0243Pb66an-09.cwk (WP)

0243Pb66an-09.cwk (WP) - Now what? You know from the answer...

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Answers to Problem 66, Chemistry 0243 - 2009 (a) Protonation gives the secondary (not primary) carbocation which then adds to the other double bond, again to give the more stable secondary carbocation. There are two different ptotons that can be lost; one gives 2 ; the other 3 . H Hb Ha + = + + H 3 O + H 2 O 2 (loss of H b ) 3 (loss of H a ) (b) CH 3 OH OH H 2 SO 4 CH 3 OH 2 OH CH 3 OH Note formation of the tertiary carbocation. Protonation of the other OH would lead to the less stable secondary carbocation and this will not be favored.
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Unformatted text preview: Now what? You know from the answer that you must make a five-membered ring, so the ring must contract. What happens if it does? CH 3 OH CH 3 OH = CH 3 OH At first, this may seem unfavorable. But then you notice the resonance stabilization, and all is well. A deprotonation leads to the product. CH 3 O CH 3 O CH 3 O H H H H 2 O...
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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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