Portmess Homework Q&S 110

Portmess Homework Q&S 110 - 104 STRUCTURE AND...

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( d ) Dehydrobromination of 2-bromo-2-methylpentane can involve one of the hydrogens of either a methyl group (C-1) or a methylene group (C-3). Neither alkene is capable of existing in stereoisomeric forms, and so these two are the only products of E2 elimination. ( e ) 2-Bromo-3-methylpentane can undergo dehydrohalogenation by loss of a proton from either C-1 or C-3. Loss of a proton from C-1 gives 3-methyl-1-pentene. Loss of a proton from C-3 gives a mixture of ( E )- and ( Z )-3-methyl-2-pentene. ( f ) Three alkenes are possible from 3-bromo-2-methylpentane. Loss of the C-2 proton gives 2-methyl-2-pentene. Abstraction of a proton from C-4 can yield either ( E )- or ( Z )-4-methyl-2-pentene. ( g ) Proton abstraction from the C-3 methyl group of 3-bromo-3-methylpentane yields 2-ethyl- 1-butene. E2 2-Ethyl-1-butene 3-Bromo-3-methylpentane CH 3 CH 2 CCH 2 CH 3 Br CH
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