TY - JOUR
T1 - Azeotropic Preparation of a C-Phenyl N-Aryl Imine
T2 - An Introductory Undergraduate Organic Chemistry Laboratory Experiment
AU - Silverberg, Lee J.
AU - Coyle, David J.
AU - Cannon, Kevin C.
AU - Mathers, Robert T.
AU - Richards, Jeffrey A.
AU - Tierney, John
N1 - Publisher Copyright:
© 2016 The American Chemical Society and Division of Chemical Education, Inc.
PY - 2016/5/10
Y1 - 2016/5/10
N2 - 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.
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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U2 - 10.1021/acs.jchemed.6b00056
DO - 10.1021/acs.jchemed.6b00056
M3 - Article
AN - SCOPUS:84969674648
SN - 0021-9584
VL - 93
SP - 941
EP - 944
JO - Journal of Chemical Education
JF - Journal of Chemical Education
IS - 5
ER -