《Organic Chemistry》课程教学大纲
一、课程基本信息
英文名称 | Organic Chemistry | 课程代码 | PHAR1111 |
课程性质 | 专业必修课程 | 授课对象 | 药学全英文班 |
学 分 | 5 | 学 时 | 90 |
主讲教师 | 乔春华、何慧 | 修订日期 | 2021.7.27 |
指定教材 | Organic Chemistry：Paula.Y. Bruice, 7th edition | ||
二、课程目标
Organic Chemistry is a course to introduce the chemical properties of carbon containing compounds - organic compounds. Organic compounds are often referred to as organic molecules, which cover all aspects of life, including fat, carbohydrates, proteins, and nucleic acids. The task of the course is to help students to understand and master the basic knowledge of organic chemistry and the latest developments, so to form a logical and complete framework system of this discipline. The course focuses on the general concept of organic chemistry, organic/base theory, the properties of various organic functional groups. The students are expected to understand the basic principles, organic reactions and mechanisms of these reactions, and can propose rational synthetic route and carry out simple synthesis of less complex organic compounds.
Specific objectives are listed and closely related to the teaching contents for each part, as detailed in the following section.
（三）课程目标与毕业要求、课程内容的对应关系
表1：课程目标与课程内容、毕业要求的对应关系表
课程目标 | 课程子目标 | 对应课程内容 | 对应毕业要求 |
Objective1 | Knowledge learning | The principals of organic chemistry, terms, basic concepts. Functional groups and reactions, mechanism of the reaction, retro-synthetic analysis | Students are expected to understand and remember basic principles, concepts, compound types, major and basic type of reactions, be able to draw the mechanism of these reactions. |
Objective 2 | Language learning | Nomenclatures, professional words in the textbook | Improved professional English reading and understanding level |
Objective 3 | Critical thinking and problem solving | Most updated organic knowledge | Deep-learning, problem solving ability development |
三、教学内容
Section 1. Organic chemistry basic principles, including acid/base theory, isomers, electron delocalization
1.教学目标
To introduce the basic concepts in organic chemistry. Students are expected to deeply understand: (1) acid/base theory; (2) stereochemistry and chiral carbon and chiral compound knowledge; (3) electron delocalization, resonance structures
2.教学重难点
The electron delocalization theory and drawing the resonance structures
3.教学内容
(1) acid/base theory
(2) Isomers and stereochemistry
(3) Electron delocaliztion
4.教学方法
(1) Teaching method: Relevant concepts and theoretical framework.
(2) Discussion method: The use of heuristic teaching.
5.教学评价
Quick summary test and discuss selected frequently asked questions.
Section 2. Group I compounds: alkenes and alkynes, reaction type for hydrocarbon with double/triple bonds
1.教学目标
2.1 Structure feature and nomenclature of alkene and alkynes
2.2 Electrophilic addition reaction mechanism for double/triple bond
2.3 Draw the product formed from electrophilic addition reaction
2.教学重难点
2.2 Use electron flow arrow to indicate the electrophilic reaction
2.3 The addition reaction regioselectivity and stereoselectivity
2.4 the carbon cation stability---hyperconjugation
3.教学内容
2.3.1 Nomenclatures of alkenene and alkynes
2.3.2 reaction between double/triple bond with hydrogen halide, water/alcohol, halides
2.3.3 electrophilic reaction mechanism, regioselectivity and product stereochemistry issue.
2.3.4. the M-rules for addition reaction
2.3.5 Hydrogenation or reduction and oxidation reactions on the double bond/triple bond
2.3.6 Transition state, reaction intermediate concept
4.教学方法
PPT in combination with blackboard drawing and ball-stick model construction
5.教学评价
Quick summary test and discuss selected frequently asked questions.
