133羧酸.ppt
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1、12 羧酸 (重点,难点),12.1 羧酸的结构、分类、命名 12.2 羧酸的制备 12.3 羧酸的物理性质:波谱性质 12.4 羧酸的化学性质:酸性;羟基取代;羧基还原;羧酸盐脱羧;-氢的卤代;二元酸的受热反应 12.5 羟基酸的化学性质:酸性、脱水、脱羧,第十二章 羧酸及其衍生物,12.1羧酸的结构,形式上看,羧基由羰基和羟基组成。羟基氧原子的未共用电子对所占据的p轨道和羰基的键形成p-共轭。羟基氧上电子云密度有所降低,羰基碳上电子云密度有所升高。,羧 基 (carboxyl),脂肪羧酸:RCOOH 芳香羧酸:ArCOOH 饱和脂肪羧酸; 不饱和脂肪羧酸: 根据羧基数目不同:分为一元羧酸、
2、二元羧酸和多元羧酸。 肥皂:高级脂肪酸的钠盐; 动物油:饱和高级脂肪酸的甘油酯; 植物油:不饱和高级脂肪酸的甘油酯; 食用醋:2%的乙酸水溶液。,12.2 羧酸的分类和命名,12.2.1 羧酸的分类,羧 基 (carboxyl),酰基: 羧酸分子中的羧基除去羟基后的基团; 酰氧基:羧酸分子中的羧基除去氢原子后的基团。,12.2.2 羧酸的命名,甲酸,蚁酸,(甲)俗名,乙酸,醋酸,丁酸,酪酸,十八酸,硬脂酸,(乙)普通命名法, - 甲基丁酸, -甲基- -戊稀酸, -羟基戊酸, , ,羧基连在苯环上:以芳甲酸为母体,环上其他基团为取代基; 羧基连在侧链上:以脂肪酸为母体,芳基作为取代基。,3-苯
3、基丙烯酸,二元酸的主链包括两个羧基,叫某二酸。脂环羧酸常把脂环烃看作取代基:,环戊基甲酸,(丙)系统命名法,(A)脂肪族羧酸,母体:,选含羧基的最长连续碳链,不饱和羧酸选含羧基和不饱和键在内的最长连续碳链为主链.,4 3 2 1,18 12 10 9 1,5 4 3 2 1,4-溴丁酸,12-羟基-9-十八碳烯酸,2-甲基3-乙基丁二酸,(顺)-丁烯二酸,4-丁基-2,4-戊二烯酸,(B)含环羧酸,羧基与环相连:,母体为芳烃(或脂环烃)名称+甲酸.,对甲基苯甲酸,2,4-环戊二烯甲酸,反-1,2-环戊烷二甲酸,羧基与侧链相连:,母体为脂肪酸.,3-苯基丙烯酸,1,2-苯二乙酸,3-环戊基丁酸,
4、Nomenclature:,Simple carboxylic acids are named as derivatives of the parent alkane, using the suffix-oic acid 1. Select the longest continuous carbon chain, containing the carboxylic acid group, and derive the parent name by placing the -e ending with -oic acid. 2. Number the carbon chain ,beginnin
5、g at the end nearest to the carboxylic acid group. 3. Number the substituents and write the name, listing substituents alphabetically. 4. Carboxylic acid substituents attached to rings are named using the suffix -carboxylic acid.,2-ethylpentanoic acid,2-ethylpentanoic acid,3-bromo-2-ethylbutanoic ac
6、id,name as a cyclohexenecarboxylic acid,2-ethylpentanoic acid,3-bromo-2ethylpentanoic acid,2-cyclohexenecarboxylic acid,name as a benzoic acid derivative,2-ethylpentanoic acid,3-bromo-2ethylpentanoic acid,5-bromo-2-methylbenzoic acid,2-cyclohexnecarboxylic acid,12.3 羧酸的制法,12.3.1 羧酸的工业合成,一、烃的氧化,二、伯醇和
7、醛氧化,甲基酮氧化,(2)腈水解,腈水解是合成羧酸的重要方法之一.,( 1, 2),注意:,例:,丁二酸,丙二酸,Strecker反应,a-羟基酸,a-氨基酸,腈的酸催化水解机理:,腈的碱催化水解机理,是由卤代烃(1、2、3卤代烷、烯丙基卤和芳基卤)制备多一个碳原子羧酸很有效的方法。,(3)Grignard试剂与CO2作用,亲核加成反应,(4)酚酸合成Kolbe-Schmidt反应,工业上是在加热加温下,由苯酚钠和二氧化碳作用生成邻羟基苯甲酸.,Oxidation of Aromatic Side-Chains with Permaganate,The benzylic carbon must
8、 have at least one hydrogen.,Oxidation of Aromatic Side-Chains with Permaganate,The benzylic carbon must have at least one hydrogen.,Synthesis of Carboxylic Acids by Oxidation of Primary Alcohols,Primary alcohols react with Jones reagent to from carboxylic acids; 3 alcohols do not react.,。,Synthesis
9、 of Carboxylic Acids by Oxidation of Terminal Alkenes with Acidic MnO4-.,The oxidation of aldehydes by silver oxide in aqueous ammonia forms the basis for the Tollens test for aldehydes.,Metallic silver is deposited in a thin “mirror” coating.,Ketones can be oxidized to the corresponding carboxylic
10、acidby extended reaction with acidic permaganate.,hexanedioic acid,Synthesis of Carboxylic Acids by Hydrolysis of Nitriles,Strong acid and heat are generally required for this conversion.,Synthesis of Carboxylic Acids by Carboxylation of Grignard Reagents,Predict the products of the following reacti
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