Course Code: B32012H-01
Course Name: Experiments on Organic Chemistry
Pre-requisite: Organic Chemistry
Lecture Time: 80 hours
This course is a compulsory course for undergraduates majoring in chemistry and related subjects.It can also be selected by undergraduate students who major in material science and engineering, chemical engineering and technology, life science and other related subjects.
Chemistry is the subject of creating materials, andthe synthesis and separation of organic chemistry experiments are the basic process and the means to create the most original organic matter.The use of various analytical instruments is a necessary means to judge the structure and properties of new materials.Through the teaching of organic chemistry experiment, we hope to achieve the following goals:
1) Deepen the understanding of the basic theoretical knowledge of organic chemistry, the basic nature of organic compounds, organic reaction and mechanism, and the safety of organic substances;
2) Train students to master the basic operating skills of organic chemistry experiments, training students to improve their ability and safety awareness;
3) Basic principles and preliminary application of related instruments and equipment;
4) To cultivate students' ability of experimental design, synthesis, purification, structure identification and characterization of the judgment,improve the comprehensive ability of analysis and solving the problem, andlay a good foundation for future study of specialized courses and scientific research.
5) To cultivate students' scientific attitude of seeking truth from facts, rigorous and detailed observation, good laboratory work habits.To guide students to put forward scientific exploration problems, to stimulate students' scientific interest and innovative consciousness.
Before the experiment, students should be aware of the performance of related organic compounds.Students are required to learn the physical and chemical constants of organic compounds by using the related manuals, documentation and information network.
Students should be required to deal with the performance of related organic compounds and before the experiment carefully prepared to write a preview report;In the course of the experiment, carefully observe the experimental phenomenon and carefully record, analyze and collate data;after class, according to the requirements, write the experimental report.Teachers will investigate students’ preview of class, equipment, basic operation, product quality and quantity, safety, health, scientific attitude, cooperation spirit, experimental reports and other aspects, and this will be used as a basis for students' scores.
The study of this course willimprove the students' learning and organic chemistry experiment and research of the basic knowledge of Organic Chemistry,lead students to the field of Organic Chemistry,improve the comprehensive quality of solving practical problems in the field of Organic Chemistry, and lay the foundation for the cultivation of professional talents of the subject.
Topics and Schedule
Part 1:Preface and main instrument training (~8 hours)
Preface: General knowledge of organic chemistry experiments and introduction of laboratory safety techniques (2 hours)
Aims and requirements:Learn about the general knowledge of organic chemistry experiments, including safety and hygiene.Must be prepared before the experiment, the experiment must be recorded in the process, as well as the correct writing of the experimental report, etc.
Laboratory instrumentation and presentation training (6 hours) (This part introduces the general principle of the instrument operation, the use of equipment)
Aims and requirements:Understand the basic principles of different instruments,after basic training, the students can choose to use different instruments according to the needs of specific experiment,test different types of organic compounds.The structure of the organic matter is inferred by using different spectral data and determine the purity and quality of the related substances.
Part 2: Basic operating skills (~8 hours)
Master: distillation, recrystallization, filtration, boiling point and melting point determination.
Experiment 1:Crystallization purification and determination of melting point of solid samples (4 hours)
Aims and requirements:Principle and method for the purification of solid organic compounds by recrystallization;Master folding filter paper, pumping filtration,hot filtration and other basic operations;Understand the significance of the determination of melting point, grasp the principle and method of measuring the melting point.
Instrument and equipment:oven, circulating water pump, digital display electric heating sleeve, and micro melting point measuring instrument
Experiment 2:reduced pressure distillation (4 hours)
Aims and requirements:Understand the relationship between boiling point and vacuum degree,master the principles and methods of reduced pressure distillation.
Instrument and equipment:vacuum pump, vacuum pressure gauge, thermometer, distilled glass instrument set
Part 3: Separation and synthesis experiment (~64 hours)
Separation experiment is an important part of organic chemistry experiment, and it is the most important early stage of organic synthesis;students can be trained to isolate and purify compounds.Only with a very skilled compound separation skills,can we guarantee the purity of the synthesized compounds and provide a material guarantee for the structure and performance of organic matter.
