I am having some trouble understanding the behaviors of some Alkene reactions that I have been studying. I took two semesters of O-chem a couple of years ago and am trying to refresh before an advanced class, but I have found two reactions in my studies that aren't making sense.

At the top of page 13 of the e-book found here: http://crab.rutgers.edu/~alroche/Ch08.pdf ... I see that the water molecule is attacking the carbon with two methyl groups on it... but wouldn't the carbon with only one methyl group be more electrophyllic? Because of induction, I would think that the carbon with two methyl groups would be more stable than the other, and so the carbon with less substituents would be more electron-poor.... So why does the water attack the more substituted carbon?

Secondly, in the image below (sorry it's turned), where the second proton transfer is taking place, you see the water molecule pulling the hydrogen off of the more substituted carbon. But wouldn't the hydrogens on the methyl group adjacent to the positive charge be way more electrophyllic, thus creating a double bond on the end of the chain?

I appreciate any help on this. Thanks for your time and effort!

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  • $\begingroup$ These are both fairly standard questions which will be answered by any good organic chemistry text in detail. If you have access, Warren & Clayden- Organic Chemistry is excellent. $\endgroup$
    – NotEvans.
    Jul 21, 2016 at 18:23
  • $\begingroup$ I have been searching in my textbook and online. My textbook does not seem to explain it well, and it has been very difficult to find online due to the very specific questions I am asking. That was why I came here. $\endgroup$
    – BTrem
    Jul 21, 2016 at 20:30
  • $\begingroup$ I have a copy of the book I mentioned in front of me, the questions are answered in any undergraduate text (i.e. not very specific at all). But I dont mind trying to answer if that would help, I think my point was that a decent book would probably do it more succinctly $\endgroup$
    – NotEvans.
    Jul 21, 2016 at 20:32

1 Answer 1


Water can attack both carbocation and hydrogen atom. Sometimes it attacks C, sometimes it attacks H.

Whenever it attacks C alcohol forms so the reaction goes back to reactants. When it attacks H the product forms. We are interested in product, so we show only this path.


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