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Carbocation Rearrangements
Carbocation Rearrangements

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Workshop 5
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... As mentioned in the text, diethyl ether, pentane, and 1-butanol have similar molar masses, but different physical properties. Boiling points are 35oC, 36oC, and 117oC, respectively. Their respective solubilities in water are 7.5g/100mL, insoluble, and 9g/100mL. (i) Draw structures for each of these ...
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Vinylcyclopropane rearrangement



The vinylcyclopropane rearrangement or vinylcyclopropane-cyclopentene rearrangement is a ring expansion reaction, converting a vinyl-substituted cyclopropane ring into a cyclopentene ring.Intense experimental as well as computational investigations have revealed that mechanistically, the vinylcyclopropane rearrangement can be thought of as either a diradical-mediated two-step and/or orbital-symmetry-controlled pericyclic process. The amount by which each of the two mechanisms is operative is highly dependent on the substrate.Due to its ability to form cyclopentene rings the vinylcyclopropane rearrangement has served several times as a key reaction in complex natural product synthesis.
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