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Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
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Capitolo 20, Problema 18

Which of the following would you expect to be a more stable molecular orbital? Why?
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Step 1: Analyze the molecular orbital diagrams provided in the image. Diagram (I) shows a bonding molecular orbital where the lobes of the atomic orbitals overlap constructively (same phase, indicated by matching signs). Diagram (II) shows an antibonding molecular orbital where the lobes of the atomic orbitals overlap destructively (opposite phases, indicated by opposite signs).
Step 2: Recall the concept of molecular orbital stability. Bonding molecular orbitals are more stable because constructive overlap leads to increased electron density between the nuclei, which stabilizes the molecule. Antibonding molecular orbitals are less stable because destructive overlap reduces electron density between the nuclei, leading to repulsion.
Step 3: Examine the phase alignment in Diagram (I). The constructive overlap of orbitals in the bonding molecular orbital results in a lower energy state, making it more stable.
Step 4: Examine the phase alignment in Diagram (II). The destructive overlap of orbitals in the antibonding molecular orbital results in a higher energy state, making it less stable.
Step 5: Conclude that the bonding molecular orbital (Diagram I) is more stable than the antibonding molecular orbital (Diagram II) due to the constructive overlap of atomic orbitals, which increases electron density between the nuclei and lowers the energy of the system.

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Molecular Orbital Theory

Molecular Orbital Theory describes how atomic orbitals combine to form molecular orbitals, which can be occupied by electrons. These molecular orbitals can be bonding, antibonding, or non-bonding, influencing the stability of the molecule. The stability of a molecular orbital is determined by the energy levels and the overlap of the atomic orbitals involved in its formation.
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