Organic Chemistry, Binder Ready Version
Organic Chemistry, Binder Ready Version
2nd Edition
ISBN: 9781118454312
Author: David R. Klein
Publisher: WILEY
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Chapter 17.8, Problem 20CC
Interpretation Introduction

Interpretation:

The given [4+4] cycloaddition process should be explained with the use of MO theory whether it occurs through thermal or photochemical pathway.

Concept introduction:

According to MO theory,

  • In a molecule, the atomic orbitals of atoms constituted in the molecule are combined to produce new orbitals are called Molecular Orbitals.
  • The numbers of MO’s are equals to the number of atomic orbitals are combined in such a way that the linear combination of similar atomic orbitals to form equal numbers of bonding and anti-bonding MO’s.
  • The bonding MO’s are lower in energy than the anti-bonding MO’s.
  • HOMO is the highest energized occupied orbital in the MO’s.
  • LUMO is the lowest energized orbital in the MO’s.

Frontier orbital theory says,

  • In a cycloaddition reaction, the electron cloud flows from HOMO of the one molecule to LUMO of the other molecule.

According to conservation of orbital symmetry,

  • The phases of MO’s (HOMO & LUMO) of reactants must be symmetric in order to reaction occur.
  • The thermal pathway of cycloaddition reaction occurs in the ground state of 1,3-butadiene.
  • The photochemical pathway of cycloaddition reaction occurs in the excited state of 1,3-butadiene.

To explain: the given [4+4] cycloaddition process with the use of MO theory whether it occurs through thermal or photochemical pathway.

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