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Portmess Homework Q&S 115

Portmess Homework Q&S 115 - 109 STRUCTURE AND...

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( d ) The bromine substituent may be at either C-2 or C-3. 5.34 ( a ) The isomeric alkyl bromides having the molecular formula C 5 H 11 Br are: ( b ) The order of reactivity toward E1 elimination parallels carbocation stability and is tertiary secondary primary. The tertiary bromide 2-bromo-2-methylbutane will undergo E1 elimi- nation at the fastest rate. ( c ) 1-Bromo-2,2-dimethylpropane has no hydrogens on the carbon and so cannot form an alkene by an E2 process. The only available pathway is E1 with rearrangement. ( d ) Only the primary bromides will give a single alkene on E2 elimination. base E2 1-Bromo-3-methylbutane 3-Methyl-1-butene CH 3 CHCH 2 CH 2 Br CH 3 CH 3 CHCH CH 2 CH 3 base E2 1-Bromo-2-methylbutane 2-Methyl-1-butene CH 3 CH 2 CHCH 2 Br CH 3 CH 3 CH 2 C CH 2 CH 3 CH 3 CH 2 CH 2 CH CH 3 CH 2 CH 2 CH 2 CH 2 Br
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