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Exploration of factors affecting the relative rate of electrophilic aromatic bromination
Date
March 20, 2022
The experiment of factors affecting the relative rate of electrophilic aromatic bromination is redesigned to allow students
to investigate the relative rate of not only the activated but also the deactivated substrates through experiment and
deduction. The three parts of the experiment each focus on one topic in electrophilic aromatic substitution (EAS): the
relationship between the electron-donating ability of the substituents and their activating ability, the interplay of inductive
effect and resonance effect, and the additive effect of two substituents in EAS, which guide students to draw their own
conclusions step by step and encourage active learning. The experiment is redesigned to make it easy for students to rank the order of activity of both activating and deactivating substituents. More importantly, the redesigned lab encourages students to ask questions and find answers through the three parts of the experiment and allow students to dig deeper into the subject and understand not only how the rates of EAS are affected by the nature of a substituent, but also what leads to those effects.
In summary, this new experiment of exploration of the relative rate of electrophilic aromatic bromination allows students to take a closer look at not only the activated substituted benzenes but also the deactivated compounds by incorporating a series of disubstituted benzenes that display a range of additive activation/deactivation effect.
to investigate the relative rate of not only the activated but also the deactivated substrates through experiment and
deduction. The three parts of the experiment each focus on one topic in electrophilic aromatic substitution (EAS): the
relationship between the electron-donating ability of the substituents and their activating ability, the interplay of inductive
effect and resonance effect, and the additive effect of two substituents in EAS, which guide students to draw their own
conclusions step by step and encourage active learning. The experiment is redesigned to make it easy for students to rank the order of activity of both activating and deactivating substituents. More importantly, the redesigned lab encourages students to ask questions and find answers through the three parts of the experiment and allow students to dig deeper into the subject and understand not only how the rates of EAS are affected by the nature of a substituent, but also what leads to those effects.
In summary, this new experiment of exploration of the relative rate of electrophilic aromatic bromination allows students to take a closer look at not only the activated substituted benzenes but also the deactivated compounds by incorporating a series of disubstituted benzenes that display a range of additive activation/deactivation effect.
Presenter
Caldwell University
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