Pericyclic Reaction · worked at the University of Kiel and discovered this reaction in 1928. They...
Transcript of Pericyclic Reaction · worked at the University of Kiel and discovered this reaction in 1928. They...
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Pericyclic Reaction
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ψ1
HOMO
ψ5
LUMO
ψ2
ψ3
ψ4
ψ1
ψ5
ψ2
ψ3
ψ4
No of conjugated p orbitals (np) = 5No of π-molecular orbitals = 5
npis odd, nBMO = (np-1)/2 = 2nAMO = (np-1)/2 = 2nNMO = 1
Pericyclic Reactions: π-Molecular Orbital
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Indicate the following as BMO, AMO or NBO
Pericyclic Reactions: π-Molecular Orbital
I II
IVIII
Order of energy: I>II>III>IV
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Pericyclic Reactions: Reactivity
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Based on FMO theory, predict whether the following reaction is feasible or not
Pericyclic Reactions: Reactivity
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Based on FMO theory, predict whether the following reaction is feasible or not
Pericyclic Reactions: Reactivity
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worked at the University of Kiel anddiscovered this reaction in 1928. Theywon the Nobel Prize in 1950.
Otto Diels (1876–1954) Kurt Alder (1902–58)
Diene Dienophile
Pericyclic Reactions: Selectivity of Diels-Alder Reaction
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Geometry of dienophile retained
Pericyclic Reactions: Selectivity in Diels-Alder Reaction
HOMO (ψ2) LUMO (ψ2)
Only Cis-product
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Geometry of dienophile is retained: cis-alkene give cis-product and trans-alkene gives trans-product
Pericyclic Reactions: Selectivity in Diels-Alder Reaction
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Pericyclic Reactions: Selectivity in Diels-Alder Reaction
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Why HOMO of diene interact with the LUMO of Dienophile?
Pericyclic Reactions: Selectivity of Diels-Alder Reaction
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Looking forward
Pericyclic Reaction:Reactivity and Selectivity of electrocyclic reactionPericyclic Reactions in Biological Systems
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