有机化学

Xi'an Jiaotong University via Coursera

Go to Course: https://www.coursera.org/learn/organic-chemistry

Introduction

### Course Review: 有机化学 (Organic Chemistry) **Overview** The course titled 有机化学 (Organic Chemistry) on Coursera presents an extensive introduction to the study of organic compounds, delving into their structures, properties, mutual conversions, and underlying principles. It is a core requirement for undergraduate chemistry students and serves as a prerequisite for advanced studies in biochemistry, molecular biology, medicine, and pharmacy. This course holds significant importance within the educational curriculum, providing a solid foundation for further specialized learning. The curriculum covers a broad spectrum of organic compounds, including alkanes, alkenes, aromatic hydrocarbons, haloalkanes, alcohols, phenols, ethers, aldehydes, ketones, carboxylic acids and their derivatives, amines, and heterocycles. Special attention is given to the properties, inter-conversions, and mechanistic studies of these compounds, alongside a thorough exploration of stereochemistry and basic spectroscopy. Through this course, learners will acquire the knowledge necessary to understand the structure, nomenclature, and properties of common organic compounds. They will gain insights into the transformation of functional groups, mechanisms of typical organic reactions, and the design of simple synthetic pathways, reinforcing their understanding of organic chemistry in preparation for more advanced studies. **Course Structure** The course is designed to be engaging and interactive, consisting of short video lectures (5-15 minutes each) interspersed with 1-2 quiz questions to enhance learning. At the end of each chapter, approximately ten unit exercises are provided, and a comprehensive final exam assesses the knowledge acquired throughout the course. **Prerequisites** To enroll in the course, students should possess a foundational understanding of high school chemistry, as well as basic knowledge of inorganic or general chemistry at the university level. ### Detailed Breakdown of Course Modules 1. **Introduction to Organic Chemistry** This module establishes the basic definitions and characteristics of organic compounds. Key topics include the types of covalent bonds, mechanisms of bond breaking, and the classification of organic compounds. 2. **Alkanes and Cycloalkanes** Explore the structure, naming conventions, and properties of alkanes and cycloalkanes. The module addresses the stability of different conformations and discusses reaction mechanisms. 3. **Alkenes and Alkynes** Focused on the structural characteristics of alkenes and alkynes, this module covers electrophilic addition reactions and the electronic effects influencing these reactions. 4. **Basics of Spectroscopy** An introduction to organic spectroscopy, including NMR, IR, UV-Vis, and mass spectrometry, with a focus on analyzing organic structures through these methods. 5. **Aromatic Compounds** Study the nomenclature and electrophilic substitution reactions of aromatic compounds, including the concept of aromaticity. 6. **Stereochemistry** This module covers essential concepts in stereochemistry, including chirality and the rules for drawing Fischer projections and assigning configurations. 7. **Haloalkanes** Learn about the structure, classification, and reactions of haloalkanes, including nucleophilic substitution and elimination mechanisms. 8. **Alcohols, Phenols, and Ethers** Examine the structures and properties of alcohols, phenols, and ethers, exploring their distinctive features and reactions. 9. **Aldehydes and Ketones** Investigate the structure and reactivity of aldehydes and ketones, focusing on nucleophilic addition and condensation reactions. 10. **Carboxylic Acids and Derivatives** This module provides an overview of carboxylic acids, their derivatives, and the mechanisms of nucleophilic acyl substitution. 11. **Amines and Heterocycles** The final module details the structures, classifications, and reactions of amines and heterocyclic compounds, discussing their unique properties and behaviors. ### Recommended Reading 1. 唐玉海主编，《有机化学》，化学工业出版社，2011 2. 邢其毅主编，《基础有机化学》，高等教育出版社，2009 3. John E. McMurry, "Organic Chemistry" ### Recommendation The 有机化学 (Organic Chemistry) course on Coursera is highly recommended for anyone pursuing a career in the sciences, particularly in chemistry, biochemistry, or related fields. The structured approach, engaging video content, and interactive assessments make the learning process both comprehensive and enjoyable. This course lays a strong foundation in organic chemistry that will benefit students in their academic and professional pursuits. Whether you are a beginner or looking to refresh your knowledge, this course will equip you with essential skills and insights into the fascinating world of organic compounds. Enroll now and enhance your understanding of this critical discipline in the realm of science!

