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Organic Chemistry Text Book (CHEM 3401 and 3402)

5.1 Isomerism and Stereoisomerism

As chemists studied organic compounds isolated from plants and animals, a new and subtle type of configurational stereoisomerism was discovered. For example, lactic acid ( a C3H6O3 carboxylic acid) was found in sour milk as well as in the blood and muscle fluids of animals. The physical properties of this simple compound were identical, regardless of the source (m.p, 53 ºC & pKa 3.80), but there was evidence that the physiological behavior of the compound from the two sources was not the same. Another natural product, the fragrant C10H14O ketone carvone, was isolated from both spearmint and caraway. Again, all the physical properties of carvone from these two sources seemed to be identical (b.p. 230 ºC), but the odors of the two carvones were different and reflected their source. Other examples of this kind were encountered, and suspicions of a subtle kind of stereoisomerism were confirmed by the different interaction these compounds displayed with plane polarized light. We now know that this configurational stereoisomerism is due to different right and left-handed forms that certain structures may adopt, in much the same way that a screw may have right or left-handed threads but the same overall size and shape. Isomeric pairs of this kind are termed enantiomers (from the Greek enantion meaning opposite).