Dolbier HW Solutions 695

Dolbier HW - 789 APPENDIX A Step 2 Rearrangement by methyl migration to form a more stable tertiary carbocation CH3 CH3C CH3 CHCH3 CH3C CH3 CHCH3

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APPENDIX A 789 Step 2: Rearrangement by methyl migration to form a more stable tertiary carbocation Step 3: Capture of the carbocation by water, followed by deprotonation A-5. ( a ) S N 1, unimolecular substitution; rate 5 k [(CH 3 ) 3 CBr] ( b ) S N 2, bimolecular substitution; rate 5 k [C 6 H 11 Cl][NaN 3 ] A-6. ( a ) Sodium iodide is soluble in acetone, whereas the byproduct of the reaction, sodium bromide, is not. According to Le Chatelier s principle, the reaction will shift in the direction that will replace the component removed from solution, in this case toward product. ( b ) Protic solvents such as water form hydrogen bonds to anionic nucleophiles, thus stabi-
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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