附件2 粒大浮 教 案 2003~~2004学年第Ⅰ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 2003年09月01日
附件 2 教 案 2003~~ 2004 学年 第 I 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 2003 年 09 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):第十章.醇,酚,醚授课类型|理论课 (Alcohols, Phenols, Ethers) 授课时间第15周第47-54节 教学目标或要求:了解醇,酚,醚的分类,命名及同分异构现象。了解醇的化学性质 酚的化学性质,醚的化学性质。重点掌握醇,酚,醚的化学性质。 教学内容(包括基本内容、重点、难点) 醇,酚,醚 基本内容包括了解醇,酚,醚的分类,命名及同分异构现象。本章的重点是醇、酚、醚的重要反应 及其应用。重要反应有亲核取代反应、消除反应、重排反应等。历程主要是指SN1和SN2历程, Alcohols ethers: nomenclature Simple alcohols are named as derivatives of the parent alkane, using the suffix -ol, using the following simple rules Select the longest continuous carbon chain, conta ining the hydroxyl group, and derive the parent name by replacing the -e ending with -oL 2. Num ber the carbon chain, beginning at the end nearest to the hydroxyl group 3. Num ber the substituents and write the name, listing substituents alpha betically Some examples
有机化学（双语教学） 课程教案 授课题目（教学章节或主题）：第十章．醇，酚，醚 (Alcohols,Phenols,Ethers) 授课类型 理论课 授课时间 第 15周第 47-54节 教学目标或要求：了解醇，酚，醚的分类，命名及同分异构现象。了解醇的化学性质， 酚的化学性质，醚的化学性质。重点掌握醇，酚，醚的化学性质。 教学内容（包括基本内容、重点、难点）： 醇，酚，醚 基本内容包括了解醇，酚，醚的分类，命名及同分异构现象。本章的重点是醇、酚、醚的重要反应 及其应用。重要反应有亲核取代反应、消除反应、重排反应等。历程主要是指 SN1 和 SN2 历程， Alcohols & Ethers: Nomenclature Simple alcohols are named as derivatives of the parent alkane, using the suffix -ol, using the following simple rules: 1. Select the longest continuous carbon chain, containing the hydroxyl group, and derive the parent name by replacing the -e ending with -ol. 2. Number the carbon chain, beginning at the end nearest to the hydroxyl group. 3. Number the substituents and write the name, listing substituents alphabetically. Some Examples:
<2-13-ccloheranediol HO 4 4dimethyicycloheranol Alcohols are also known by a wide variety of common names, some of which are given below: H3C Isopropy alcohol NButyl alcohol c-methyl-2-propanon (123-propanetniol CH2OH Allylalcohol Benzyl alcohol Simple ethers are named either by identifying the two organic residues and adding the word ether, or, if other functionality is present, the ether residue is named as an alkoxy substituent, as shown below ethyl methyl ether 4-bromo-l-methoxybu Some example:
Alcohols are also known by a wide variety of common names, some of which are given below: Simple ethers are named either by identifying the two organic residues and adding the word ether, or, if other functionality is present, the ether residue is named as an alkoxy substituent, as shown below: Some Examples:
e-methyl-1-proporypropane chloro 1(2-chloroproporyh2-methyipropane Reactions of alcohols Conversion to Alkyl Chlorides by Reaction with HCl: Tertiary alcohols, or alcohols which can lose the hydroxyl group to form a stable carbocation, can undergo an S,I substitution reaction with hcl gas dissolved in ether to give the corresponding alkyl chloride. Again, the reaction is limited to alcohols that can from stable carbocations ether.0°c CH Conversion to Alkyl Bromides by Reaction with PBr. Primary and secondary alcohols react with PBr, to form an intermediate phosphite ester which undergoes S,2 attack by bromide anion to yield the alkyl bromide with inversion of configuration(the stereochemical inversion is simply a result of the displacement)
Reactions of Alcohols Conversion to Alkyl Chlorides by Reaction with HCl: Tertiary alcohols, or alcohols which can lose the hydroxyl group to form a stable carbocation, can undergo an SN1 substitution reaction with HCl gas dissolved in ether to give the corresponding alkyl chloride. Again, the reaction is limited to alcohols that can from stable carbocations. Conversion to Alkyl Bromides by Reaction with PBr3: Primary and secondary alcohols react with PBr3 to form an intermediate phosphite ester which undergoes SN2 attack by bromide anion to yield the alkyl bromide with inversion of configuration (the stereochemical inversion is simply a result of the SN2 displacement)
R ether.35°c PB -Br Displac B CH3CH CH3CH2 a phosphite ester Conversion to Alkyl Chlorides by Reaction with SoCl, Primary and secondary alcohols react with SoCl, in polar solvents (i. e, pyridine) to form an intermediate sulfite ester which undergoes S2 attack by chloride anion to yield the alkyl chloride with inversion of configuration(the stereochemical inversion is simply a result of the S,2 displacement). If the reaction is performed in a non-polar solvent such as benzene, an unusual S, i mechanism occurs involving frontside attack, and yielding retention of stereochemistry. This reaction is unusual, but is often useful if you desire to control the stereochemical course of a synthesis sOCI2 pendine Non-Polar CI/NN2Displacement SNi Displacement with Inversion with Retention a sulfite ester a sulfite este Dehydration of Tertiary Alcohols: Tertiary alcohols, or alcohols which can lose the hydroxyl group to form a stable carbocation, can undergo an acid-catalyzed El elimination reaction to form the corresponding alkene. Again, the reaction is limited to alcohols that can from stable carbocations
Conversion to Alkyl Chlorides by Reaction with SOCl2: Primary and secondary alcohols react with SOCl2 in polar solvents (i.e., pyridine) to form an intermediate sulfite ester which undergoes SN2 attack by chloride anion to yield the alkyl chloride with inversion of configuration (the stereochemical inversion is simply a result of the SN2 displacement). If the reaction is performed in a non-polar solvent such as benzene, an unusual SNi mechanism occurs involving frontside attack, and yielding retention of stereochemistry. This reaction is unusual, but is often useful if you desire to control the stereochemical course of a synthesis. Dehydration of Tertiary Alcohols: Tertiary alcohols, or alcohols which can lose the hydroxyl group to form a stable carbocation, can undergo an acid-catalyzed E1 elimination reaction to form the corresponding alkene. Again, the reaction is limited to alcohols that can from stable carbocations