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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#1. Retro-Electrochemical Reaction: A ring has been made, but the light is causing the molecule to un- cyclize. Undo the ring into all possible molecules. (2pts, no partial credit) hv
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I have a question about this problem involving mechanisms and drawing curved arrows for acids and bases. I know we need to identify the nucleophile and electrophile, but are there different types of reactions? For instance, what about Grignard reagents and other types that I might not be familiar with? Can you help me with this? I want to identify the names of the mechanisms for problems 1-14, such as Gilman reagents and others. Are they all the same? Also, could you rewrite it so I can better understand? The handwriting is pretty cluttered. Additionally, I need to label the nucleophile and electrophile, but my main concern is whether those reactions differ, like the "Brønsted-Lowry acid-base mechanism, Lewis acid-base mechanism, acid-catalyzed mechanisms, acid-catalyzed reactions, base-catalyzed reactions, nucleophilic substitution mechanisms (SN1 and SN2), elimination reactions (E1 and E2), organometallic mechanisms, and so forth."

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Organic Chemistry, Binder Ready Version

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