# An Undergraduate Chemistry Experiment Integrating Theoretical and Practical Aspects of Hypervalent Iodine(I) Compounds

## TL;DR

This paper describes a safe and educational undergraduate chemistry experiment that combines theory and practice in making iodinating agents and applying them in synthesis.

## Contribution

A safe, high-yield method for producing iodinating agents with integrated educational value for undergraduate chemistry students.

## Key findings

- The experiment successfully produces PyICl and PyHICl2 in high yield using safe methods.
- Students gain hands-on experience in synthesis and instrumental analysis through the experiment.
- The method is suitable for both educational and practical benchtop chemistry applications.

## Abstract

A simple reaction sequence has been developed to produce
iodine
chloride-pyridine (PyICl) and pyridinium dichloroiodate (PyHICl2), convenient iodinating agents, in a high yield. Our approach
is safe and simple to handle, avoiding the use of elemental chlorine
or hazardous manipulations. Designed for an upper-level undergraduate
hybrid lecture/lab chemistry course, the experiment integrates key
concepts from both inorganic and organic chemistry. The pre-experiment
lecture explains the connections between molecular structure, reactivity
trends, and reaction types. Over three 4 h lab sessions, students
carry out a sequence of quantitative transformations and characterize
each intermediate and the final product using ESI mass spectrometry,
as well as 1H and 13C NMR spectroscopy. They
also apply the PyICl adduct for electrophilic iodination of salicylic
acid. This experiment reinforces theoretical knowledge while providing
hands-on experience in inorganic and organic synthesis and instrumental
analysis. This material, along with its educational value, can also
be useful to practical benchtop chemists working in the research and
development sector.