Multiple Bonds, Pi MOs, Delocalization. Permanganate Test Results Hexane, C 6 H 14 Hexene, C 6 H 12 Limonene Blank Pinene, C 10 H 16.

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Presentation transcript:

Multiple Bonds, Pi MOs, Delocalization

Permanganate Test Results Hexane, C 6 H 14 Hexene, C 6 H 12 Limonene Blank Pinene, C 10 H 16

Trigonal Planar Electron Group Geometry Methanal (Formaldehyde) Ethene (Ethylene) 120 o Perfect Trigonal Planar Arrangement

Bond Angles Deviate From 120 o Methanal (Formaldehyde)Ethene (Ethylene)

Two Models for Ethene

Sigma Bonding Orbital Between C Atoms in Ethene

Pi Bonding Orbital Formation at C Atoms in Ethene

The Double Bond in Ethene sigma orbital for first part of bond pi orbital for second part of bond

The Sigma Framework in Ethene

The Pi Bond in Ethene

The 5 Sigma and 1 Pi Bonding Orbitals in Ethene

Isomerism Same number, kind of atoms Different connectivity Non-superimposable mirror images Same connectivity but different spatial arrangement e.g., cis,trans Isomers Structural Isomers Stereoisomers Geometric Isomers Optical Isomers Conformational Isomers Interconvert by sigma bond rotation

Cis-Trans Isomerism Trans Cis Interconversion Requires Breaking the Pi Bond

Conformational Isomerism Interconversion Requires Only Sigma Bond Rotation Same Molecule, Just Different Rotations 1,2-dichloroethane

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