Largest alkane having a given alkane as its base name












3












$begingroup$


What is the largest (most carbon atoms) alkane having heptane as its base name?

For example, 2,2,3,3-tetramethylbutane is the largest (most carbon atoms) alkane retaining butane as its base name.






organic-chemistry nomenclature







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$endgroup$








  • 1




    $begingroup$
    You put as many side chains on it as possible without creating a new longest chain. Then you do the same with each of the side chains, and then you hope that the final molecule's center hasn't become so dense that it snaps in two.
    $endgroup$
    – Karl
    6 hours ago










  • $begingroup$
    This is a subset of a very interesting theoretical question about how many isomers are possible for simple hydrocarbons discussed in this question: chemistry.stackexchange.com/q/16135/81 . Answers there also address questions about whether potential molecules are physically possible.
    $endgroup$
    – matt_black
    5 hours ago
















3












$begingroup$


What is the largest (most carbon atoms) alkane having heptane as its base name?

For example, 2,2,3,3-tetramethylbutane is the largest (most carbon atoms) alkane retaining butane as its base name.






organic-chemistry nomenclature







share|improve this question











$endgroup$








  • 1




    $begingroup$
    You put as many side chains on it as possible without creating a new longest chain. Then you do the same with each of the side chains, and then you hope that the final molecule's center hasn't become so dense that it snaps in two.
    $endgroup$
    – Karl
    6 hours ago










  • $begingroup$
    This is a subset of a very interesting theoretical question about how many isomers are possible for simple hydrocarbons discussed in this question: chemistry.stackexchange.com/q/16135/81 . Answers there also address questions about whether potential molecules are physically possible.
    $endgroup$
    – matt_black
    5 hours ago














3












3








3


1



$begingroup$


What is the largest (most carbon atoms) alkane having heptane as its base name?

For example, 2,2,3,3-tetramethylbutane is the largest (most carbon atoms) alkane retaining butane as its base name.






organic-chemistry nomenclature







share|improve this question











$endgroup$




What is the largest (most carbon atoms) alkane having heptane as its base name?

For example, 2,2,3,3-tetramethylbutane is the largest (most carbon atoms) alkane retaining butane as its base name.






organic-chemistry nomenclature




organic-chemistry nomenclature






share|improve this question















share|improve this question













share|improve this question




share|improve this question








edited 2 hours ago









Karl

5,5751329




5,5751329










asked 7 hours ago









Nandakumar U KNandakumar U K

227




227








  • 1




    $begingroup$
    You put as many side chains on it as possible without creating a new longest chain. Then you do the same with each of the side chains, and then you hope that the final molecule's center hasn't become so dense that it snaps in two.
    $endgroup$
    – Karl
    6 hours ago










  • $begingroup$
    This is a subset of a very interesting theoretical question about how many isomers are possible for simple hydrocarbons discussed in this question: chemistry.stackexchange.com/q/16135/81 . Answers there also address questions about whether potential molecules are physically possible.
    $endgroup$
    – matt_black
    5 hours ago














  • 1




    $begingroup$
    You put as many side chains on it as possible without creating a new longest chain. Then you do the same with each of the side chains, and then you hope that the final molecule's center hasn't become so dense that it snaps in two.
    $endgroup$
    – Karl
    6 hours ago










  • $begingroup$
    This is a subset of a very interesting theoretical question about how many isomers are possible for simple hydrocarbons discussed in this question: chemistry.stackexchange.com/q/16135/81 . Answers there also address questions about whether potential molecules are physically possible.
    $endgroup$
    – matt_black
    5 hours ago








1




1




$begingroup$
You put as many side chains on it as possible without creating a new longest chain. Then you do the same with each of the side chains, and then you hope that the final molecule's center hasn't become so dense that it snaps in two.
$endgroup$
– Karl
6 hours ago




$begingroup$
You put as many side chains on it as possible without creating a new longest chain. Then you do the same with each of the side chains, and then you hope that the final molecule's center hasn't become so dense that it snaps in two.
$endgroup$
– Karl
6 hours ago












