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Addition reaction to produce 3-methyl-3-hexanol

  1. Oct 19, 2017 #1
    1. The problem statement, all variables and given/known data
    Write a chemical equation for addition reactions to produce 3-methyl-3-hexanol.
    Condensed structural formulas should be used for each organic compound.


    2. Relevant equations
    none

    3. The attempt at a solution
    https://i.imgur.com/REIpKHK.jpg

    REIpKHK.jpg

    Is this correct? My friend tried explaining this to me but I still don't really understand it. I would like to practice some on my own but I can't find anything online explaining how to do it in the first place. Any help would be appreciated, thanks!
     
  2. jcsd
  3. Oct 19, 2017 #2

    TeethWhitener

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    Can you draw out a mechanism for how you think the initial addition steps will take place?
     
  4. Oct 24, 2017 #3
    Hey, sorry for the late response.

    So to get 3-methyl-3-hexanol I must add HOH to 3-methyl-3-hexene.

    In my lesson I am told that the hydrogen atom of water would be added to the carbon that already has more hydrogens. I'm not sure if that means the hydrogen atom would be added to the CH2 to the left of the central carbon, or if it would be added to the CH to the right of the central carbon where the double bond is (if this doesnt make sense I can try to draw it out). I am also told that the OH of water would be added to the central carbon atom, which I did.
     
  5. Oct 24, 2017 #4

    TeethWhitener

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    Let’s tackle the issues one at a time. What type of species adds to alkenes? Nucleophilic (partially negatively charged) or electrophilic (partially positively charged)?
     
  6. Oct 25, 2017 #5
    Electrophilic
     
  7. Oct 25, 2017 #6

    TeethWhitener

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    Ok so if you are adding H2O, which part will attack the double bond?
     
  8. Oct 25, 2017 #7
    Hydrogen would attack the double bond because it is positive.
     
  9. Oct 25, 2017 #8

    TeethWhitener

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    And how would this change the alkene species?
     
  10. Oct 25, 2017 #9
    Does it become a single bond instead of a double bond?
     
  11. Oct 25, 2017 #10

    TeethWhitener

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    Consider a generic alkene: R2C=CR2 (doesn’t have to be symmetric). If you add a charged species like H+, you have to end up with a charged species, right? What does that charged species look like? (What element in the alkene ends up with the charge, If you were to do arrow pushing?)
     
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