‘Practical of Organic Chemistry’Course Syllabus
Course Category：Major Basic
Majors：Intensive Training Class
Total Hours：72 Hours Credit：3
Lecture Hours：0 Hours Lab Hours：72 Hours
Textbooks：Experimental Organic Chemistry（edited by Shaoqiong Zeng）(3nd Edtion)
References：1. “Experimental Organic Chemistry” published by Perkin University Press; 2. “Experimental Organic Chemistry” compiled by Jian Cao and Lingxiang Guo, published by Nanjing University Press, 2009
Students will learn basic yet important techniques in organic chemistry, including melting point determination, atmospheric pressure distillation, vacuum distillation, boiling point determination, recrystallization, extraction, chromatography, steam distillation and operation under anhydrous conditions. Organic compounds will be synthesized in small scale through classical experiments, e.g., substitution, dehydration, Friedel-Crafts, Ullmann, Cannizzaro, Claisen condensation, oxidation, esterification, and nitration reactions. Students will learn how to conduct experiments, and how to separate and purify organic compounds. Besides synthesis, property study is also included in organic practical. Students will learn properties of compounds such as alcohols, phenols, aldehydes, ketones, carboxylic acids and their derivatives, amines, carbohydrates, amino acids and proteins, familiarize themselves with simple methods to differentiate and identify these compounds, and reinforce textbook concepts. After each experiment, students will do data analysis, and write reports.
Through doing practical, students will understand better basic theories of organic chemistry, and their skills on conducting experiments, data analysis and problem-solving will get developed.
Chapter One Preparation of 2-furfuryl alcohol and 2-furoic acid
1Prepare 2-furfuryl alcohol and 2-furoic acid through Cannizzaro reaction
2Isolate 2-furfuryl alcohol and 2-furoic acid through distillation and recrystallization, respectively
1 What is the principle of Cannizzaro reaction?
Chapter Two Preparation of ethyl acetoacetate
1Prepare ethyl acetoacetate through Claisen condensation
2Conduct reactions under anhydrous conditions
3Isolate ethyl acetoacetate through vacuum distillation
1What is the principle of Claisen condensation?
2How to prepare sodium beads?
Chapter Three Properties of carboxylic acids and their derivatives
1Properties of carboxylic acids and their derivatives
2Preparation and properties of soap
Chapter Four Preparation of adipic acid
1 Prepare adipic acid through oxidation of cyclohexanol
2 Learn the NO2 gas trap setup
1 What is the principle of the oxidation reaction?
2 How to trap toxic NO2 gas?
Chapter Five Preparation of diethyl adipate
1Prepare diethyl adipate through esterification reaction
2 Use Dean-Stark trap and vacuum distillation
1What is the principle of the esterification reaction?
2 How to push an equilibrium to completion?
Chapter Six Preparation of o- and p-nitroanilines
1Prepare o- and p-nitroanilines through nitration reaction
2 Separate o- and p-nitroanilines through steam distillation
1What is the principle of the nitration reaction of aromatic compounds?
2What is the principle and application of steam distillation?
Chapter Seven Properties of amines
1Properties of aliphatic and aromatic amines
2Differentiate primary, secondary and tertiary amines
Chapter Eight Alkaloids (caffeine) extraction
1 Extract caffeine from tea leaves using Soxhlet extractor
2 Purify caffeine through sublimation
1 What is the principle of the nitration reaction of Soxhlet extractor?
2 What is the principle and application of sublimation?
Chapter Nine Preparation of triyl alcohol
1Prepare Grignard reagent under anhydrous condition
2Prepare triyl alcohol through reaction of benzophenone and Grignard reagent
1What is Grignard reagent and its application in organic synthesis?
2How to prepare Grignard reagent under anhydrous condition?
Chapter Ten Preparation of poly(vinyl formal)
1 Prepare poly(vinyl formal) through acetalization of polyvinyl alcohol
2 Use mechanical stirrer
1What is the setup and operation of mechanical stirrer?
Chapter eleven Properties of carbohydrates, amino acids and proteins
1Properties of carbohydrates, amino acids and proteins
2 Differentiate carbohydrates, amino acids and proteins
Evaluation will be based on performance on each experiment and final exam, amounting to 70% and 30%, respectively.
Performance on each experiment will be assessed based on pre-lab report, experiment conduct, lab report and results. Lab reports should contain principles, procedures (process chart), main setup diagrams, data records, results and discussions, and conclusions.
The final examination will involve a number questions related to practical, and conducting certain experiment that was done during practical.
Made by ：Yuan Dan
Date: Nov. 5th, 2016