$begingroup$
This is a subset of a very interesting theoretical question about how many isomers are possible for simple hydrocarbons discussed in this question: chemistry.stackexchange.com/q/16135/81 . Answers there also address questions about whether potential molecules are physically possible.
$endgroup$
– matt_black
5 hours ago




$begingroup$
This is a subset of a very interesting theoretical question about how many isomers are possible for simple hydrocarbons discussed in this question: chemistry.stackexchange.com/q/16135/81 . Answers there also address questions about whether potential molecules are physically possible.
$endgroup$
– matt_black
5 hours ago










2 Answers
2






active

oldest

votes


















7












$begingroup$

Any alkyl substituent of butane in position 2 or 3 cannot be longer than $ce{CH3}$ since that would lead to a longer parent chain. And obviously, there cannot be any alkyl substituent at all in the first or the last position of the butane chain. Therefore, the largest structure based on a butane parent chain is 2,2,3,3-tetramethylbutane.



This principle can be expanded to a heptane parent chain. The maximum length for alkyl substituent chains are 0 for position 1 and 7, 1 for position 2 and 6, 2 for position 3 and 5, and 3 for position 4. Therefore, the largest theoretical structure based on a heptane parent chain is 3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane ($ce{C53H108}$).



3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane






share|improve this answer











$endgroup$









  • 1




    $begingroup$
    I believe this thing is much too crowded to survive, but then again, that's not what the question was about. Other than that, you are right.
    $endgroup$
    – Ivan Neretin
    6 hours ago






  • 1




    $begingroup$
    @IvanNeretin Agreed, the inner C–C bonds would probably be stretched to more than 2 Å. That’s why I wrote “largest theoretical structure”.
    $endgroup$
    – Loong♦
    6 hours ago












  • $begingroup$
    @Loong make that definitely. ;-)
    $endgroup$
    – Karl
    6 hours ago










  • $begingroup$
    My head hurts trying to parse that name. Could you draw it and give its simple overall formula? Then I can look it up on the list given in answers to chemistry.stackexchange.com/q/16135/81
    $endgroup$
    – matt_black
    5 hours ago






  • 1




    $begingroup$
    Preferred IUPAC names is a good concept, but “tetrakis(tri-tert-butylmethyl)methane” is somewhat shorter and clearer ;)
    $endgroup$
    – mykhal
    2 hours ago





















5












$begingroup$

That's hard to tell, because already tetra-tert-butylmethane (3,3-di-tert-butyl-2,2,4,4-tetramethylpentane) is so unstable it cannot exist. You want a parent chain that is even two atoms longer.



Actually it seems also removing one methyl group from $ce{tBu_4}$methane doesn't make it sufficiently stable, so one has to be a bit more generous in weeding out branches for larger hyperbranched alkanes.



I believe that any permethylated (or per-n-alkylated) linear chain is principally possible, but adding more side-side chains to adjacent side chains will make the molecule snap in two.



So the biggest possible sum formula would be something based on



3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C23H48}$



. You can surely make the inner methyl substituents longer,



3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C29H60}$



, and then you can probably add 4 methly to the nPr and Et to give iBu and i-Pr that's $ce{C33H68}$. Any more and I'll bet it breaks, quite a way from the theoretical $ce{C53H108}$.






share|improve this answer











$endgroup$













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    2 Answers
    2






    active

    oldest

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    2 Answers
    2






    active

    oldest

    votes









    active

    oldest

    votes






    active

    oldest

    votes









    7












    $begingroup$

    Any alkyl substituent of butane in position 2 or 3 cannot be longer than $ce{CH3}$ since that would lead to a longer parent chain. And obviously, there cannot be any alkyl substituent at all in the first or the last position of the butane chain. Therefore, the largest structure based on a butane parent chain is 2,2,3,3-tetramethylbutane.



    This principle can be expanded to a heptane parent chain. The maximum length for alkyl substituent chains are 0 for position 1 and 7, 1 for position 2 and 6, 2 for position 3 and 5, and 3 for position 4. Therefore, the largest theoretical structure based on a heptane parent chain is 3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane ($ce{C53H108}$).



