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Posted by on Thursday, January 24, 2013 at 8:21pm.

what is this compound, it has a mf of c6h12o i. imgur. com/gCgw0Hi. png

  • organic chemistry - , Thursday, January 24, 2013 at 9:27pm

    The IR shows a bird wing at about 3500, so we know we have an OH group, and the degree of unsaturation is 2, so we have 2 double bonds or a triple bond.


    I am no where near positive, but I believe that the answer is
    H
    I
    CH3-C=C
    I I
    CH3-C=C CH3
    I I
    H OH

    This accounts for the splitting patterns that I see in H NMR, but some of the placements of the peaks kind of bug me, so I am not sure. I haven't done this in a while, so hopefully someone else comes along and gives their input. Hope this helps.

  • organic chemistry - , Thursday, January 24, 2013 at 9:34pm

    The IR shows a bird wing at about 3500, so we know we have an OH group, and the degree of unsaturation is 2, so we have 2 double bonds or a triple bond.


    I am no where near positive, but I believe that the answer is


    CH3
    CH3--CH=C--C=C--CH3
    OH H

    This accounts for the splitting patterns that I see in H NMR, but some of the placements of the peaks kind of bug me, so I am not sure. I haven't done this in a while, so hopefully someone else comes along and gives their input. Hope this helps.

  • organic chemistry - , Thursday, January 24, 2013 at 9:38pm

    there is only 1 degree of unsaturation

  • organic chemistry - , Thursday, January 24, 2013 at 9:39pm

    The CH3, H, and OH group are connected to the structure I tried to type in the middle of this mess. The top CH3 goes with the fourth carbon (a covalent bond) from the left, the OH goes with the third carbon from the left, and the hydrogen goes with the fifth carbon from the left.

  • organic chemistry - , Thursday, January 24, 2013 at 9:42pm

    D of Unsaturation =[(2 +(2 x number of carbons(6))-12]=2

  • organic chemistry - , Thursday, January 24, 2013 at 9:43pm

    you divide that by 2 so it's 1

  • organic chemistry - , Thursday, January 24, 2013 at 9:52pm

    your correct.

  • organic chemistry - , Thursday, January 24, 2013 at 10:08pm

    Like I said I'm not sure, but it looks like this may be
    2,3-dimethyl-cyclopropanol. This would account for the splitting problem, but since I am not sure I wouldn't bet money on it.

  • organic chemistry - , Thursday, January 24, 2013 at 10:16pm

    This gave me a headache. I'm sorry, 1,2,- trimethyl-cyclopropanol.

  • organic chemistry - , Thursday, January 24, 2013 at 10:17pm

    1,23,- trimethyl-cyclopropanol.

  • organic chemistry - , Thursday, January 24, 2013 at 10:36pm

    This is bugging me, because I'm not sure. the peaks for d and e should show splitting, but they don't. The only structure that I can think of is 2,3,3-trimethyl-cyclopropanol. Hopefully someone else comes along and is of some assistance. Post the right answer if you can; I am very curious about this one.

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