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CHEM152L(7_6_09)

CHEM152L(7_6_09) - CHEM 152L Summer 2009 Stereochemistry of...

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CHEM 152L Summer 2009 7-06-09 Stereochemistry of Diels Alder Reaction –
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CHEM 152L Summer 2009 discuss the formation of endo product forming primarily over exo product (secondary orbital overlap) Addition of Hydrogen Halides and Halides to conjugated dienes – React with HCl, HBR just like alkenes as do Cl 2 and Br 2 , but give rise to two different products. + Cl 2 + Cl Cl 1, 2 addition Cl Cl 1, 4 addition + HBr + Br H H Br 1, 4 addition 1, 2 addition So in order to understand how this happens we must look at the mechanism of the reaction: Formation of allylic carbocation!
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CHEM 152L Summer 2009 Thermodynamic versus kinetic control – two factors that are important when we discuss electrophilic addition to the conjugate diene – temperature and structure of reactant. When a reaction produces more than one product, the one that is formed fastest is called the kinetic product, the one that is more stable (energetically more favorable) is called the thermodynamic product. For many organic reactions the kinetic and thermodynamic
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