Section 3 Group II compounds: alkyl halides, alcohols and expoxides
1.教学目标
3.1.1 Name this group of compounds
3.1.2 Substitution reaction (SN1, SN2):
3.1.3 Elimination reaction (E1, E2)
2.教学重难点
3.2.1 Use electron flow arrow to draw the reaction mechanism for substitution and elimination reactions
3.2.2 To give the correct reaction mechanism for different substrate: primary alkyl halide/alcohol, secondary alkyl halide/alcohol, tertiary alkyl halide/alcohol.
3.2.3 The stereochemistry and regiochemistry for substitution and elimination reactions.
3.2.4 Reaction of alcohol with thionyl chloride, trichlorine phosphine
3.2.5 Protective groups for alcohol
3.2.7 Oxidation reaction for alcohol, oxidants.
2.3.8. the Z-rules for elimination reaction
3.教学内容
(1) Nomenclatures for alkyl halides, alcohols and expoxide
(2) Substitution and elimination reactions.
(3) Reaction product formed between double/triple bond with alkyl halide, water/alcohol, halide, boron compounds
4.教学方法
PPT in combination with blackboard drawing, in class quiz
5.教学评价
Quick summary test and discuss selected frequently asked questions.
Section 4 Saturated hydrocarbon compounds
1.教学目标
4.1.1 Name the saturated hydrocarbons
4.1.2 Be able to draw the radical mechanism for saturated hydrocarbons
2.教学重难点
4.2.1 Radical mechanism as indicating by single electron flow
4.2.2 Radical substitution mechanism
4.2.3 Radical addition mechanism for this group of compounds
3.教学内容
4.3.1 Nomenclature of saturated hydrocarbons
4.3.2 Radical substitution reaction between saturated hydrocarbons and chlorine and bromines.
4.3.3 Radical addition reactions between double bond containing hydrocarbons and NBS
4.教学方法
Based on the introduction of case study, improve the student understanding factors including physicochemical and physiological characteristics that influence drug performance in vivo and in vitro
5.教学评价
PPT in combination with blackboard drawing, in class quiz. 2nd term exam content
Section 5. Organometallic compounds
1.教学目标
5.1.1 Students are expected to understand the carbon-carbon bond formation using metal as catalyst.
5.1.2 provide the correct product when substrates are given
2.教学重难点
5.2.1 The carbon-carbon bond formation between sp3/sp2 carbon, sp2/sp2 hybridized carbon in the presence of platinium
3.教学内容
5.3.1 Heck and Suzuki reaction
5.3.2. Ruthnium catalyzed RCM reaction
4.教学方法
PPT and homework assignment, in class practice.
5.教学评价
Quick summary test and discuss selected frequently asked questions.
Section 6. Group III compounds, carboxylic acid and derivatives, ketone and aldehydes
1.教学目标
6.1.1 Name group III compounds
6.1.2 Understand the Addition-Elimination reaction mechanism for carboxylic acid and derivatives, carbonyl structure and reactivity
6.1.3 understand the reactivity order in this family
2.教学重难点
6.2.1 Reactions for the a-carbon atom with another carbonyl containing compounds
6.2.2 The reactivity sequence and conversion from less reactive functional group to more reactive groups
6.2.3 reactions for α,β-unsaturated carbonyl compounds
3.教学内容
6.3.1 Reactions for carboxylic acid and derivatives, the addition-elimination mechanism, hydrolysis, alcoholisis, aminolysis
6.3.2 the acidity of proton on the α-carbon, reactions on the α-carbon
6.3.3 Aldehyde/ketone reaction mechanism: addition only, no elimination
6.3.4 Aldehyde/ketone reaction with several nucleophiles, including water/alcohol, amines, thiols, hydride containing reagents (LAH, NaBH4, DIBAL, et al), Grignard reagent, Gilman reagent.
6.3.5. Oxidation reaction of aldehyde and ketone, the decarboxylation reaction for carboxylic acid
6.3.6 Protective groups for carbonyl group
6.3.7 Name reactions in this group of compounds: HVZ reaction, Bayer-vinager reaction, Michael addition reaction, Robinson annulation, Dickman condensation, Gabriel amine synthesis, the aldol reaction, the aldol condensation reaction, the Claisen-condensation reaction. Inter/intra molecular reaction.
