10-第十章 醇和醚课件.ppt

有机化学 李晓川 When more than one elimination product can be formed, the major product is the more substituted alkene—the one obtained by removing a proton from the –carbon that is bonded to the fewest hydrogens. (Recall Zaitsev’s rule) 当不止一个消除产物生成时，主要产物是取代基较多的烯烃—通过夺去含有较少氢原子的β碳上质子。 we saw that an alkene is hydrated (adds water) in the presence of an acid catalyst, thereby forming an alcohol. The hydration of an alkene is the reverse of the acid-catalyzed dehydration of an alcohol. 我们知道烯烃在酸催化下可以水合，因此生成醇。烯烃水合是醇在酸催化下脱水反应的逆反应。 To prevent the alkene formed in the dehydration reaction from adding water and reforming the alcohol, the alkene can be removed by distillation as it is formed, because it has a much lower boiling point than the alcohol. Removing a product displaces the reaction to the right. (See Le Chatelier’s principle) 为了防止脱水反应生成的烯烃再水合生成醇，烯可以边反应边蒸馏，因为烯烃的沸点比醇低。除去反应体系中的产物可以使反应向右进行。 If a chemical system at equilibrium experiences a change in concentration, temperature, volume, or partial pressure, then the equilibrium shifts to counteract the imposed change and a new equilibrium is established. 把平衡状态的某一因素加以改变之后，将使平衡状态向抵消原来因素改变的效果的方向移动。 Henri Louis Le Chatelier (8 October 1850 - 17 September 1936) was an influential French chemist of the late 19th and early 20th centuries. 勒·夏特列原理 发明了氧炔焰发生器，迄今还用于金属的切割和焊接。 Because the rate-determining step in the dehydration of a secondary or a tertiary alcohol is formation of a carbocation intermediate, the rate of dehydration parallels the ease with which the carbocation is formed. Tertiary alcohols are the easiest to dehydrate because tertiary carbocations are more stable and therefore are easier to form than secondary and primary carbocations. In order to undergo dehydration, tertiary alcohols must be heated to about 50 ℃ in 5% H2SO4 secondary alcohols must be heated to about 100 ℃ in 75% H2SO4 and primary alcohols can be dehydrated only under extreme conditions (170 ℃ in 95% H2SO4) and by a different mechanism because primary car