Lecture 232014.pdf

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CHEM 2332H
Christopher J.Douglas

Lecture 232014Monday February 3 2014859 AMTodayElectrocyclic reactionsIntro to Sigmatropic RearrangementsCope Oxycope rearrangementsUVVis SpectroscopyColored Organic CompoundsElectrocyclic conrotatorydisrotatoryHave continuous pi systemRxn taking placeend of pi systemDisrotatory defines rotationends of pi system as like same torque sense conrotatory or unlike opposite torque disrotatoryThermalPhotochemicalelectrons4ncondiselectrons4n2disconheatlight hvfocus hereOrbital Symmetry4nLookHOMOWant to rotate the double bonds have the in and out groups be up and down so that the pi bonds overlap and then can make a sigma bond with itselfNeed to rotate both bonds in the same direction but can arbitrarily choose which direction to rotateIn above example since 2 torques line up rotate in same directionconrotatoryThe in and out groups are trans to each other can see by trying to rotate hands with pinky and thumb as in and out groups respectivelyThis molecule is chiral get its enantiomer when you flip itSince the beginning molecule is achiral and then chiral produces racemic mixtureex 4n2 caseWant to look at the HOMO bc thats where the electrons areLUMO doesnt have any electrons in there22 and 42 switch in photochemical so does this oneCan make phases anyway as long as you switchnodesRotate the same way so thatpi orbitals line up again opposite torques Ochem Page 1
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