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):第二章.单烯烃授课类型|理论课 ( Alkenes 授课时间|第3周第6-12节 教学目标或要求∶了解单烯烃的结构理论以及烯烃的化学性质。掌握马氏规则和亲电 加成理论。 Alkene nomenclature Alkenes represent one of the most common functional groups in organic chemistry. An alkene contains only carbon and hydrogen (a hydrocarbon) and contains at least double bond (termed an unsaturated hydrocarbon. Alkenes have the general formula C,H, thus, an alkene with 10 carbons (n=10) will have 2(10)=20 hydrogens, or the molecular formula C,Ha each double bond therefore contributes one The root, or parent name for an unbranched alkene is taken directly from the number of carbons in the chain according to a scheme of nomenclature established by the International Union of Pure and Applied Chemistry(IUPAc), as described previously for alkanes To name alkenes 1. Find the longest chain containing the alkene The IUPAC name for an alkene is constructed of two parts: 1)a prefix(meth. prop., etc.) which indicates the number of carb parent, chain of the molecule, and 2)the suffix.. ene to indicate that the molecule is an alkane For branched-chain alkanes, the name of the parent hydrocarbon is taken from the longest continuous chain of carbon atoms containing the double bond
有机化学(双语教学) 课程教案 授课题目（教学章节或主题）：第二章．单烯烃 （Alkenes） 授课类型 理论课 授课时间 第 3 周第 6-12 节 教学目标或要求：了解单烯烃的结构理论以及烯烃的化学性质。掌握马氏规则和亲电 加成理论。 Alkene Nomenclature Alkenes represent one of the most common functional groups in organic chemistry. An alkene contains only carbon and hydrogen (a hydrocarbon) and contains at least double bond (termed an unsaturated hydrocarbon. Alkenes have the general formula CnH2 n, thus, an alkene with 10 carbons (n = 10) will have 2(10) = 20 hydrogens, or the molecular formula C1 0H2 0; each double bond therefore contributes one degree of unsaturation. The root, or parent name for an unbranched alkene is taken directly from the number of carbons in the chain according to a scheme of nomenclature established by the International Union of Pure and Applied Chemistry (IUPAC), as described previously for alkanes. To name alkenes: 1. Find the longest chain containing the alkene The IUPAC name for an alkene is constructed of two parts: 1) a prefix (meth... eth... prop..., etc.) which indicates the number of carbons in the main, or parent, chain of the molecule, and 2) the suffix ...ene to indicate that the molecule is an alkane. For branched-chain alkanes, the name of the parent hydrocarbon is taken from the longest continuous chain of carbon atoms containing the double bond
2-ethyl-l-pentene 2. Number the chain, giving the double bond the lowest possible number. Numbering of the carbons in the parent chain is always done in the direction that gives the lowest number to the double bond, or, the lowest number at the first point of difference. If there are different substituents at equivalent positions on the chain, the substituent of lower alphabetical order is given the lowest number If the same substi tuent occurs more than once in a molecule, the number of each carbon of the parent chain where the substituent occurs is given and a multiplier is used to indicate the total number of identical substi tuents: i. e dimethyl.. trimethyl.. tetraethy l. the substituents are arranged in alphabetical order, without regard for multipliers 6, 6-dimethyl-3-heptene 3. For cycloalkenes, begin numbering at the double bo nd and proceed through the double bond in the direction to generate the lowest number at the first point of difference. One of the most common mistakes in naming cycloalkenes is to generate the lowest number sequence around the ring, disregarding this rule. Once again, the numbering must begin at the double bond and proceed through the bond in the direction to generate the lowest number sequence. 1 4-cyclohexadiene 3,3, 6-trimethylcyclohexene 4, 6, 6-trimethylcyclooctene 4. Assign stereochemistry using the E-z designation Historically, alkenes have been named using cis- and trans- to represent stereochemistry around the double bond; cis- for compounds where the main substituents are on the same side of the double bond, and trans- when they are on opposite sides. This system clearly breaks down, however, in more complex molecules where decisions concerning the main substituents" are not easily made, and the e-z system provides a set of rules to aid in these decisions
2. Number the chain, giving the double bond the lowest possible number. Numbering of the carbons in the parent chain is always done in the direction that gives the lowest number to the double bond, or, the lowest number at the first point of difference. If there are different substituents at equivalent positions on the chain, the substituent of lower alphabetical order is given the lowest number. If the same substituent occurs more than once in a molecule, the number of each carbon of the parent chain where the substituent occurs is given and a multiplier is used to indicate the total number of identical substituents; i.e., dimethyl... trimethyl... tetraethyl..., etc. In constructing the name, substituents are arranged in alphabetical order, without regard for multipliers. 3. For cycloalkenes, begin numbering at the double bond and proceed through the double bond in the direction to generate the lowest number at the first point of difference. One of the most common mistakes in naming cycloalkenes is to generate the lowest number sequence around the ring, disregarding this rule. Once again, the numbering must begin at the double bond and proceed through the bond in the direction to generate the lowest number sequence. 4. Assign stereochemistry using the E-Z designation Historically, alkenes have been named using cis- and trans- to represent stereochemistry around the double bond; cis- for compounds where the "main substituents" are on the same side of the double bond, and trans- when they are on opposite sides. This system clearly breaks down, however, in more complex molecules where decisions concerning the "main substituents" are not easily made, and the E-Z system provides a set of rules to aid in these decisions
You will see later that these same rules are used in assigning priorities for determining absolute configuration in chiral molecules H "A-2-butene The rules for assigning e-z designations are as follows: 1. rank atoms directly attached to the double bond according to their atomic 2. if there is a tie at any substituent, look at the second, third, etc until a difference is found 3. multiple bonds count as multiples of that same atom 4. if the highest priority groups are on the same side of the double bond, the molecule is Z; if the highest priority groups are on opposite sides the molecule is E (atomic numbers shown in red) H Z-2-b1000-2-butene Z-3-bromomethyl-4-methyl-2-pentene E- 3-methyl-1, 3-pentadiene H H2BrC, cH 6C 6 CHa CCM HHH HHE ,,,M, (these indicate the atoms attached to each of the atoms directly attached to the alkene) Alkenes: Addition oxidation reactions HBr
You will see later that these same rules are used in assigning priorities for determining absolute configuration in chiral molecules. The rules for assigning E-Z designations are as follows: 1. rank atoms directly attached to the double bond according to their atomic number 2. if there is a "tie" at any substituent, look at the second, third, etc., until a difference is found 3. multiple bonds count as multiples of that same atom 4. if the highest priority groups are on the same side of the double bond, the molecule is Z; if the highest priority groups are on opposite sides, the molecule is E Alkenes: Addition & Oxidation Reactions
H"H。O AC)2,H NaBH4 1. BH. THF 2, H2O2, Ho 1.0804 2. NaHSO3, H2o KMno4, HO /H2O CHCL KOH CH2I2, Zn(Cu), ether H H