    3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane






    share|improve this answer











    $endgroup$









    • 1




      $begingroup$
      I believe this thing is much too crowded to survive, but then again, that's not what the question was about. Other than that, you are right.
      $endgroup$
      – Ivan Neretin
      6 hours ago






    • 1




      $begingroup$
      @IvanNeretin Agreed, the inner C–C bonds would probably be stretched to more than 2 Å. That’s why I wrote “largest theoretical structure”.
      $endgroup$
      – Loong♦
      6 hours ago












    • $begingroup$
      @Loong make that definitely. ;-)
      $endgroup$
      – Karl
      6 hours ago










    • $begingroup$
      My head hurts trying to parse that name. Could you draw it and give its simple overall formula? Then I can look it up on the list given in answers to chemistry.stackexchange.com/q/16135/81
      $endgroup$
      – matt_black
      5 hours ago






    • 1




      $begingroup$
      Preferred IUPAC names is a good concept, but “tetrakis(tri-tert-butylmethyl)methane” is somewhat shorter and clearer ;)
      $endgroup$
      – mykhal
      2 hours ago


















    7












    $begingroup$

    Any alkyl substituent of butane in position 2 or 3 cannot be longer than $ce{CH3}$ since that would lead to a longer parent chain. And obviously, there cannot be any alkyl substituent at all in the first or the last position of the butane chain. Therefore, the largest structure based on a butane parent chain is 2,2,3,3-tetramethylbutane.



    This principle can be expanded to a heptane parent chain. The maximum length for alkyl substituent chains are 0 for position 1 and 7, 1 for position 2 and 6, 2 for position 3 and 5, and 3 for position 4. Therefore, the largest theoretical structure based on a heptane parent chain is 3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane ($ce{C53H108}$).



    3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane






    share|improve this answer











    $endgroup$









    • 1




      $begingroup$
      I believe this thing is much too crowded to survive, but then again, that's not what the question was about. Other than that, you are right.
      $endgroup$
      – Ivan Neretin
      6 hours ago






    • 1




      $begingroup$
      @IvanNeretin Agreed, the inner C–C bonds would probably be stretched to more than 2 Å. That’s why I wrote “largest theoretical structure”.
      $endgroup$
      – Loong♦
      6 hours ago












    • $begingroup$
      @Loong make that definitely. ;-)
      $endgroup$
      – Karl
      6 hours ago










    • $begingroup$
      My head hurts trying to parse that name. Could you draw it and give its simple overall formula? Then I can look it up on the list given in answers to chemistry.stackexchange.com/q/16135/81
      $endgroup$
      – matt_black
      5 hours ago






    • 1




      $begingroup$
      Preferred IUPAC names is a good concept, but “tetrakis(tri-tert-butylmethyl)methane” is somewhat shorter and clearer ;)
      $endgroup$
      – mykhal
      2 hours ago
















    7












    7








    7





    $begingroup$

    Any alkyl substituent of butane in position 2 or 3 cannot be longer than $ce{CH3}$ since that would lead to a longer parent chain. And obviously, there cannot be any alkyl substituent at all in the first or the last position of the butane chain. Therefore, the largest structure based on a butane parent chain is 2,2,3,3-tetramethylbutane.



    This principle can be expanded to a heptane parent chain. The maximum length for alkyl substituent chains are 0 for position 1 and 7, 1 for position 2 and 6, 2 for position 3 and 5, and 3 for position 4. Therefore, the largest theoretical structure based on a heptane parent chain is 3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane ($ce{C53H108}$).



    3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane






    share|improve this answer











    $endgroup$



    Any alkyl substituent of butane in position 2 or 3 cannot be longer than $ce{CH3}$ since that would lead to a longer parent chain. And obviously, there cannot be any alkyl substituent at all in the first or the last position of the butane chain. Therefore, the largest structure based on a butane parent chain is 2,2,3,3-tetramethylbutane.



    This principle can be expanded to a heptane parent chain. The maximum length for alkyl substituent chains are 0 for position 1 and 7, 1 for position 2 and 6, 2 for position 3 and 5, and 3 for position 4. Therefore, the largest theoretical structure based on a heptane parent chain is 3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane ($ce{C53H108}$).



