《有机化学》第四章烯烃和环烷烃.pptVIP

Nomenclature of the Substituted Monocycloalkanes If there is only one substituent, do not use the “1”. If there is more than one substituent, you must use all numbers, including “1”! Number around the ring in a direction to get from the first substituent to the second substituent by the shorter path. For equivalent degrees of substitution, number in a direction that follows the alphabetical sequence. A carbon with greater substitution has precedence in numbering. * 1,1-Dimethylcyclohexane * 4-Ethyl-1,1-dimethylcyclohexane * Two Ways of Naming This 1-Isopropyl-2-methylcyclohexane 1-Methyl-2-(1-methylethyl)cyclohexane * 3-Cyclobutyl-3-methylpentane * Cycloalkyl Groups * Nomenclature of Monocyclkenes 从双键碳原子开始编号 使取代基位次尽可能小 * 反式加成 第六节 烯烃的亲电加成反应历程 烯烃与溴加成 在极性分子诱导下，非极性的乙烯分子和溴分子发生极化。 溴鎓离子 * Mechanism of Bromination of an Alkene * WHAT WOULD EXPLAIN FORMATION OF ONLY THE trans PRODUCT ? ..... A BRIDGED OR CYCLIC INTERMEDIATE * CYCLIC BROMONIUM ION note size of bromine 环状溴鎓离子 * Br Br Br + BRIDGED BROMONIUM ION bridging blocks approach from this side * B r H H + B r - B r H H + B r - B r H H + B r - BRIDGED BROMONIUM ION resonance contributing structures symmetric ion - bromide ion could add to either side left or right * ENANTIOMERS symmetric intermediate + FORMATION OF ENANTIOMERS Addition could also start from the top with bromide attacking the bottom. * 2. 烯烃与HX加成 E+ = ElectrophileNu: = Nucleophile General Mechanism: The first step requires a powerful electrophile to attract the pi bond electrons, which then forms a carbocation. A nucleophile quickly adds to the carbocation to form the monosubstituted product. * 1）极化 2）碳正离子稳定性 叔（3。）仲（2 。 ）伯（1 。 ）CH3+ ?-?超共轭 3. Markovnikov Rule and Stability of Carbocation ?-p超共轭效应 * COMPETING PATHWAYS lower energy intermediate higher energy intermediate rate-determininng (slow) step rate-determining step faster slower 决速步骤 * Hyperconjugation C C H H H H H 超共轭 * CARBOCATION STABILITY HYPERCONJUGAT