Synthesis and Characterization of Aldol Condensation Products from Unknown Aldehydes and Ketones

Angelo, Nicholas G.; Henchey, Laura K.; Waxman, Adam; Canary, James W.; Arora, Paramjit S.; Wink, Donald J.

doi:10.1021/ed084p1816

Cited by 15 publications

(8 citation statements)

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“…Aldol condensation reactions typically yield products in a 1:1 molar ratio, whereas in the presence of excess aldehyde, the reaction yields a double-aldol condensation product. This nucleophilic addition reaction occurs in the presence of a base catalyst, where a carbon–carbon bond is formed between compounds containing a carbonyl group. − …”

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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Section: Introductionmentioning

confidence: 99%

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

2021

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“…Multioutcome experiments (MOEs) are laboratory experiments that build upon the traditional single-outcome expository or unknown-based experiment. − Students completing these experiments have a more individualized laboratory experience and gain practical experience with modern analytical techniques. The inclusion of MOEs in the undergraduate laboratory curriculum also affords opportunities to reinforce concepts taught in the lecture course.…”

Section: Introductionmentioning

confidence: 99%

A Multioutcome Experiment for the Williamson Ether Synthesis

et al. 2020

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Williamson ether experiments are commonly performed by students in undergraduate organic chemistry instructional laboratory courses. In this multioutcome experiment, students were provided 4-bromophenol and one of three alkyl halides: 1-bromopentane, 1-bromobutane, or 1-bromo-3-methylbutane. The alkyl halides served as the unknown component of the experiment, and students were given these three as unknown candidates. After isolating the product from the reaction mixture, students analyzed their products using FT-IR and benchtop 1H NMR spectroscopies. The experimental results herein summarize the inclusion of this experiment in the large enrollment second-semester organic chemistry laboratory course over four semesters.

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“…Here, we have chosen to highlight illustrative examples of a number of chemistry subdisciplines via five FRI Research Streams, to show how each teaches the selected introductory chemistry lab skills, emphasizing the unique nature of each stream’s research: making (synthesis), measuring (UV–vis spectroscopy), and characterization. There are several examples in the chemical education literature for teaching modules that introduce the concepts of Beer’s Law, , synthesis, , and characterization. , Traditional and inquiry-based modules are usually taught over a limited period of time, one to a few weeks. The FRI modules introduce concepts in the context of a research project.…”

Section: Introductionmentioning

confidence: 99%

Teaching through Research: Alignment of Core Chemistry Competencies and Skills within a Multidisciplinary Research Framework

et al. 2017

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Innovative models of teaching through research have broken the long-held paradigm that core chemistry competencies must be taught with predictable, scripted experiments. We describe here five fundamentally different, course-based undergraduate research experiences that integrate faculty research projects, accomplish ACS accreditation objectives, provide the benefits of an early research experience to students, and have resulted in publishable findings. The model detailed is the Freshman Research Initiative (FRI) at The University of Texas at Austin. While there are currently 30+ active FRI research groups, or “streams”, we focus this report on five different chemistry streams in these four areas (organic, inorganic, analytical, and biochemistry) to demonstrate how general chemistry laboratory skills are taught in the context of these varied research disciplines. To illustrate the flexibility of the FRI model for teaching first-year chemistry, we show how each stream teaches students three different skills within the context of their research: making (synthesis), measuring (UV-vis spectroscopy), and characterization. As a unifying example, all five chemistry streams describe using UV–vis spectroscopy to characterize new synthetic molecules, complexes, and compounds, followed by extensive quantitative collection, processing, and analysis of experimental data sets. The FRI model allows full integration of training in mandatory and accredited general chemistry skill sets with open-ended research experiences with unexpected outcomes in undergraduate science curricula. In turn, this model enables undergraduates to be productive contributors to new knowledge and scientific discovery at the earliest levels of the undergraduate experience.

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Synthesis and Characterization of Aldol Condensation Products from Unknown Aldehydes and Ketones

Abstract: Scheme I. Reaction equation for the aldol condensation.

Cited by 15 publications

References 4 publications

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

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

A Multioutcome Experiment for the Williamson Ether Synthesis

Teaching through Research: Alignment of Core Chemistry Competencies and Skills within a Multidisciplinary Research Framework

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