    3,3,5,5-tetra-tert-butyl-4,4-bis[3-(tert-butyl)-2,2,4,4-tetramethylpentan-3-yl]-2,2,6,6-tetramethylheptane







    share|improve this answer














    share|improve this answer



    share|improve this answer








    edited 4 hours ago

























    answered 6 hours ago









    Loong♦Loong

    32.9k881168




    32.9k881168








    • 1




      $begingroup$
      I believe this thing is much too crowded to survive, but then again, that's not what the question was about. Other than that, you are right.
      $endgroup$
      – Ivan Neretin
      6 hours ago






    • 1




      $begingroup$
      @IvanNeretin Agreed, the inner C–C bonds would probably be stretched to more than 2 Å. That’s why I wrote “largest theoretical structure”.
      $endgroup$
      – Loong♦
      6 hours ago












    • $begingroup$
      @Loong make that definitely. ;-)
      $endgroup$
      – Karl
      6 hours ago










    • $begingroup$
      My head hurts trying to parse that name. Could you draw it and give its simple overall formula? Then I can look it up on the list given in answers to chemistry.stackexchange.com/q/16135/81
      $endgroup$
      – matt_black
      5 hours ago






    • 1




      $begingroup$
      Preferred IUPAC names is a good concept, but “tetrakis(tri-tert-butylmethyl)methane” is somewhat shorter and clearer ;)
      $endgroup$
      – mykhal
      2 hours ago
















    • 1




      $begingroup$
      I believe this thing is much too crowded to survive, but then again, that's not what the question was about. Other than that, you are right.
      $endgroup$
      – Ivan Neretin
      6 hours ago






    • 1




      $begingroup$
      @IvanNeretin Agreed, the inner C–C bonds would probably be stretched to more than 2 Å. That’s why I wrote “largest theoretical structure”.
      $endgroup$
      – Loong♦
      6 hours ago












    • $begingroup$
      @Loong make that definitely. ;-)
      $endgroup$
      – Karl
      6 hours ago










    • $begingroup$
      My head hurts trying to parse that name. Could you draw it and give its simple overall formula? Then I can look it up on the list given in answers to chemistry.stackexchange.com/q/16135/81
      $endgroup$
      – matt_black
      5 hours ago






    • 1




      $begingroup$
      Preferred IUPAC names is a good concept, but “tetrakis(tri-tert-butylmethyl)methane” is somewhat shorter and clearer ;)
      $endgroup$
      – mykhal
      2 hours ago










    1




    1




    $begingroup$
    I believe this thing is much too crowded to survive, but then again, that's not what the question was about. Other than that, you are right.
    $endgroup$
    – Ivan Neretin
    6 hours ago




    $begingroup$
    I believe this thing is much too crowded to survive, but then again, that's not what the question was about. Other than that, you are right.
    $endgroup$
    – Ivan Neretin
    6 hours ago




    1




    1




    $begingroup$
    @IvanNeretin Agreed, the inner C–C bonds would probably be stretched to more than 2 Å. That’s why I wrote “largest theoretical structure”.
    $endgroup$
    – Loong♦
    6 hours ago






    $begingroup$
    @IvanNeretin Agreed, the inner C–C bonds would probably be stretched to more than 2 Å. That’s why I wrote “largest theoretical structure”.
    $endgroup$
    – Loong♦
    6 hours ago














    $begingroup$
    @Loong make that definitely. ;-)
    $endgroup$
    – Karl
    6 hours ago




    $begingroup$
    @Loong make that definitely. ;-)
    $endgroup$
    – Karl
    6 hours ago












    $begingroup$
    My head hurts trying to parse that name. Could you draw it and give its simple overall formula? Then I can look it up on the list given in answers to chemistry.stackexchange.com/q/16135/81
    $endgroup$
    – matt_black
    5 hours ago




    $begingroup$
    My head hurts trying to parse that name. Could you draw it and give its simple overall formula? Then I can look it up on the list given in answers to chemistry.stackexchange.com/q/16135/81
    $endgroup$
    – matt_black
    5 hours ago




    1




    1




    $begingroup$
    Preferred IUPAC names is a good concept, but “tetrakis(tri-tert-butylmethyl)methane” is somewhat shorter and clearer ;)
    $endgroup$
    – mykhal
    2 hours ago






    $begingroup$
    Preferred IUPAC names is a good concept, but “tetrakis(tri-tert-butylmethyl)methane” is somewhat shorter and clearer ;)
    $endgroup$
    – mykhal
    2 hours ago













    5












    $begingroup$

    That's hard to tell, because already tetra-tert-butylmethane (3,3-di-tert-butyl-2,2,4,4-tetramethylpentane) is so unstable it cannot exist. You want a parent chain that is even two atoms longer.