6.3.8. tautomerization concept
6.3.9 the commonly used synthons to
4.教学方法
Teaching theory PPT form, case presentation, in class practice, homework assignment
5.教学评价
Quick summary test and discuss selected frequently asked questions.
Section 7. Group IV compounds: Aromatic compounds
7.1.教学目标
7.1.1 Understand the concept of aromaticity, conjugation
7.1.2. Reactions on the benzene ring---the electrophilic aromatic substitution reaction
7.1.3 The SNAr reaction for electron deficient benzene ring
7.2.教学重难点
7.2.1 The substitute effects for the benzene reaction---formation of the first addition product stability
7.2.2 The Sandmeyer reaction
7.2.3 How existing substitute affect the compound reactivity, the directing effect of electron-donating and electron-withdrawing groups, the acidity/basicity effect of the first substitute.
7.3.教学内容
7.3.1. the nomenclature of benzene and heterocycle compounds
7.3.2 reactions on the benzene ring and side chain, especially the α position
7.3.3 the Friedel-Crafts reaction, the Sandmeyer reaction
7.3.4 the oxidation reaction on the a-position
7.3.5 How the acidity/basicity of phenol, carboxylic acid, aniline is affected by the substitutes
7.3.6. synthesis practice, synthetic route design, protective groups
7.3.7 nomenclature and reaction for aromatic heterocycles, like pyridine, pyrole, thiophene, furan and other fused aromatic rings
7.4.教学方法
A combination of in class PPT, recommended reading assignment and discussion.
5.教学评价
How well the students are involved in the class, feedback from student comments, quality of the teaching PPTs.
Section 8. Amino acid and nucleic acids
8.1.教学目标
8.1.1 master the 21 commonly essential amino acids, Zwitterionic property of amino acids, peptide and protein
8.1.2 the neucleic acid base, neucleoside, neucleotide, related DNA, RNA
8.2.教学重难点
8.2.1 construction of amide bond method
8.2.2. the ATGC structure, stability
8.2.3 the protein and DNA/RNA macro molecule
8.3.教学内容
8.3.1 nomenclature and structural property, physiochemical property of amino acids
8.3.2 formation of peptide bond---reviewing the carboxylic acid and derivative knowledge, activation of carbonyl group, reagents used to form amide bond, for example DCC
8.3.3 the neucleoside, neucleotide, neuclic acid structural feature, structure difference between RNA and DNA and explanation using chemistry knowledge, the chemistry to explain why DNA use T other than U.
四、学时分配
表2：各章节的具体内容和学时分配表
Chapter | 章节内容 | 学时分配 |
Chapter 1 | Electronic structure and bonding. | 3 |
Chapter 2 | Acids and Bases | 3 |
Chapter 3 | An Introduction to Organic compounds: Nomenclature, physical properties, and representation of structure | 4 |
Chapter 4 | Isomers: the arrangement of atoms in space | 3 |
Chapter 5 | Alkanes: structure, Nomenclature, and introduction to reactivity. Thermodynamics and Kinetics | 3 |
Chapter 6 | The reactions of alkenes: The stereochemistry of addition reactions | 4 |
Chapter 7 | The Reactions of alkynes: An introduction to multistep synthesis | 4 |
Chapter 8 | Delocalized electrons and their effect on stability, pKa, and the products of a reaction | 4 |
Chapter 9 | Substitution reaction of alkyl halides | 4 |
Chapter 10 | Elimination reaction of alkyl halides | 4 |
Chapter 11 | Reactions of alcohols, ethers, epoxides, amines and thiols | 4 |
Chapter 12 | Organometallic compound | 5 |
Chapter 13 | Radicals Reaction of Alkanes | 4 |
