In this two-session experiment for an organic chemistry lab, students prepare a macrocyclic host compound--namely, a pillar[5]arene--by means of a templated 1,4-dimethoxybenzene/formaldehyde cyclo-oligomerization (session 1), and then, they explore its molecular recognition properties toward the 1,8-diaminooctane guest with the aid of [superscript…

Lakes are artists' pigments made from colorants bound to an inert substrate, usually hydrated aluminum oxide. Before the late 19th century, lakes were made from natural pigments extracted from plants and insects, extracted either directly from the dyestuff or indirectly from waste materials generated in the manufacture of dyed textiles. The first…

The dissolution of cobalt­(II) chloride in an appropriate binary alcohol solvent yields an equilibrium mixture, consisting of the differently colored octahedral (pink in color) and tetrahedral (blue in color) cobalt­(II) coordination complexes, which can exhibit a brilliant and reversible pink-to-blue color transition over a ~10 °C window - i.e.,…

In an effort to further develop critical thinking and problem solving skills, a guided-inquiry-based, multioutcome organic chemistry synthesis and characterization experiment was developed. Students were provided with the protocol for a time-saving microwave-assisted acetanilide synthesis reaction from acetic anhydride and an unknown primary aryl…

High-resolution mass spectrometry (HRMS) is an analytical technique that is typically used by mass spectrometry experts. However, with recent advancements, it is becoming more accessible to students in organic chemistry laboratories. Still, a significant knowledge gap exists between these experts and students. A straightforward laboratory…

Benzoin, an [alpha]-hydroxy ketone, is stereoselectively reduced by sodium borohydride to yield hydrobenzoin, the stereochemistry of which is determined by acetalization and analysis of the derivative by NMR spectroscopy. This classical experiment has been enhanced by modern spectroscopic and computational analysis to enable students to…

The particle-in-a-box experiment is a well-known method used to teach quantum mechanics concepts in physical chemistry laboratories for undergraduates. The investigation involves measuring the wavelength at maximum absorbance ([lambda subscript max]) of electronic transitions in the UV-vis spectrum and linking it to the box length. As the…

The carbonyl group of an aldehyde or ketone reacts with different types of nucleophiles through a nucleophilic addition reaction. When the nucleophile is water, the product obtained is a "gem"-diol or geminal diol. This functionalization is unstable and quickly reverts to the parent carbonyl group. The chemistry of "gem"-diols…

Molecular imprinting technology holds significant potential for applications in chemical analysis and detection. In order to integrate the fundamental knowledge of polymer chemistry, electrochemistry, and analytical chemistry with practical applications and cutting-edge research, we proposed a comprehensive experiment of the preparation,…

An integrated laboratory experience using metal--organic frameworks (MOFs), a nanoporous and crystalline extended solid material composed of metal cations and organic linkers, was developed and adopted for upper-division, major-level chemistry and biochemistry students. In this laboratory, students were guided through the facile solvothermal…

This undergraduate laboratory experiment is designed for first-year general chemistry students with the goal of introducing the brilliant colors and magnetic properties of transition metal complexes within a bioinorganic/cell biology context. In the first laboratory period, a coordination complex formed from ferric chloride and maltol is…

A straightforward procedure for the synthesis of (Ph[subscript 3]P)[subscript 3]CuCF[subscript 3], a robust, air-stable trifluoromethylating agent, is reported herein. This preparation can be completed in a single 3 h laboratory session and typically provides ample yields (~79--86%) and high purity (>90%). The target complex is characterized by…

The aroma volatile compounds in tomatoes are strongly linked to taste and flavor. Commercial tomato varieties, however, generally lack flavor. Tomato breeding programs have therefore started to focus on increasing the flavor-enhancing volatiles, which can be more easily altered than the sugar content. Analytical efforts that identify key flavor…

The ability of students to perform quantitative analysis is a fundamental aspect of analytical chemistry courses and laboratories. In this laboratory experiment, students quantitatively analyze both liquid and solid samples through the use of internal standard calibration and ATR-FTIR spectroscopy. Using a problem-based approach to selecting their…

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…