The experiment describes the nitration of aromatic compounds and it is designed to highlight three aspects of the chemistry of aromatic compounds:i.   to illustrate a simple organic synthesis involving aromatic nitration;ii. to determine the relative amounts of ortho, meta, and para-nitrotoluenes obtained when toluene is nitrated;iii.   to calculate the relative reactivities of benzene and toluene to nitration.The mixture of benzene and toluene will be reacted with the nitration reagents in the same reaction mixture ensuring that the reaction conditions for the nitration of both aromatic compounds will be the same (temperature, acids concentration, time, etc.).  Quantitative analysis of the product mixture provides both the percent product distribution of the ortho, meta, and para-nitrotoluenes and the total amount of nitrotoluenes and nitrobenzene formed during the reaction, from which the relative reactivities of toluene versus benzene toward nitration is determined.

Competitive nitration of aromatic compounds

248th National Meeting (2014)

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