A Case Study Using DFT Calculation Aided Experimental Teaching of Organic Chemistry: Take the Ethyl Acetate Synthesis Experiment as an Example

利用密度泛函理论计算辅助有机化学实验教学的案例研究:以乙酸乙酯合成实验为例

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Abstract

Organic chemistry is an important basic course in the field of natural science, and its experimental teaching is also an important part of this course. How can students acquire practical ability in experimental practice within the limited class hours? Our organic chemistry experimental teaching team has developed a teaching model using density functional theory (DFT) calculation-aided experimental teaching of organic chemistry. In this paper, taking the ethyl acetate synthesis experiment as an example, we provided a case study using DFT calculation-aided experimental teaching of organic chemistry. The reaction mechanism of ethyl acetate was studied using Gaussian 09 software. The changes in reaction energy barrier and carbonyl carbon structure were also studied. Our results show that the rate-determining step is the nucleophilic addition. The reasonable raw material addition procedure is that the glacial acetic acid and anhydrous ethanol should first be added to a flask, followed by adding sulfuric acid slowly. DFT calculation can explain clearly the mechanism of esterification reaction in a graphic form, which is not only helpful for the students to better grasp the key points of the experiment but also beneficial for deeply understanding the esterification reaction. It provides some important guidance and reference for the teaching activities of organic chemistry in the university and high school.

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