CHM 2120 Lecture Notes - Lecture 15: Elimination Reaction, Protic Solvent, Leaving Group

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4 Dec 2014
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Notes to accompany blackboard video. E2: e = elimina?on, 2 = bimolecular rate- determining step, rate = k[electrophile][base] E2 summary: carbon: 1 , 2 , or 3 , leaving group: good (weak base, base: strong, solvent: Size of base a ects regiochemical outcome. Polar, apro?c is best. Polar, pro?c works leaving group is required: stereochemistry: an?periplanar arrangement of the proton and, regiochemistry: provided the stereochemical requirements are met: Bulky, strong bases least subs?tuted alkene (hofman product) Leaving group must be good : good enough: Cl- : not good enough (i. e. , no e2 reac?on) Pkah >10 (approximate: e. g. , naoh. Small, strong bases: e. g. , naoh, e. g. , nah. Bulky, strong bases: e. g. , dbu (1,8- diazabicyclo[5. 4. 0]undec- 7- ene, h nig"s base (diisopropylethylamine) Stereochemistry: the h and lg must be an?periplanar. This will be discussed in class. Regiochemistry: as long as the stereochemical requirements have been met: Small, strong bases most subs?tuted alkene (zaitsev product)

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