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Organic Chemistry Main Menu Lecture 1: Introduction to Molecular Orbitals Lecture 10: Intermolecular Forces and Intro to Reactivity Lecture 11: Alkenes as Nucleophiles I Lectures 12 and 13: Alkenes II & III Lecture 14: Benzenes as Nucleophiles I Lecture 15 objectives and skills Lecture 2: Molecular Orbitals in Organic Structures Lecture 3: Molecular Orbitals and Resonance Lecture 4: Molecular Orbitals and Aromaticity Lecture 5: Nomenclature and IR Spectroscopy Lecture 6: Stereochemistry I Lecture 7: Stereochemistry II Lecture 8: Newman and Fisher Projections Lecture 9: Conformations and Cyclohexane Rings

prob e3.4 solution

35992

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SOLUTION E3.4
The alkene (2-butene) has no conjugation, so largest HOMO-LUMO gab and smallest l_max. The alkene anion is part of a conjugated system with three π-MOs, making the HOMO-LUMO gap smaller than in the isolated alkene (larger l_max). The conjugated aldehyde has the largest l_max due to the largest amount of conjugation in the system (four π-MOs).