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Subs%tución vs. eliminación

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Page 1: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Subs%tución  vs.  eliminación  

Page 2: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Reacciones  de  eliminación  

•  Cuando  dos  grupos  en  átomos  adyacentes  se  pierden,  se  forma  un  enlace  doble  o  triple  

Page 3: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Reacciones  de  eliminación  

E1  

E2  

Page 4: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Subs%tución  vs.  eliminación  

•  Nucleófilos  que  son  bases  fuertes,  favorecen  eliminación  sobre  subs%tución  

•  Nucleofilos  (o  bases)  voluminosos  favorecen  eliminación  sobre  subs%tución  

•  Altas  temperaturas  favorecen  eliminación  sobre  subs%tucion.    

Page 5: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

SN1/E1  

Page 6: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene
Page 7: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Regla  de  Zaitsev  

Page 8: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Regla  de  Zaitsev  

Page 9: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Problema:  mecanismo  de  reacción?  

Page 10: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

La  reacción  E2  

Page 11: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene
Page 12: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene
Page 13: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Regioselec%vidad  en  la  reacción  E2  

Page 14: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene
Page 15: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Regla  de  Zaitsev  

Page 16: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Reac%vidades  rela%vas  en  una  reacción  E2    

Page 17: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene
Page 18: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Subs%tución  vs.  eliminación  

•  Nucleófilos  que  son  bases  fuertes,  favorecen  eliminación  sobre  subs%tución  

•  Nucleofilos  (o  bases)  voluminosos  favorecen  eliminación  sobre  subs%tución  

•  Altas  temperaturas  favorecen  eliminación  sobre  subs%tucion.    

Page 19: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene
Page 20: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

Resumen  SN1,  SN2,  E1  y  E2  

Page 21: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene
Page 22: Subs%tución+vs.+eliminación+depa.fquim.unam.mx/amyd/archivero/ELIMINACION_24833.pdfCH3C—CCH3 2,3-dimethyl- 2-butene More substituted product 79% CH3CHC=CH2 2,3-dimethyl- 1 -butene

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