fluorescence-coupled methods have been used to measure the caffeine content in coffee, tea, soft drinks, energy drinks, and cosmetics. In this experiment, we have developed a method for detecting caffeine in beverages utilizing the effect of the caffeine…

While structure-property relationships are commonly developed in applications of physical organic chemistry to real-world problems at the graduate level, they have not been generally emphasized in the undergraduate chemistry curriculum. For instance, the ability to modify the energy gap between the highest occupied molecular orbital (HOMO) and the…