Putting the squeeze on imine synthesis: citrus juice as a reaction medium in the introductory organic laboratory

Nigam, Manisha; Tuttle, Dylan; Morra, Barbora; Dicks, Andrew P.; Rodrı́guez, Julio

doi:10.1080/17518253.2023.2185107

Cited by 3 publications

(2 citation statements)

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“…155 There are several examples to improve chemistry education and to stimulate a systematic thinking approach into the minds of early researchers and students. [164][165][166][167][168][169] We cannot expect future scientists to create sustainable products if they are not taught how to think sustainable. [170][171][172] Students need to be familiar with concepts such as LCAs, green, circular and sustainable chemistry early on.…”

Section: Transforming Research Itselfmentioning

confidence: 99%

The relevance of sustainable laboratory practices

Freese,

Elzinga,

Heinemann

et al. 2024

RSC Sustain.

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Section: Transforming Research Itselfmentioning

confidence: 99%

The relevance of sustainable laboratory practices

Freese,

Elzinga,

Heinemann

et al. 2024

RSC Sustain.

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“…The synthesis of imines gives many examples of “green” considerations. In some cases, water or fruit juice can be used as a solvent, , microwave radiation can be used as an energy source, or silica can be used as a catalyst in these reactions . Heterogeneous catalysts have also been used in solvent free conditions with various desiccants in order to analyze activity and efficiency for the imine condensation .…”

Section: Green Chemistry Considerationsmentioning

confidence: 99%

Utilizing the Imine Condensation in Organic Chemistry Teaching Laboratories to Reinforce Steric Effects, Electronic Effects, and Green Chemistry Principles

Montag

2023

J. Chem. Educ.

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The imine condensation reaction is commonly addressed in second semester organic chemistry classrooms as imines and their derivatives are found in many pharmaceutical scaffolds and biological and catalytic processes. Despite this, imine condensations are still absent from many organic chemistry laboratory curriculums. The work discussed here focuses on comparing the reactivity of the imine condensation with methyl t-butyl ether versus dichloromethane as the solvent as a way to better understand green chemistry along with analyzing steric and electronic effects on reaction. Three primary butyl amines with differing levels of steric hindrance are reacted with a wide variety of substituted aromatic aldehydes that range from electron donating to electron withdrawing. The products are analyzed using 1H NMR spectroscopy, and the percent conversion for each reaction is determined. The results of this work and strategies for implementation of an imine condensation project in second semester organic chemistry laboratory are presented.

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A Citrus Serenade: An Improved Procedure for the Imine Condensation Reaction in Undergraduate Laboratories

Lee,

Kellenberger,

Borton

et al. 2024

J. Chem. Educ.

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The imine condensation reaction is commonly addressed in second semester organic chemistry classrooms. With recent pushes toward green chemistry and developing safer reactions, there is a growing interest in attempting organic reactions in the presence of water or aqueous solvents. The work discussed here provides an important update to a previously reported laboratory experiment that utilizes freshly squeezed fruit juices and water as the reaction solvents to compare the reactivity of the imine condensation with respect to steric, electronic, and pH effects. Five different aromatic benzaldehyde derivatives are reacted with n-butylamine, sec-butylamine, and tert-butylamine in the presence of an aqueous solvent. Students from multiple sections were able to successfully perform the updated reaction and analyze the products with 1 H NMR spectroscopy, calculate the percent conversion for each reaction, and analyze reaction trends. The conversion rates for this imine condensation laboratory experiment greatly exceed those from our previously reported study which utilized organic solvents (J. Chem. Educ. 2023Educ. , 100 (1111. Strategies for implementation of this updated imine condensation project are presented.

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Putting the squeeze on imine synthesis: citrus juice as a reaction medium in the introductory organic laboratory

Cited by 3 publications

References 39 publications

The relevance of sustainable laboratory practices

The relevance of sustainable laboratory practices

Utilizing the Imine Condensation in Organic Chemistry Teaching Laboratories to Reinforce Steric Effects, Electronic Effects, and Green Chemistry Principles

A Citrus Serenade: An Improved Procedure for the Imine Condensation Reaction in Undergraduate Laboratories

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