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This study is devoted to the consideration of the processes of the emergence and destruction of synonymy in the diachronic aspect between languages of units of two levels -lexical and educational. Moreover, both levels are interconnected and interdependent, since changes in one of them are necessarily on the other. An important role is given to the value of the context in the processes under study. Recognizing the symbolic nature of the language as an exponent of the linguistic picture of the world of its speakers, the authors analyze the reasons for the convergence and divergence of meanings at different time intervals of both the same word and the same root different affix lexemes. The material for the study was the verbs of the lexicosemantic group «Verbs of placing an object anywhere as a result of a certain action», taken in the same context from the lists of the biographies of the Russian saints Boris and Gleb, created at different times and subsequently translated from Old Russian into modern Russian tongue. The main criterion for the selection of linguistic material was the principle of interchangeability of lexemes in the same contexts, since in relation to diachronic synonymy it is fundamental and objectively reflects the linguistic situation of the linguistic period under consideration. In the course of the study, the authors come to the conclusion that the development of synonymous relations between the analyzed verbs «обертеть», «увертеть» and «ввертеть» influenced by the grammatical characteristics of lexemes and their lexical meaning associated with contextual use. And the frequency or singularity of their use is associated not only and not so much with the dictionary meaning, but with the genre of the text in which this or that verb is used.