CHEM 2OA3 Lecture Notes - Hydride, Alkyl, Epoxide

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The hydrogen doesn"t jump, it"s a smooth transfer (orbitals have to line up correctly) Won"t have to give a product and have to anticipate a hydride shift occurring: we will have to be able to recognize it he gives us the reactant, condition, and the product. Ch3-c(ch3)2-c(oh)(h)-ch3 ---hbr : expected: ch3-c(ch3)2-c(br)(h)-ch3, actual: ch3-c(ch3)(br)-c(ch3)(h)-ch3, the oh got an h+ and broke off as h2o, leaving the carbocation (c-3). The ch3 connected to the carbon-2 shifts to the carbon-3, leaving carbon-2 as a carbocation. Almost any alkyl group can undergo this shift. Ether: c-o-c (r-o-r) (partial positive on the carbons, partial negative on oxygen) Ether chemistry: stable c-o bond (stable, not very reactive, sometimes use it as solvents because it doesn"t react much, pretty much only react with strong acids. Ethers can also be cyclic: make a cyclic carbon ring, replace one carbon with an oxygen. Cyclopentane with a carbon replaced with an oxygen = tetrahydrofuran.

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