清华大学有机化学李艳梅课件(全)第1章

The demise of vitalism
1828, preparation of urea from inorganic compounds indicates the demise of “vitalism”.
By the 18th century, some pure organic compounds were obtained.
Schorlemmer’s definition 肖莱马的定义
Based on chemical structural theory, Schorlemmer defined organic compound as “ hydrocarbon and its derivatives”, and organic chemistry as “chemistry of hydrocarbon and its derivatives”.
O HH
甲醛
Wine was invented before Xia dynasty. By Zhou dynasty, wine has become very important in sacrifice events.
制酒
CH3CH2OH «周礼»
Vinegar production has already become an expect technology by Zhou dynasty.
(from Yale University)
1800
A brief history
Friedrich Wöhler Synthesis of urea
1900
2000
Important events on organic chemistry
1828 Synthesis of urea, indicating demise of vitalism Milestone of organic chemistry By Wöhler
Content
Part I Organic compounds and organic chemistry ------ History
第一部分 有机化合物与有机化学 －－ 历史简介
Part II Fundamental Knowledge 第二部分 基础知识 ● Structure, reaction & Classification ● Formulas ● Nomenclature ● NMR, IR, UV & MS
Means of “Organic chemistry” “有机化学”的含义
1806
First citing 基于 “生命力”学说
Based on “vitalism”, Berzelius first cited this word, and deemed organic compounds could not be produced without the special power “vita force”.
In 1845 acetic acid and in 1854 ester were separately synthesized from inorganic compounds, indicating the final demise of vitalism.
兴趣阅读：
See appendix file 0001: Letter between Wöhler and his adviser, Berzelius. See appendix file 0002: Wöhler’s paper on synthesis of urea See appendix file 0003: Problems and answers on the urea synthetic paper
有机化学A1
主讲教师：李艳梅 教授 清华大学化学系
E-mail: liym@tsinghua.edu.cn URL: http://chem.tsinghua.edu.cn/liym
Introduction 第一章 绪论
Organic Chemistry A (1) By Prof. Li Yan-Mei Tsinghua University
有机化学研究领域
1.4 The methods to study organic chemistry and how to learn organic chemistry
有机化学研究方法及如何学习有机化学课程
1.1 Introduction and a brief history
有机化学历史简介
有机化学 ？
有机化学研究方法及如何学习有机化学课程
1.2 Character of organic compound 有机化合物的特性
结构上
1、碳通常以共价键与其它原子相连 C N C O C Cl C I
CS CF 2、自身成键能力强
C Br
CC CC CC 3、同分异构现象普遍存在
CP
化学性质
物理性质
Chemical Properties
1.2 Character of organic compound
有机化合物的特性
1.3 Research fields in organic chemistry
有机化学研究领域
1.4 The methods to study organic chemistry and how to learn organic chemistry
“碳氢化合物及其衍生物”
Hint
分类的关键： “性质”！ 而不是“组成”
H HNH
BB NN HBH
H
1. Organic compounds and organic chemistry 第一部分 有机化合物和有机化学
1.1 Introduction and a brief history
有机化学历史简介
Definition 元素分析结果
A.L. Lavoisier and Von Liebig J.F. invented the elemental analysis protocal. They found all organic compounds contain carbon, most contain hydrogen, many contain oxygen and nitrogen.
有机化学研究领域 • Nature Product Chemistry 天然产物化学
Separated, or extracted chemicals from nature products. Eg. Hormones, Auxin, Pheromone
Turtric acid was obtained from grape juice, citric acid was abstracted from lemon juice, and urea was purified from urine.
In 1806, famous chemist, Berzelius J. first used the word “organic chemistry”, and states, organic compounds could not be produced without “vital force（生命力）”
1.3 Research fields in organic chemistry
有机化学研究领域
1.4 The methods to study organic chemistry and how to learn organic chemistry
有机化学研究方法及如何学习有机化学课程
1.3 Research fields in organic chemistry
稳定性不如无机物 Less stable 易燃 Inflammation
反应速度慢 Low reaction rate 副反应多 Frequent side reaction
Physical Properties
Low melting point 熔点低 Low boiling point 沸点低 High volatility 挥发性大 Often insoluble 多数难溶于水 Density often lower than water
比重一般比水小
1. Organic compounds and organic chemistry 第一部分 有机化合物和有机化学
1.1 Introduction and a brief history
有机化学历史简介
1.2 Character of organic compound
有机化合物的特性
1. Organic compounds and organic chemistry 第一部分 有机化合物和有机化学
1.1 Introduction and a brief history
有机化学历史简介
1.2 Character of organic compound
有机化合物的特性
1.3 Research fields in organic chemistry
1865 Bringing forward that carbon is quadrivalent
Milestone of structural theory By A. Kekulé
1874 Saturated carbon atoms share tetrahedral topology
Initiation of stereochemistry By J.H.Van’t Hoff
1865
Kekülé and Gmelin defined organic chemistry as “chemistry of carbonaceous compounds”
将“有机化合物”定义为“含碳的化合物”，则“有机化学”即为 “研究含碳化合物的化学”
Of course, many carbonaceous compounds are not organic compounds
(NH4)+NCO氰酸铵
Ammonium cyanate
H2N NH2 O
The fact that organic compounds could be obtained from inorganic compounds without the help of organism was not accepted for a long time.
制醋
H3C C OH O
Dyeing has become am important industry before Zhou dynasty.
茜 草
染色
In ancient ages, mixtures of organic compounds were abstracted from natural products. Chinese traditional drug, dye, and perfume are of this kind.
Initiation of stereochemistry By J.A.Le Bel 1917 Lewis acid and Lewis base theory
1931
Milestone of structural theory By Lewis Huckel rules The Frontier-orbital theory The principle of conservation of orbital symmetery
Organic Chemistry in the History
古埃及人利用有机化合物处理尸体
To make human body into a mummy,
formalin was often employed in ancient Egypt.
Formalin aqueous solution of formaldehyde
有机化合物 ？
Starch（淀粉）
O
OH
H
* C R1 C N R2 N n*
Gasoline （汽油）
CmHn m value around 8
O OH
O O CH3
乙酰水杨酸（阿斯匹林）
O OH
OH
Salicylic acid
H3C C O C CH3 OO
O OH
O O CH3
AΒιβλιοθήκη Baiduetylsalicylic acid