《有机化学精品教学》（汕头大学）Chap 8 Ethers，Epoxides（2012b）.pptVIP

Opening of unsymmetrical epoxides in acid is a SN1 reaction. Epoxides react with proton to form a stable carbocation, then react with nucleophiles. Opening of unsymmetrical epoxides in base is a SN2 reaction. Nucleophiles will attack at sterically less hindered end of the epoxide. sulfoxide sulfone Thioethers R－S－R Oxidation of Thioethers ● Unlike ethers, sulfides can easily be oxidized to sulfoxides, usually with hydrogen peroxide, H2O2. Further or more vigorous oxidation gives sulfones. Ca(ClO)2 : calcium hypochloride (bleaching powder) Mustard gas is lethal in a few minutes at 0.02-0.05% concentration. The mustard can penetrate the rubber in use in gas masks. The toxicity will decrease remarkably if thioethers be oxidated to form sulfoxide or sulfone. Exercises page 149. 1.(2)(3)(5)(6) 3.(2)(3) 5. 6.(2)(4) * Ethers ( R O R’) Chap 8 Ethers，Epoxides simple ethers (symmetrical ethers) mixed ethers (unsymmetrical ethers) Ⅰ. Nomenclature Naming ethers is simple. The two groups joined by oxygen are named in alphabetical order and the word “ether” appended. dimethyl ether diethyl ether or ether Ether, anaesthetic, 1846年 Nitrous, anaesthetic 笑气是一氧化二氮。是一种氧化剂，化学式N2O，在一定条件下能支持燃烧。在室温下稳定，有轻微麻醉作用，并能致人发笑。笑气是人类最早应用于医疗的麻醉剂之一，是一种无色气体，人吸入后狂笑不住，有麻醉作用。其麻醉作用于1799年由英国化学家汉弗莱·戴维发现。该气体早期被用于牙科手术的麻醉。因全麻效果差，目前常与氟烷、甲氧氟烷、乙醚或静脉全麻药合用。现已少用。氧化亚氮(N2O)用于麻醉,对呼吸道无刺激,对心、肺、肝、肾等重要脏器功能无损害。在体内不经任何生物转化或降解,绝大部分仍以原药随呼气排出体外,仅小量由皮肤蒸发,无蓄积作用。吸入体内只需要30s～40s 即产生镇痛作用,镇痛作用强而麻醉作用弱,受术者处于清醒状态(而不是麻醉状态) ,避免了全身麻醉并发症,术后恢复快 ethyl methyl ether ethyl phenyl ether Phenoxy C6H5O– Phenyl C6H5– tert-Butoxy (CH3)3CO– tert-Butyl (CH3)3C– Isopropoxy (CH3)2CHO– Isopropyl (CH3)2CH– Ethoxy CH3CH2O– Ethyl CH3CH2– Methoxy CH3O– Methyl CH3– Name Alkoxy Group Name Alkyl Group 2-methoxypentane 2-ethoxy-1-phenylbutane 4-ethoxy-2-methyl-1-hexene 3-isopropoxy-1-butanol ethylene oxide propene oxide or 1,2-epoxypropane or 2-methyl ethylene oxide or oxirane