Abstract:

The ring-opening reactions of 1,2-epoxides are important topics in organic chemistry courses. The description of the ring-opening reaction of epoxides in textbooks lacks quantitative and visual information; therefore, students usually learn it by rote and cannot fully understand the mechanisms involved. This experiment presents a prototypical example of investigating the molecular mechanism of a chemical reaction using theoretical chemistry methods. By carrying out quantum chemical calculations on the ring-opening reactions of a typical 1,2-epoxide catalyzed by an acid or base, we reveal the thermodynamic and kinetic properties of the reaction and provide an intuitive physical picture and quantitative information of the reaction for understanding the regioselectivity of the reaction. This experiment will not only help students deepen their understanding of the basic concepts and theories of chemistry but also help them broaden their horizons and expand their thinking, making them realize that theoretical calculation is an important tool in chemical research.

Key words: 1, 2-Epoxides, Ring-opening reactions, Methanol, Quantum chemical calculations