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Subs%tución Electro1lica Aromá%ca (S E Ar)

Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

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Page 1: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Subs%tución  Electro1lica  Aromá%ca  (SEAr)  

Page 2: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

What  Is  Coal?  

Page 3: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 4: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 5: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Nomenclature  of  Benzene  Deriva%ves  

Page 6: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 7: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 8: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Polysubs%tuted  Deriva%ves  of  Benzene  

1.  Iden%fy  and  name  the  parent.    2.    Iden%fy  and  name  the  subs%tuents.    3.  Assign  a  locant  to  each  subs%tuent.    4.  Arrange  the  subs%tuents  alphabe%cally.  

Page 9: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 10: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Structure  of  Benzene  

A.  Kekulé  (1866)  

Page 11: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Stability  of  Benzene  

Page 12: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 13: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 14: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 15: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 16: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 17: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

The  Criteria  for  Aroma%city  

 1.  The  compound  must  contain  a  ring  comprised  of  con%nuously  overlapping  p  orbitals.    2.  The  number  of  π  electrons  in  the  ring  must  be  a  Hückel  number.  

Page 18: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Aroma%c  Heterocycles  

Page 19: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Reac%ons  at  the  Benzylic  Posi%on  

Page 20: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Electrophilic  Aroma%c  Subs%tu%on  

Page 21: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 22: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Mecanismo  general  

Page 23: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Halogena%on  

Page 24: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 25: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 26: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 27: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Sulfona%on  

Page 28: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 29: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Nitra%on  

Page 30: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 31: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 32: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Friedel-­‐CraZs  Alkyla%on  

Page 33: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 34: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 35: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 36: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

Friedel-­‐CraZs  Acyla%on  

Page 37: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 38: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)
Page 39: Subs%tución+Electro1lica+ Aromáca ( SEAr)depa.fquim.unam.mx/amyd/archivero/SEA_30683.pdf · 3H2 -208 . Node Antibonding MO Bonding MO . Six isolated p orbitals (with six electrons)

 Clemmensen  reduc%on