Organic reaction mechanism
Wamser, Carl C. Department of Chemistry, Portland State University, Portland, Oregon.
Last reviewed:April 2019
Show previous versions
- Classification of organic reactions
- Potential energy diagrams
- Activation parameters
- Experimental probes of mechanisms
- Substituent effects and Hammett equation
- Isotope effects and isotopic labeling
- Theoretical correlations
- Additional Reading
A complete, step-by-step account of how a reaction of organic compounds takes place. A fully detailed mechanism would correlate the original structure of the reactants with the final structure of the products and would account for changes in structure and energy throughout the progress of the reaction. A complete mechanism would also account for the formation of any intermediates and the rates of interconversions of all of the various species. Because it is not possible to detect directly all of these details of a reaction, evidence for a reaction mechanism is always indirect. Experiments are designed to produce results that provide logical evidence for (but can never unequivocally prove) a mechanism. For most organic reactions, there are mechanisms that are considered to be well established (that is, plausible) based on bodies of experimental evidence. Nevertheless, new data often become available that provide further insight into new details of a mechanism or that occasionally require a complete revision of an accepted mechanism. A common method for illustrating the progress of a reaction is the potential energy diagram, in which the free energy of the system is plotted as a function of the completion of the reaction (see illustration).
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