0243Pb46an-09.cwk (WP)

0243Pb46an-09.cwk (WP) - S N 2 OH Neither the S N 2 nor the...

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Answers to Problem 46, Chemistry 0243 - 2009 Two of these bromides ( 2 and 4 ) ionize to give the same resonance-stabilized carbocation. Reaction will be at the three different carbons sharing the positive charge, and three different alcohols will result. Br Br 2 4 H 2 O OH OH OH Another, 3 , will slowly react through the S N 2 mechanism to give another alcohol. Br 3 H 2 O
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Unformatted text preview: S N 2 OH Neither the S N 2 nor the S N 1 reaction will take place at an sp 2 carbon, so bromide 1 does not react. For the pentadienyl cation, Ψ 3 is the LUMO, as there are only four electrons: Thus, addition of the nucleophile water through a filled nonbonding HOMO, can take place at carbons 1, 3, and 5, but not at 2 or 4....
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Fall '10 term at NYU.

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