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the formation of an optically inactive product (racemate) as a result of a reaction involving an asymmetric atom. Racemization is caused by the appearance of an intermediate compound (or transition state), not itself possessing an asymmetric atom, which has an equal probability of yielding optical antipodes. The antipodes, in turn, form racemic compounds. The racemization of carboxylic acids, for example, involves enolization:
Racemization occurs in reactions leading to the formation of the flat carbonium ion and in reactions that are carried out through free radicals.