Problem: Write a mechanism for the following reaction.

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We’re being asked to determine the most stable intermediate of the given reaction.



Recall that alkenes are converted to alcohols via acid-catalyzed hydration, which occurs in three steps:

(1) protonation – the alkene is protonated by the acid catalyst, forming a carbocation intermediate. This follows Markovnikov’s rule, which states that the more stable carbocation is formed.


Also, since a carbocation is formed during the reaction, the carbocation may rearrange into a more stable one.


(2) nucleophilic attack – water in and attacks the positively-charged carbon. The stereochemistry for this reaction is unknown since the nucleophile can attack either side of the empty p-orbital.


(3) deprotonation – the conjugate base deprotonates the oxonium ion, reforming the acid catalyst.


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Write a mechanism for the following reaction.