ELIMINATION REACTIONS：消除反应.pptVIP

03/courses/index.html ALKYL HALIDES – ELIMINATION REACTIONS ALKYL HALIDES UNDERGO ELIMINATION OF HX WHEN TREATED WITH BASE. THE PRODUCTS ARE ALKENES. ELIMINATION REACTIONS USUALLY REQUIRE FORCING CONDITIONS, I.E. HEAT AND STRONG BASE. THE ELIMINATION REACTIONS WHICH ALKYL HALIDES UNDERGO ARE KNOWN AS I,2-ELIMINATIONS OR ? ELIMINATIONS. ALKYL HALIDES: ELIMINATION REACTIONS The elements of H-X are lost from neighboring carbon atoms and a C=C is formed. The head carbon of the alkyl halide is termed ? (“alpha”) and the carbon atom or atoms next to it are designated ? (“beta”). The halogen atom is lost from the ? carbon, and the hydrogen from one of the ? carbons. ALKYL HALIDES: ELIMINATION REACTIONS THE TWO MOST IMPORTANT MECHANISMS BY WHICH ALKYL HALIDES UNDERGO ELIMINATION REACTIONS ARE: THE E1 MECHANISM (UNIMOLECULAR); 2. THE E2 MECHANISM (BIMOLECULAR). ELIMINATION REACTIONS OF ALKYL HALIDES: THE UNIMOLECULAR MECHANISM (E1) The slow, rate determining step entails one species – the alkyl halide. The rate of the reaction = k[alkyl halide] Note the carbocation intermediate ELIMINATION REACTIONS OF ALKYL HALIDES: THE UNIMOLECULAR MECHANISM (E1) A carbocation intermediate is formed when alkyl halides undergo elimination via the E1 (unimolecular) mechanism. 3o alkyl halides are likely to lose HX via this mechanism. For t-butyl bromide in aqueous alcoholic KOH: ELIMINATION REACTIONS OF ALKYL HALIDES: THE BIMOLECULAR MECHANISM (E2) THIS IS A CONCERTED REACTION. BOND FORMATION AND BOND BREAKING TAKE PLACE SIMULTANEOUSLY. THE RATE DETERMINING STEP ENTAILS THE BASE AND THE ALKYL HALIDE. RATE = k[alkyl halide][base] THE BIMOLECULAR MECHANISM (E2)A VERY IMPORTANT FEATURE For an alkyl halide to undergo elimination via the E2 mechanism, the H and X groups must be anti to each other and be in the same plane with each other and the carbon atoms to which they are attached. THE ELEMENTS OF H-X MUST BE ANTIPERIPLANAR. OTHER