Nucleophilic Aromatic Substitution, A Guided Inquiry Laboratory Experiment

Area of Science:

• Organic Chemistry Education
• Chemical Synthesis

Background:

• Inquiry-based learning (IBL) promotes active learning and critical thinking in science education.
• Traditional organic chemistry curricula often focus on electrophilic aromatic substitution, neglecting nucleophilic aromatic substitution (NAS).
• NAS reactions, such as N-arylation of anilines, are valuable for synthesizing important chemical compounds.

Purpose of the Study:

• To develop a straightforward, inquiry-based laboratory experiment for undergraduate organic chemistry.
• To integrate nucleophilic aromatic substitution (specifically N-arylation of aniline derivatives) into the undergraduate curriculum.
• To investigate the reaction rates of NAS using various electrophiles under microwave irradiation.

Main Methods:

• Developed an inquiry-based learning procedure for NAS.
• Utilized microwave irradiation to accelerate the N-arylation of aniline derivatives.
• Designed the experiment to be completed within a single undergraduate laboratory period.

Main Results:

• Successfully implemented a novel NAS experiment within an IBL framework.
• Demonstrated the feasibility of exploring reaction rates of NAS with different electrophiles.
• The experiment was completed efficiently in one laboratory session.

Conclusions:

• The developed inquiry-based experiment effectively introduces nucleophilic aromatic substitution to undergraduate organic chemistry students.
• Microwave-assisted N-arylation provides a practical and time-efficient method for laboratory study.
• This approach enhances student engagement and problem-solving skills in organic synthesis.