Azeotropic Preparation of a C-Phenyl N-Aryl Imine

An Introductory Undergraduate Organic Chemistry Laboratory Experiment

Lee Jonathan Silverberg, David J. Coyle, Kevin Charles Cannon, Robert Timothy Mathers, Jeffrey A. Richards, John Tierney

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Imines are important in biological chemistry and as intermediates in organic synthesis. An experiment for introductory undergraduate organic chemistry is presented in which benzaldehyde was condensed with p-methoxyaniline in toluene to give 4-methoxy-N-(phenylmethylene)benzenamine. Water was removed by azeotropic distillation using a Dean-Stark trap. The reaction was readily performed in one 3 h laboratory period, gave a crystalline product, and was easily followed visually by the amount of water collected. It demonstrated important concepts from second-year undergraduate organic chemistry, including equilibrium processes, condensation reactions, and imine formation. The experiment also gave students exposure to important laboratory techniques including azeotropic distillation, use of a water trap, and mixed-solvent recrystallization.

Original languageEnglish (US)
Pages (from-to)941-944
Number of pages4
JournalJournal of Chemical Education
Volume93
Issue number5
DOIs
StatePublished - May 10 2016

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Imines
laboratory experiment
chemistry
Distillation
water
Water
Condensation reactions
Experiments
experiment
Toluene
Students
Crystalline materials
Organic Chemistry
student

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Education

Cite this

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abstract = "Imines are important in biological chemistry and as intermediates in organic synthesis. An experiment for introductory undergraduate organic chemistry is presented in which benzaldehyde was condensed with p-methoxyaniline in toluene to give 4-methoxy-N-(phenylmethylene)benzenamine. Water was removed by azeotropic distillation using a Dean-Stark trap. The reaction was readily performed in one 3 h laboratory period, gave a crystalline product, and was easily followed visually by the amount of water collected. It demonstrated important concepts from second-year undergraduate organic chemistry, including equilibrium processes, condensation reactions, and imine formation. The experiment also gave students exposure to important laboratory techniques including azeotropic distillation, use of a water trap, and mixed-solvent recrystallization.",
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Azeotropic Preparation of a C-Phenyl N-Aryl Imine : An Introductory Undergraduate Organic Chemistry Laboratory Experiment. / Silverberg, Lee Jonathan; Coyle, David J.; Cannon, Kevin Charles; Mathers, Robert Timothy; Richards, Jeffrey A.; Tierney, John.

In: Journal of Chemical Education, Vol. 93, No. 5, 10.05.2016, p. 941-944.

Research output: Contribution to journalArticle

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AU - Silverberg, Lee Jonathan

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AU - Tierney, John

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AB - Imines are important in biological chemistry and as intermediates in organic synthesis. An experiment for introductory undergraduate organic chemistry is presented in which benzaldehyde was condensed with p-methoxyaniline in toluene to give 4-methoxy-N-(phenylmethylene)benzenamine. Water was removed by azeotropic distillation using a Dean-Stark trap. The reaction was readily performed in one 3 h laboratory period, gave a crystalline product, and was easily followed visually by the amount of water collected. It demonstrated important concepts from second-year undergraduate organic chemistry, including equilibrium processes, condensation reactions, and imine formation. The experiment also gave students exposure to important laboratory techniques including azeotropic distillation, use of a water trap, and mixed-solvent recrystallization.

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