Portmess Homework Q&S 102

Portmess Homework Q&S 102 - 96 STRUCTURE AND...

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This secondary carbocation can rearrange to a more stable tertiary carbocation by a methyl group shift. Loss of a proton from the 1,2-dimethylcyclohexyl cation intermediate yields 1,2-dimethylcyclo- hexene. 5.17 ( b ) All the hydrogens of tert -butyl chloride are equivalent. Loss of any of these hydrogens along with the chlorine substituent yields 2-methylpropene as the only alkene. ( c ) All the b hydrogens of 3-bromo-3-ethylpentane are equivalent, so that b -elimination can give only 3-ethyl-2-pentene. ( d ) There are two possible modes of b -elimination from 2-bromo-3-methylbutane. Elimination in one direction provides 3-methyl-1-butene; elimination in the other gives 2-methyl-2-butene. The major product is the more highly substituted alkene, 2-methyl-2-butene. It is the more stable alkene and corresponds to removal of a hydrogen from the carbon that has the fewer hydrogens. ( e ) Regioselectivity is not an issue here, because 3-methyl-1-butene is the only alkene that can be
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