    Actually it seems also removing one methyl group from $ce{tBu_4}$methane doesn't make it sufficiently stable, so one has to be a bit more generous in weeding out branches for larger hyperbranched alkanes.



    I believe that any permethylated (or per-n-alkylated) linear chain is principally possible, but adding more side-side chains to adjacent side chains will make the molecule snap in two.



    So the biggest possible sum formula would be something based on



    3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C23H48}$



    . You can surely make the inner methyl substituents longer,



    3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C29H60}$



    , and then you can probably add 4 methly to the nPr and Et to give iBu and i-Pr that's $ce{C33H68}$. Any more and I'll bet it breaks, quite a way from the theoretical $ce{C53H108}$.






    share|improve this answer











    $endgroup$


















      5












      $begingroup$

      That's hard to tell, because already tetra-tert-butylmethane (3,3-di-tert-butyl-2,2,4,4-tetramethylpentane) is so unstable it cannot exist. You want a parent chain that is even two atoms longer.



      Actually it seems also removing one methyl group from $ce{tBu_4}$methane doesn't make it sufficiently stable, so one has to be a bit more generous in weeding out branches for larger hyperbranched alkanes.



      I believe that any permethylated (or per-n-alkylated) linear chain is principally possible, but adding more side-side chains to adjacent side chains will make the molecule snap in two.



      So the biggest possible sum formula would be something based on



      3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C23H48}$



      . You can surely make the inner methyl substituents longer,



      3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C29H60}$



      , and then you can probably add 4 methly to the nPr and Et to give iBu and i-Pr that's $ce{C33H68}$. Any more and I'll bet it breaks, quite a way from the theoretical $ce{C53H108}$.






      share|improve this answer











      $endgroup$
















        5












        5








        5





        $begingroup$

        That's hard to tell, because already tetra-tert-butylmethane (3,3-di-tert-butyl-2,2,4,4-tetramethylpentane) is so unstable it cannot exist. You want a parent chain that is even two atoms longer.



        Actually it seems also removing one methyl group from $ce{tBu_4}$methane doesn't make it sufficiently stable, so one has to be a bit more generous in weeding out branches for larger hyperbranched alkanes.



        I believe that any permethylated (or per-n-alkylated) linear chain is principally possible, but adding more side-side chains to adjacent side chains will make the molecule snap in two.



        So the biggest possible sum formula would be something based on



        3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C23H48}$



        . You can surely make the inner methyl substituents longer,



        3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C29H60}$



        , and then you can probably add 4 methly to the nPr and Et to give iBu and i-Pr that's $ce{C33H68}$. Any more and I'll bet it breaks, quite a way from the theoretical $ce{C53H108}$.






        share|improve this answer











        $endgroup$



        That's hard to tell, because already tetra-tert-butylmethane (3,3-di-tert-butyl-2,2,4,4-tetramethylpentane) is so unstable it cannot exist. You want a parent chain that is even two atoms longer.



        Actually it seems also removing one methyl group from $ce{tBu_4}$methane doesn't make it sufficiently stable, so one has to be a bit more generous in weeding out branches for larger hyperbranched alkanes.



        I believe that any permethylated (or per-n-alkylated) linear chain is principally possible, but adding more side-side chains to adjacent side chains will make the molecule snap in two.



        So the biggest possible sum formula would be something based on



        3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C23H48}$



        . You can surely make the inner methyl substituents longer,



        3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C29H60}$



        , and then you can probably add 4 methly to the nPr and Et to give iBu and i-Pr that's $ce{C33H68}$. Any more and I'll bet it breaks, quite a way from the theoretical $ce{C53H108}$.







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        edited 2 hours ago

























        answered 6 hours ago









        KarlKarl

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