Crossed Aldol Reactions in Water Using Inexpensive and Easily Available Materials as a Tool for Reaction Optimization Teaching in an Undergraduate Organic Chemistry Laboratory

Ruiz, Kevin A.; López, M. Allué; Suppan, Gottfried; Makowski, Kamil

doi:10.1021/acs.jchemed.0c00519

Cited by 5 publications

(2 citation statements)

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“…Efforts have been made to introduce greener chemical methodologies for carrying out aldol condensations, including the use of biologically benign catalysts and solvents, and solvent-free reactions that minimize the amount of hazardous organic chemical waste and reduce energy consumption . In an attempt to make a contribution to these endeavors, a multistep synthesis of 4-carbethoxy-2-(4′-hydroxy-3′-methoxybenzylidene)-5-methyl-3(2 H )-furanone ( 4 ) involving an acid-catalyzed aldol condensation is presented (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Multistep Synthesis of a 3(2H)-Furanone Featuring a Green Aldol Condensation

Yousef

Smith

2022

J. Chem. Educ.

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A multistep synthesis of a novel arylidene 3(2H)furanone has been designed and optimized for the second-year organic laboratory. The three-step sequence consists of a nucleophilic substitution, intramolecular cyclization, and acidcatalyzed aldol condensation, and can be carried out within two 3 h laboratory periods. The final product is a crystalline solid that does not require purification and bears structural resemblance to natural products with medicinal properties. Reactions are performed at room temperature, and the aldol condensation takes place without the need for organic solvent, providing students hands-on experience with chemical transformations that illustrate green chemistry principles.

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Section: Introductionmentioning

confidence: 99%

Multistep Synthesis of a 3(2H)-Furanone Featuring a Green Aldol Condensation

Yousef

Smith

2022

J. Chem. Educ.

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“…One aldol experiment employs green chemistry concepts, in which students use cinnamaldehyde isolated from cinnamon to create an aldol product . Another focuses on optimization of the aldol condensation reaction in the undergraduate lab using two relatively accessible reagents, vanillin and cinnamaldehyde from cinnamon bark . The main objective in this project compared to other procedures in the literature, including those mentioned previously, is the in-depth analysis of the aldol products using gas chromatography–mass spectrometry (GC–MS) and the presentation of instrumental details relating to the gas chromatogram–mass spectrometer.…”

Section: Introductionmentioning

confidence: 99%

Gas Chromatography–Mass Spectrometric Analysis of Derivatives of Dibenzalacetone Aldol Products

2021

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The aldol condensation reaction is one of the many synthesis reactions carried out in second semester organic chemistry laboratories. This reaction was integrated into a novel experiment requiring students to synthesize dibenzalacetone derivatives using the crossed-aldol condensation by reacting different types of benzaldehyde derivatives with acetone, followed by analyzing those products using spectrometric and spectroscopic methods, especially gas chromatography−mass spectrometry (GC−MS). The main objective of this 2 week lab experiment compared to other procedures in the literature was the analysis of the final aldol product using GC−MS methods rather than solely nuclear magnetic resonance (NMR) spectroscopic methods. During the first week's 3 h laboratory period, students completed the reaction with a known benzaldehyde derivative and acetone to synthesize their aldol product. In the second week, students calculated the percent yield of their product, determined the product's melting point range, and analyzed the product by thin-layer chromatography, NMR, and GC−MS methods. Students also strengthened their skills of spectral interpretation using NMR spectroscopy, especially distortionless enhancement by polarization transfer NMR, an NMR technique rarely covered in undergraduate organic laboratory sections. Students spent more classroom time during week two, analyzing GC−MS data. Students were shown how to use molecular model kits to understand the fragmentation of compounds in the mass spectrum. As a result, the students who performed this experiment increased their general knowledge of GC−MS spectrometric techniques, including identification of compounds based on their fragmentation pattern.

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Reaction Optimization Experiment for Undergraduate Capstone Organic Chemistry Laboratory Course

Sridhar,

Goloverda

2024

J. Chem. Educ.

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Molecular Structure and Organic Synthesis (MSOS) is an upper-division undergraduate (capstone) laboratory course for undergraduates majoring in chemistry at Xavier University of Louisiana (XULA). The course is designed for juniors and seniors and is based on self-regulated research and learning under limited instructor supervision. It includes a 2-step synthetic project, chosen by each student in the class from a list based on the Organic Synthesis periodical or actual faculty research and then carried out independently. In order to prepare students for their syntheses, we recently included a new project in the course syllabus focused on a reaction optimization that introduces the undergraduate students to the concepts of raising reaction yield, improving product purity, lessening the environmental impact of the reaction, and/or increasing its cost efficiency. A team of 2−3 students performs a preliminary experiment. A rerun by each individual team member incorporating his or her modifications follows this. The goal of this preparatory exercise is to enhance the students' soft skills, including teamwork, critical analysis of data, and scientific report preparation as well as develop a deeper understanding of the reaction mechanism to make calculated adjustments to reaction conditions for optimization.

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Crossed Aldol Reactions in Water Using Inexpensive and Easily Available Materials as a Tool for Reaction Optimization Teaching in an Undergraduate Organic Chemistry Laboratory

Cited by 5 publications

References 20 publications

Multistep Synthesis of a 3(2H)-Furanone Featuring a Green Aldol Condensation

Multistep Synthesis of a 3(2H)-Furanone Featuring a Green Aldol Condensation

Gas Chromatography–Mass Spectrometric Analysis of Derivatives of Dibenzalacetone Aldol Products

Reaction Optimization Experiment for Undergraduate Capstone Organic Chemistry Laboratory Course

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