CHEM 231 Lecture Notes - Lecture 6: Electrophile, Carbocation, Bond Length
5 Jun 2016
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Atoms generally hybridize in a way that will give less p character: do this so they can stabilize e. Patterns: lone pair adjacent to double bond/triple bond, multiple bond, double bond adjacent to empty orbital. Essentially just more bond and charge: poor man"s resonance structure. Charges separated = bad: equivalent structures are good. The better a structure is, the bigger the contribution is: neg charge on an electroneg atom, etc, trans gives lower e than cis. Groups big enough that they physically bump into each other: trans is more stable than cis. More substituted double bonds are more stable than less substituted. When more energy is released, alkenes are more stable: bond length and strength, trans are more stable than cis. Steric interaction, more substituted alkenes are more stable. Sp2 has more s character and shorter than sp3-sp3. Tertiary > secondary > primary: primary are too unstable to invoke and are not reasonable species/intermediates.
