Photolytic Degradation as a Means of Organic Structural Determination

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Abstract
The difficulty reported by many authors in obtaining reproducible results in inter-laboratory studies using the pyrolysis-gas chromatographic technique prompted us to investigate other, more reproducible, methods of sample decomposition. The method chosen was mercury-sensitized photolytic decomposition because of the simplicity of the experimental technique, the simplicity of the fragmentation patterns, the predictability of the decomposition products, and the availability of ultraviolet light sources in many well-equipped laboratories. This proved to be a particularly fortunate choice since, not only are results highly reproducible, but preliminary work led to the discovery that functional groups present in a sample may be identified by characteristic constants related to the retention of certain irradiation product peaks called homologous peaks and common peaks, eliminating the need for identification of the decomposition products in evaluating the structure of the sample. In this paper the procedure is discussed in detail and the decomposition product retention parameters are tabulated for aldehydes, ketones, alcohols, esters, and ethers.

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