Syllabus

绪论

欢迎学习有机化学，有机化学是研究各类有机化合物的结构、性质、相互转化及其规律的一门学科。在本模块中你将学习什么是有机化学，什么是有机化合物；有机化合物有哪些特点；共价键有几种类型？σ键和π键是如何形成的，各自有何特点；共价键的断裂方式有几种；不同断裂方式对应哪种反应类型，以及有机化合物该如何分类等知识重点。

烷烃和环烷烃

本模块将重点介绍烷烃和环烷烃的结构、命名、性质。请你带着这些问题学习本模块内容：烷烃的命名方法是什么；什么是构象？何谓优势构象？环己烷什么构像最稳定；烷烃自由基取代反应的机制是什么；环烷烃与烷烃的化学性质有何异同；环烷烃稳定性与环的大小有何关系。

烯烃和炔烃

本模块将重点介绍烯烃、炔烃和共轭二烯烃的结构特征，烯烃的亲电加成反应及机理，电子效应等知识。请你带着这些问题学习本模块内容：如何标记碳碳双键的构型；什么又是烯烃的亲电加成反应？其机理是什么；烯烃和炔烃在化学性质上有哪些异同点；什么是马氏规则；何为诱导效应和共轭效应。

波谱学基础

本模块将介绍有机波谱学的基本知识，包括核磁共振波谱、红外吸收光谱、紫外吸收光谱和质谱。请你带着这些问题学习本模块内容：何为有机化学四大波谱？它们在有机物结构鉴定方面主要解决什么问题；核磁共振发生的条件是什么？核磁氢谱的主要参数有哪些？如何解析核磁氢谱；影响分子振动吸收频率的主要因素有哪些；具有什么结构特征的化合物具有紫外吸收现象；质谱的原理又是什么？

芳香化合物

本重点介绍苯的结构、芳香烃的亲电取代反应及机制、亲电取代反应的定位效应、非苯性芳烃及Hückel规则。请你带着这些问题学习本模块内容：芳香烃是如何命名的；芳香烃的结构特点是什么；芳香性的含义是什么；怎样判断化合物分子是否具有芳香性；苯环上亲电取代反应的定位效应是什么？其原因又是什么？

立体化学

本模块将重点介绍立体异构中所涉及的一些基本概念。请你带着这些问题学习本模块内容：什么是旋光异构体？什么是旋光度、比旋光度；手性、手性分子、手性碳原子、对映异构体、非对映体、内消旋体、外消旋体分别是什么含义；分子的对称因素与手性有何关系？如何判断化合物是否具有旋光性；Fischer投影式的书写规则是什么；旋光异构体构型的标记方法有几种？又是如何标记的呢？

卤代烃

本模块将介绍卤代烃结构、类型及其反应，并重点介绍SN1、SN2、E1、E2反应及其机制。SN和E的竞争性反应等知识。请你带着这些问题学习本模块内容：卤代烃的分类方法有几种；伯卤代烃与叔卤代烃发生的亲核取代反应机制有什么不同；卤代烃的消除反应有什么规律？不同结构卤代烃发生消除反应的活性大小顺序如何；亲核取代反应和消除反应的竞争受哪些因素的影响；乙烯型卤代烃和烯丙型卤代烃发生亲核取代反应的活性有何不同？为什么？

醇、酚、醚

本模块将醇、酚、醚的基本结构、命名和性质。请你带着这些问题学习本模块内容：醇的卤代及脱水反应中，为什么会出现分子重排产物；邻二醇都有哪些特性；酚的结构有什么特点？酚羟基与醇羟基有什么不同；鉴别醇和酚都有哪些方法；醚键是如何断裂的？取代环氧乙烷的开环反应有何规律？

醛、酮、醌

本模块将重点介绍醛、酮、醌的结构和命名、醛酮的亲核加成反应、缩合反应、氧化还原反应等知识。请你带着这些问题学习本模块内容：醛、酮和醌在结构上有何联系与区别；醛酮亲核加成反应的机理与烯烃亲电加成反应的机理有何不同；不饱和醛酮的亲核加成反应是怎样进行的；什么是碘仿反应？羟醛缩合反应发生的条件是什么；醌的结构决定了它有哪些化学性质？

羧酸及其衍生物

本模块将重点介绍羧酸及其衍生物的结构、分类和命名，羧酸的酸性及其影响因素，羧酸衍生物的亲核取代反应及其机制等知识。请你带着这些问题学习本模块内容：羧基中存在什么类型电子效应；羧酸的酸性强弱取决于哪些因素，有何规律；不同二元酸受热时所发生的反应有何差异；羧酸衍生物的水解、醇解和氨解属于什么反应类型？它们的活性次序如何；什么是Claisen酯缩合反应？什么类型的酯才能进行该反应。

胺和杂环

本模块将重点介绍胺和杂环化合物的结构、分类、命名及性质。请你带着这些问题学习本模块内容：伯、仲、叔胺的化学性质有何异同之处？如何鉴别；影响胺类碱性强弱的因素有哪些；胺和酰胺的化学性质有什么不同；为什么吡咯有一定的酸性而吡啶却显碱性；为什么吡啶既能发生亲电取代又能进行亲核取代反应。