Chapter 14 | Reactions of carboxylic acids and carboxylic derivatives | 5 |
Chapter 15 | Reactions of aldehydes and ketones: more reactions of carboxylic acid derivatives | 4 |
Chapter 16 | Reactions at the a-carbon of carbonyl compounds | 6 |
Chapter 17 | Reactions of Benzene and Substituted Benzenes | 5 |
Chapter 18 | More About Amines，Reactions of Heterocyclic Compounds | 3 |
Chapter 19 | The Organic Chemistry of Amino Acids, Peptides, and Proteins | 4 |
Chapter 20 | The Chemistry of the Nucleic Acids | 4 |
五、教学进度
表3：教学进度表
Week | Chapter | 内容提要 | 授课时数 | 作业及要求 | 备注 |
1 | Chapter 1-2 | 1. Electronic structure and bonding. 2. Acids and Bases | 6 | Home work assignment after each lecture | 1st Exam after Chapter 5. 2nd Exam after Chapter 11 3rd Exam(final exam) for chapter 11-16; Final exam cover chapter 17-20 |
2 | Chapter 3 | 3. An Introduction to Organic compounds: Nomenlature, physical properties, and representation of structure | 4 | ||
Chapter 4 | Isomers: the arrangement of atoms in space. | 2 | |||
3 | Chapter 5 | Alkanes: structure, Nomenclature, and introduction to reactivity. Thermodynamics and Kinetics | 6 | ||
4 | Chapter 6 | The reactions of alkenes: The stereochemistry of addition reactions | 6 | ||
5 | Chapter 7 | The Reactions of alkynes: An introduction to multistep synthesis | 4 | ||
6 | Chapter 8 | Delocalized electrons and their effect on stability, pKa, and the products of a reaction | 4 | ||
7 | Chapter 9 | Substitution reaction of alkyl halides | 4 | ||
8 | Chapter 10 | Elimination reaction of alkyl halides | 4 | ||
9 | Chapter 11 | Reactions of alcohols, ethers, epoxides, amines and thiols | 4 | ||
10 | Chapter 12 | Organometallic compound | 4 | ||
11 | Chapter 13 | Radicals Reaction of Alkanes | 4 | ||
Chapter 14 | Reactions of carboxylic acids and carboxylic derivatives | 5 | |||
12 | Chapter 15 | Reactions of aldehydes and ketones: more reactions of carboxylic acid derivatives | 5 | ||
13 | Chapter 16 | Reactions at the a-carbon of carbonyl compounds | 5 | ||
14 | Chapter 17 | Reactions of Benzene and Substituted Benzenes | 5 | ||
15 | Chapter 18 | More About Amines Reactions of Heterocyclic Compounds | 3 | ||
16 | Chapter 19 | The Organic Chemistry of Amino Acids, Peptides, and Proteins | 4 | ||
17 | Chapter 20 | The Chemistry of the Nucleic Acids | 4 |
六、教材及参考书目
1. Organic Chemistry, Clayden. Greeves, Warren and Wothers, OxfordUniversity Press, 2001。
2. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry Editor： Paul M. Dewick
3. Advanced Organic Chemistry ( 5th Ed)， Smith, Michael B. and Jerry March
七、教学方法
1. Teaching method: Teaching the basic concepts and principles of this course in class using PPT and video, etc.
2. Homework assignment after each lecture.
3. Discussion and self-taught. The heuristic teaching method will be employed in the class, and flipping classroom will be used 1-2 times to encourage student to actively involved in the learning process.
八、考核方式及评定方法
（一）课程考核与课程目标的对应关系
表4：课程考核与课程目标的对应关系表
课程目标 | 考核要点 | 考核方式 |
Knowledge learning | Drug structure, mechanism of action, metabolism, side effects | Quiz, homework, section exams |
Language learning | Terms, basic concepts | Extending reading |
Critical thinking training | Problem solving ability | In class challenging and writing |
（二）评定方法
平时成绩：10%，三次过程化考核考试：各占20%，期末考试30%.
（三）评分标准
90-100 | 80-89 | 70-79 | 60-69 | ＜60 |
优 | 良 | 中 | 合格 | 不合格 |
A | B | C | D | F |
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