附件2 粒大浮 教 案 2003~~2004学年第Ⅱ学期 院(系、所、部)化学与环境学院有机化学研究所 教研室有机化学 课程名称有机化学(双语教学 授课对象化学教育 授课教师杨定乔 职称职务教授 教材名称 Organic Chemistry 2004年03月01日
附件 2 教 案 2003~~ 2004 学年 第 II 学期 院（系、所、部）化学与环境学院有机化学研究所 教 研 室 有机化学 课 程 名 称 有机化学(双语教学) 授 课 对 象 化学教育 授 课 教 师 杨定乔 职 称 职 务 教授 教 材 名 称 Organic Chemistry 2004 年 03 月 01 日
有机化学(双语教学)课程教案 授课题目(教学章节或主题):第十一章.醛和酮|授课类型|理论课 Aldehydes and Ketones 第1周第55-60 授课时间 教学目标或要求:了解醛和酮的分类,命名及同分异构现象。了解醛酮亲核加成反应 历程及其制备方法。重点掌握亲核加成反应的反应历程。 教学内容(包括基本内容、重点、难点) 醛、酮 本章的重点是醛、酮的重要反应及其应用和有关反应机理。重要反应有亲核加成反应 缩合反应、α-H取代反应和氧化还原反应等。反应机理主要指亲核加成机理、羟醛缩 合机理等。难点是对结构与性质的关系、影响醛、酮亲核加成反应的因素和反应的立 体选择性的认识和理解。 aldehydes Ketones: Nomenclature Simple aldehydes and ketones are named using the standard rules of nomenclature which we have used in the past with the following specific changes 1. Aldehydes are named by replacing the term inal -e of the parent alkane with the suffix -al; the suffIx for ketone Ethanal (Acetaldehyde) 2-methylpropanal 2-propanone(Acetone) 2-methyl-2-butanone
有机化学(双语教学) 课程教案 授课题目（教学章节或主题）：第十一章．醛和酮 （Aldehydes and Ketones） 授课类型 理论课 授课时间 第 1 周第 55-60 节 教学目标或要求：了解醛和酮的分类，命名及同分异构现象。了解醛酮亲核加成反应 历程及其制备方法。重点掌握亲核加成反应的反应历程。 教学内容（包括基本内容、重点、难点）： 醛、酮 本章的重点是醛、酮的重要反应及其应用和有关反应机理。重要反应有亲核加成反应、 缩合反应、α-H 取代反应和氧化还原反应等。反应机理主要指亲核加成机理、羟醛缩 合机理等。难点是对结构与性质的关系、影响醛、酮亲核加成反应的因素和反应的立 体选择性的认识和理解。 Aldehydes & Ketones: Nomenclature Simple aldehydes and ketones are named using the standard rules of nomenclature which we have used in the past with the following specific changes: 1. Aldehydes are named by replacing the terminal -e of the parent alkane with the suffix -al; the suffix for ketones is -one
2. The parent chain selected must conta in the carbonyl gro 3. Number the carbon chain, beginning at the end nearest to the carbonyl group 4. Number the substituents and write the name, listing substituents alpha betically 3-cyclohexenone O? 3-nitrobenzaldehyde 2-hexan 4-hexen-2-one When an aldehyde is a substituent on a ring, it is referred to as a- carbaldehyde group Cyclohexanecarbaldehyde Benzenecarbaldehyde ( Benzaldehyde 6. When the-COR group becomes a substituent on another chain, it is referred to as an acyl group and the name is formed using the suffix -yl Acetyl 7. When the carbonyl group becomes a substituent on another chain, it is referred to as an oxo group 5-oxohexanal
2. The parent chain selected must contain the carbonyl group. 3. Number the carbon chain, beginning at the end nearest to the carbonyl group. 4. Number the substituents and write the name, listing substituents alphabetically. 5. When an aldehyde is a substituent on a ring, it is referred to as a -carbaldehyde group. 6. When the -COR group becomes a substituent on another chain, it is referred to as an acyl group and the name is formed using the suffix -yl. 7. When the carbonyl group becomes a substituent on another chain, it is referred to as an oxo group
Some examples 1-phenyr2-propanone czw3-methyicycloheranecar aldehyde pentanediol 3ethyl-4-pentenal Reactions of aldehydes Ketones The Grignard Reaction: The reaction of an alkyl, aryl or vinyl halide with magnesium metal in ether solvent, produces an organometallic complex of uncertain structure, but which behaves as if it has the structure r-Mg-X and is commonly referred to as a Grignard Reagent. ether R→x+Mg R-Mgx R=1°2°,or3°akyl, aryl or vinyl X=C1. Br or I R-MoX The R" group in this complex (alkyl, aryl or vinyl), acts as if it was a stabilized carbanion and Grignard reagents react with water and other compounds containing acidic hydrogens to give hydrocarbons (just as would be expected for a well-behaved, highly basic carbanion). In the absence of acidic hydrogens, the Grignard reagent can function as a powerful nucleophile, and is most often used in addition reactions involving carbony l compounds, as shown above. The product of these addition reactions is typically a secondary or tertiary alcohol (primary alcohols can be formed by reaction with formaldehyde), as shown in the examples below; in these the carbonyl and halide portions of the molecules have been colored blue and red, respectively, to assist in understanding the component parts of the final product
Some Examples: Reactions of Aldehydes & Ketones The Grignard Reaction: The reaction of an alkyl, aryl or vinyl halide with magnesium metal in ether solvent, produces an organometallic complex of uncertain structure, but which behaves as if it has the structure R-Mg-X and is commonly referred to as a Grignard Reagent. The "R" group in this complex (alkyl, aryl or vinyl), acts as if it was a stabilized carbanion and Grignard reagents react with water and other compounds containing acidic hydrogens to give hydrocarbons (just as would be expected for a well-behaved, highly basic carbanion). In the absence of acidic hydrogens, the Grignard reagent can function as a powerful nucleophile, and is most often used in addition reactions involving carbonyl compounds, as shown above. The product of these addition reactions is typically a secondary or tertiary alcohol (primary alcohols can be formed by reaction with formaldehyde), as shown in the examples below; in these the carbonyl and halide portions of the molecules have been colored blue and red, respectively, to assist in understanding the component parts of the final products
1. Melete Hgo -Br Grether 2.H3O Hydration of aldehydes Ketones The hydration of carbony l compounds is an equilibrium process and the extent of that equilibrium generally paralle ls the reactivity of the parent aldehyde or ketone towards nucleophilic substitution aldehydes are more reactive than ketones and are more highly hydrated at quilibrium. CH3 H H H2O Formation of Cyanohydrins: The reaction of carbonyl compounds with HCN is an equilibrium process and, again, the extent of that equilibrium generally parallels the reactivity of the parent aldehyde or ketone towards nucleophilic substitution
Hydration of Aldehydes & Ketones: The hydration of carbonyl compounds is an equilibrium process and the extent of that equilibrium generally parallels the reactivity of the parent aldehyde or ketone towards nucleophilic substitution; aldehydes are more reactive than ketones and are more highly hydrated at equilibrium. Formation of Cyanohydrins: The reaction of carbonyl compounds with HCN is an equilibrium process and, again, the extent of that equilibrium generally parallels the reactivity of the parent aldehyde or ketone towards nucleophilic substitution