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Nucleophilic Substitution A fundamental class of substitution
reaction in which an "electron rich" nucleophile selectively bonds
with or attacks the positive or partially positive charge of an
atom attached to a group or atom called the leaving
group;substitution reactionnucleophileleaving group the positive or
partially positive atom is referred to as an
electrophile.electrophile
Slide 5
Nucleophilic acyl substitution Upon attack of the nucleophile
at the carbonyl group, a tetrahedral intermediate is formed with
the nucleophile, the leaving group and the oxygen anion attached to
the central carbon atom. The alkoxy group can now revert back to
the carbonyl group and at the same time expel the leaving
group.alkoxycarbonylleaving group
Slide 6
Homo:MO28 Energy: -10.89670ev Lumo:MO29 Energy: 5.31218 ev
Slide 7
Homo: MO 46 Energy: -11.52918ev Lumo:MO47 Energy:
2.89761ev
Slide 8
Energy Gap E(LUMO) -E (HOMO) = 2.89761ev-(-10.89670ev)
=13.79431ev
Slide 9
Distanc e: 4.0 Distance: 3.5
Slide 10
Distanc e: 3.0 Distance: 2.5
Slide 11
Distance: 2.0 Distance: 1.8
Slide 12
Distance: 1.6 Distance: 1.4
Slide 13
Distance: 1.2 Distance: 1.0
Slide 14
Slide 15
Product
Slide 16
Homo: MO 56 Energy: -11.16780ev Lumo: MO57 Energy:
2.76860ev
Slide 17
Conclusion
Slide 18
Energy Gap E(LUMO) -E (HOMO) = 2.89761ev-(-10.89670ev)
=13.79431ev