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Chemistry 13 Online
OpenStudy (anonymous):

Mechanisme help!!

OpenStudy (anonymous):

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OpenStudy (anonymous):

i can't see the product clearly, but i am guessing the following sequence took place: 1. protonation on the least substituted (rightmost) sp2 carbon, and formation of a secondary carbocation. 2a. proton transfer from the tertiary carbon to the carbon bearing the positive charge. this is the first rearrangement. 2b. intramolecular nucleophile attack by the benzene ring, pick the pi bond adjacent to the substituent. this is another sort of rearrangement. 3. now we have a created five-membered ring, and the positive charge is on a tertiary carbon. deprotonation by a water molecule restores the aromaticity. looks like this reaction is going to be really slow, because there are several intermediate carbocations, and step 2b breaks the aromaticity.

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