The synthetic experiment is the main part of the organic chemistry experiment. When we choose synthetic experiments,the basic operation to obtain a more comprehensive and repeated training should be taken into account.Students should be made to do a number of different types of synthetic reaction experiments.The choice of each experiment has certain representatives and a purpose, students should select some comprehensive synthetic experiments and designing experiments.The results of the experiment are analyzed and tested by students, which can improve the ability of comprehensive training, analysis and problem solving.This will lay the foundation for students in the future to design and implement the goal of the synthesis of the compound by combining with the theoretical knowledge of reference.
Experiment 3:The principle and method of thin layer chromatography (TLC) and the separation and extraction of pigment (8 hours)
Aims and requirements:Understand the principles of thin layer chromatography for the separation of organic compounds;Master the preparation methods of thin layer chromatography and the basic skills of thin layer chromatography for the separation of organic compounds.Through the extraction and separation of green plant pigment, understand the basic idea of the method of separation and extraction of natural substances and the specific process of the implementation of the experiment;through thin layer chromatography and column chromatography separation operation, deepen the understanding of trace organic matter chromatography separation identification principle.
Instrument and equipment:Ultraviolet fluorescent lamp, circulating water pump, rotary evaporation apparatus, vacuum drying box, ultraviolet spectrum instrument (UV)
Experiment 4:1- bromide synthesis (8 hours)
Aims and requirements:Learn the principles and methods of preparing 1- bromine, and master the reflux operation with absorbing harmful gases.
Instrument and equipment:Magnetic heating agitator, vacuum pump, rotary evaporation apparatus, gas chromatograph (GC)
Experiment 5:Preparation of adipic acid from cyclohexanol (8 hours)
Aims and requirements:Study the principle and method of preparation of adipic acid, consolidate the recrystallization of the operation
Instrument and equipment:Magnetic heating agitator, thermometer, circulating water pump, rotary evaporation instrument, infrared spectrometer (IR) or Raman spectrometer (Raman)
Experiment 6:Aniline synthesis (8 hours)
Aims and requirements:Process for the reduction of aromatic nitro compounds to amines
Instrument and equipment:Magnetic heating agitator, rotary evaporator, gas chromatograph (GC), infrared spectrometer (IR) or Raman spectrometer (Raman)
Experiment 7: Synthesis of methyl orange (8 hours)
Aims and requirements:Process for preparing dye and azo compounds.
Instrument and equipment:Magnetic heating agitator, rotary evaporation apparatus, high performance liquid chromatograph (HPLC), nuclear magnetic resonance instrument (NMR).
Experiment 8:Resolution of DL-benzene (8 hours)
Aims and requirements:Study the resolution method of the mixture of DL, and consolidate the operation of recrystallization.
Instrument and equipment:Rotary evaporator, vacuum pump, polarimeter
Experiment 9: Anti-1, 2-diphenylethene
Aims and requirements:Preparation of anti-1, 2-diphenylethene by Wittig reaction.
Instrument and equipment:Magnetic heating agitator, oil bath, circulating water pump, drying oven, rotary evaporation apparatus, ultraviolet fluorescent lamp, fluorescence spectrometer (FL), or ultraviolet absorption spectrometer (UV), or nuclear magnetic resonance spectrometer
Experiment 10: Emulsion polymerization of polystyrene (8 hours)
Aims and requirements:Study the basic principles of emulsion polymerization,master the principles and methods of gel permeation chromatography for the determination of molecular weight.
Instrument and equipment:Magnetic heating agitator, constant temperature device, oil bath, nitrogen gas device, circulating water pump, vacuum drying box, gel permeation chromatograph (GPC).
Wang Qinglian (Lanzhou University), organic chemistry experiment (Third Edition), higher education press, 2010
Institute of organic chemistry, School of chemistry, Peking University, "organic chemistry experiment" (Second Edition), Peking University press, 2002
Li Zhaolong, Yin Jin, organic chemistry experiment, Tsinghua University press, 2001
Tietze, L. F.; Eicher, T.; Diederichsen, U.; Speicher, A.; Reactions and Syntheses in the Organic Chemistry Laboratory, Wiley (2007)
B.S.Furniss et al., Vogel’s Textbook of Practical Organic Chemistry, 5th ed (1989), Pearson Edu.Limited. vol1, vol2. ISBN: 7-5062-6584-2/O, 7-5062- 6585-0/O.2004
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