有机化学课件－烯烃制备 消去反应.pptxVIP

X; limited to industrial syntheses of ethylene,  propene, 1,3-butadiene, and styrene important economically, but rarely used in laboratory-scale syntheses;5.9Dehydration of Alcohols;(79-87%);tertiary:most reactive;5.10Regioselectivity in Alcohol Dehydration:The Zaitsev Rule;10 %;Regioselectivity; When elimination can occur in more than one direction, the principal alkene is the one formed by loss of H from the b carbon having thefewest hydrogens. ; When elimination can occur in more than one direction, the principal alkene is the one formed by loss of H from the b carbon having thefewest hydrogens. ; When elimination can occur in more than one direction, the principal alkene is the one formed by loss of H from the b carbon having thefewest hydrogens. ; When elimination can occur in more than one direction, the principal alkene is the one formed by loss of H from the b carbon having thefewest hydrogens. ;5.11Stereoselectivity in Alcohol Dehydration; A stereoselective reaction is one in which a single starting material can yield two or more stereoisomeric products, but gives one of them in greater amounts than any other.;5.12The Mechanism of Acid-CatalyzedDehydration of Alcohols; The dehydration of alcohols and the reaction of alcohols with hydrogen halides share thefollowing common features: 1) Both reactions are promoted by acids 2) The relative reactivity decreases in the order tertiary secondary primary These similarities suggest that carbocations areintermediates in the acid-catalyzed dehydration ofalcohols, just as they are in the reaction of alcoholswith hydrogen halides.;first two steps of mechanism are identical tothose for the reaction of tert-butyl alcohol withhydrogen halides ;;;;are intermediates in the acid-catalyzed dehydration of tertiary and secondary alcohols carbocations can: react with nucleophileslose a b-proton to form an alkene;avoids carbocation because primary carbocations are too unstable oxon