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CARBINOLAMINES AND GEMINAL DIOLS IN AQUEOUS ENVIRONMENTAL ORGANIC CHEMISTRY
Citation:
Urbansky*, E T. CARBINOLAMINES AND GEMINAL DIOLS IN AQUEOUS ENVIRONMENTAL ORGANIC CHEMISTRY. JOURNAL OF CHEMICAL EDUCATION 77(12):1644-1647, (2000).
Description:
Organic chemistry textbooks generally treat geminal diols as curiosities-exceptions to the stability of the C=O double bond. However, most aldehydes of environmental significance, to wit, trichloroethanal (chloral), methanala (formaldehyde), ethanal (acetaldehyde), and propanal (propionaldehyde) exhibit this behavior. Carbinolamines (hemiaminals) are usually considered to be unstable reaction intermediates of very short lifetime, despite a considerable volume of literature that suggests otherwise. In aqueous solution, carbinolamines can build up to substantial concentrations and play important roles in kinetics of aldehyde reactions, subsequent to formation of aldehydes as ozonation byproducts during drinking water disinfection. A few carbinolamines are isolable, although these are not encountered in environmental systems. In general, the minimal conceptual treatment of these chemical species results from the central theme of synthetic utility that quite reasonably dominates organic chemistry courses and textbooks. Nonetheless, a pedagogical consequence is that students may be left with an incorrect perception that these species are unlikely to be encountered in common situations. Accordingly, it is important for teachers and students of environmental chemistry to remember that aqueous chemistry can be quite different from that observed in less polar and sometimes aprotic organic solvents.