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Quick Organic Chem

  1. Aug 25, 2015 #1
    1. The problem statement, all variables and given/known data
    ______________Stgae 1

    P:C3H6O ----->
    _________________Br2 in organic solvent
    Q:C3H6OBr2
    Stage 2
    -->R:C3H5Br3
    1.What is the structural formular of P and Q respectively???
    2.What is the reagents in the conversion of Q to R??
    (1) Phosphorous tribromide liquid
    (2) Bromine liquid
    (3) Solid Potassium bromide and concentrated sulphuric acid
    Which one can??


    3. The attempt at a solution
    Are there two possible structures for P. One is 1,2-dibromopropenol and
    2,3-dibromopropenol. My answer is 1,2-dibromopropenol.However someone told me that 2,3-dibromopropenol is the answer as Bromine atoms cannot add to carbon atom with hydroxyl group, whywhywhywhy???????

    I totally have no idea for question 2....... lol
     
    Last edited: Aug 25, 2015
  2. jcsd
  3. Aug 25, 2015 #2

    Ygggdrasil

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    Last edited: Aug 25, 2015
  4. Aug 25, 2015 #3
    Hi, first of all, what do you think P and Q are? And how did P become Q?

    There are many ways for Q to become R, such as:
    i) react P(s) + Br2 in situ
    ii) NaBr (s) + h2so4 (conc), heat
    iii) react with HBr (g), room temp. or HBr (aq) conc., heat

    And about 1,2-dibromopropanol, are you regarding to Q I'm assuming you mean Q anyways. Well, it not only can be 1,2- , it can also be 1,1- , 2,2- . But think about 2,3- ...Isn't it the same with 1,2- ?? Since there are only 3 Carbons? Or do you mean why can't it be 1,2- bromopropan-1-ol instead of 1,2-bromopropan-3-ol?

    May I know where did you get this question from? If can, can you show us a picture of the full question, it'll help a lot.
     
  5. Aug 27, 2015 #4

    Merlin3189

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    Gold Member

    I'm only a non-chemist with a casual interest, but can I make one suggestion?

    For part 2, what do you think the other product of the reaction is?
    ie. Q + part of reagent -> R + what?
    Does that give you a clue to what the reagent must be?


    [Can I also just wonder why people are talking about "enols" ? I had assumed at first that it was just a mis-spelling (or foreign spelling) for propane or propanol?]- edited below
    On second thoughts (after half an hour!) scrub this bit. I just assumed it was 1-propanal and did not think about other possibilities. Looking at the reaction, may be other candidates are more likely.
     
    Last edited: Aug 27, 2015
  6. Sep 1, 2015 #5
    Hi, do you understand my explanations? Please reply to us thanks.
     
  7. Sep 1, 2015 #6
    "enol" is a chemical term.
     
  8. Sep 2, 2015 #7

    Merlin3189

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    Gold Member

    Yes I did look it up (though I'm not sure I understood what I found!)
    I was originally puzzled because it had sounded to me like an alcohol based on an alkene, whereas the original substance looked to me like an aldehyde of an alkane (propanaldehyde?).
    I did go back and edit my post when I realised that there were more complex possibilities, including a C=C, but left my original comment in brackets so as not to confuse anyone who had read it in the meantime. Now, of course, I wish I'd not said it, as it is irrelevant to the OP question.

    I'm sorry the thread has dried up, as I would have liked to know what the real answer is! I thought at first you could only solve it if you guessed the original compound correctly, but now I wonder if you have to work backwards from the Q and R ?
    I am positioning the Cl 's on the basis that they are very electrophillic and will go where electrons are most available (a bit of naive physics!) This would not prevent them going on the C with the O, but since O is also electrophillic, that C would be short of electrons so they would be less likely to go there.
     
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