厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）第十章 羧酸 Carboxylic Acids（10.1-10.4）

第十章駿羧灣 rbo lc Acids

第十章羧酸 Carboxylic Acids

COoH carboxyl R--C-OH Carboxylic acids occupy a central place E. among acyl derivatives. Not only are they important compounds themselves, they also serve as building blocks for preparing related derivatives such as esters and amides. Among important examples are a cholic acid, a major component of human bile, and long-chain aliphatic acids such as a oleic acid and linoleic acid, which are a biological precursors of fats and other lipids

Organic Chemistry Organic Chemistry Xiamen Xiamen University University R C O OH COOH c a rboxy l Carboxylic acids occupy a central place among acyl derivatives. Not only are they important compounds themselves, they also s erve as building blocks for preparing related derivatives such as esters an d amides. Among important exa mples ar e cholic acid, a major component of human bile, and long-chain aliphatic acids such as oleic acid and linoleic acid, which ar e biological precursors of fats and other lipids

自然界中的羧酸 COOH OH H C=C HO OH CH3(CH2)Y(CH2),COOH 胆酸( Cholic acid) 油酸( Oleic acid) HH ①D H C=C C=C CH3(CH2)4 CH (CH2)COOH ⑨D 亚油酸( Linoleic acid)

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 自自 然然 界界 中中的羧酸 的羧酸 HO OH OH COO H






































胆酸 (Cholic acid ) C C CH 3(C H 2 ) 7 (C H 2 ) 7COOH H H 油酸 ( Oleic acid ) C C CH 3 CH 2 (CH 2 ) 4 H H C C (CH 2 ) 7COOH H H 亚油酸 ( Linoleic acid )

9 Many simple saturated carboxylic acids are e. also found in nature. For example, acetic o acid is the chief organic component of g vinegar; butanoic acid is responsible for the Ei rancid odor of sour butter, and hexanoic acid (caproic acid) is responsible for the unmistakable aroma of goats and dirty gym socks CH3 COOH CH3 CH, CH COOH 惜酸 丁酸 Acetic acid Butanoic acid

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Many simple saturated carboxylic acids are also found in nature. For example, acetic acid is the chief organic component of vinegar; butanoic acid is responsible for the rancid odor of sour butter; and hexanoic acid (caproic acid) is responsible for the unmistakable aroma of goats and dirty gym socks. CH 3COOH CH 3CH 2CH 2COOH 醋酸 丁酸 Acetic acid Butanoic acid

9g 10.1羧酸的分类和命名 Classification and Nomenclature of Carboxvlic Acids

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 10.1 羧酸的分 类 和 命 名 Classification and Nomenclature of Carboxylic Acids

10,11羧酸的分类 (Classification 引按烃基分类 饱和脂肪酸 脂肪酸 羧酸 不饱和脂肪酸 芳香酸 按羧基数目分类 一元酸、二元酸、多元酸

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 10.1.1 羧酸的分类 (Classification) 按烃基分类 脂肪酸 饱和脂肪酸 不饱和脂肪酸 芳香酸 羧酸 按羧基数目分类 一元酸 二元酸 多元酸

1012羧酸的命名 (Nomenclature) 系统命名 云将相应的烃名改为某酸,羧基始终编为1号; 若主链含烯键→某烯酸;>Cω→某碳烯酸 羧基直接连接在环上的 烃名十羧酸——脂肪酸 烃名十甲酸——芳香酸 r俗名 根据其来源命名,如: 」蚁酸、醋酸、草酸、软脂酸、硬脂酸

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 系统命名 将相应的烃名改为某酸 羧基始终编为 1 号 ; 若主链含烯键 某烯 酸 >C10 某碳 烯 酸 羧基直接连接在环上的 : 烃名 羧酸 —— 脂肪酸 烃名 甲酸 —— 芳香酸 10.1.2 羧酸的命 名 (Nomenclature) 俗名 根据其来源命名 如 蚁酸 醋酸 草酸 软脂酸 硬脂酸

d Nomenclature of Carboxylic Acids Carboxylic acids that are derived from openchain alkanes are systematically named by replacing the terminal -e of the corresponding alkane name with -oic acid Compounds that have a --CooH group g bonded to a ring are named using the g suffix-carboxylic acid. The carboxylic acid carbon is attached to c1 and is not itself o numbered in this system

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Nomenclature of Carboxylic Acids Carboxylic acids that are derived from openchain alkanes are systematically named by replacing the terminal –e of the corresponding alkane name with –oic acid. Compounds that have a —COOH group bonded to a ring are named using the suffix –carboxylic acid. The carboxylic acid carbon is attached to C1 and is not itself numbered in this system

CH CH3 CHCh2 Ch2c--oh 4-甲基戊酸 4-Methylpentanoic acid CH2CH3 CH3 O Ho-CCHoCHCHoCHoCHCHoC-OH 3-甲基-6-乙基辛二酸 3-Ethyl-6-methyloctanedioic acid

Organic Chemistry Organic Chemistry Xiamen Xiamen University University CH 3CHCH 2CH 2 C O OH CH 3 4-甲基戊酸 4-Methylpentanoic acid CC H 2CHCH 2CH 2CH C H 2 C O OH O CH 3 HO CH 2CH 3 3-甲基-6-乙基辛二酸 3-Ethyl-6-methyloctanedioic acid

COOH 2 3-溴环己烷羧酸 4 Br 3-Bromocyclohexanecarboxylic acid COOH 2 1-环戊烯羧酸 o 1- Cvclopentenecarboxylic acid

Organic Chemistry Organic Chemistry Xiamen Xiamen University University COOH Br 1 2 3 4 5 6 3-Bromoc yclohexanecarbox ylic acid 3-溴环己烷羧酸 1-环戊烯羧酸 COOH 1 2 4 3 5 1-C yclo pentenecarbox ylic acid