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Homework Help: Organic Chem- acid catalyzed reation

  1. Feb 7, 2006 #1
    Hey can anyone help me with this question?

    What is the major product from the acid-catalyzed hydration of 3-methyl-2-pentene?

    a. 3-methylpentane
    b. 3-methyl-1-pentanol
    c. 3-methyl-2-pentanol
    d. 3-methyl-3-pentanol
    e. 3-methoxypentane

    Would the answer by D? My reasoning is that when that OH- group bonds to the third carbon, that carbon will be bonded to 4 substituents, which is very stable. Is this correct?
  2. jcsd
  3. Feb 7, 2006 #2
    the one rule to remember from all of O chem is the fact that tertiary carbocations are the most stable.
  4. Mar 29, 2006 #3


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    actually you are mistaken, tertiary carbocations are not the most stable

    The order is as follows:

    Substituded Allylic> 3 > Allylic > 2 >1 >Vinylic > Methyl
  5. Mar 29, 2006 #4


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    Science Advisor

    Well, if you really want to be specific you'd better include benzyllic, doubly allylic, doubly benzylic, triply allylic, triply benzyllic, cations stabilized by adjacent heteroatoms, non-classical carbocations, cations destabilized by inductive withdrawing groups, and on and on....
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