Ex1-p05 S06 - a similar fashion, the trans-2-propenyl...

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6. One route to solutions of carbocations which can be studied as stabilized species involves the generation of such materials in very polar solvents by the action of very powerful Lewis acids on organo halides. One such example, the generation of a solution of tert -butyl carbocations by the reaction of t-butyl chloride with antimony pentafluoride, is shown below: H 3 C C CH 3 CH 3 Cl SbF 5 S O O Cl F (solvent) ; -100 o H 3 C C CH 3 CH 3 ClSbF 5 However, when the 1-chloro-2,3-dimethyl cyclopropane isomer shown below was treated in
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Unformatted text preview: a similar fashion, the trans-2-propenyl carbocation (also shown below) was formed. Cl H H H 3 C H H 3 C SbF 5 S O O Cl F (solvent) ; -100 o ClSbF 5 Rationalize what is going on here (explain what kind of reaction is leading to the product shown, being as specific as possible), and make clear why that material forms specifically with a trans double bond. (10 points)...
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This note was uploaded on 05/03/2008 for the course CHEM 210-3 taught by Professor Trzupek during the Spring '08 term at Northwestern.

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