Highest alkane for a given parent alkane












2












$begingroup$


Would please somebody tell what is the highest alkane having heptane as the parent chain? For instance butane can have 2,2,3,3-tetramethylbutane as the highest possibility retaining butane as the parent. So
$ce{C8H18}$.






isomers






share











$endgroup$












  • $begingroup$
    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
    2 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
    1 hour ago
















2












$begingroup$


Would please somebody tell what is the highest alkane having heptane as the parent chain? For instance butane can have 2,2,3,3-tetramethylbutane as the highest possibility retaining butane as the parent. So
$ce{C8H18}$.






isomers






share











$endgroup$












  • $begingroup$
    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
    2 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
    1 hour ago














2












2








2





$begingroup$


Would please somebody tell what is the highest alkane having heptane as the parent chain? For instance butane can have 2,2,3,3-tetramethylbutane as the highest possibility retaining butane as the parent. So
$ce{C8H18}$.






isomers






share











$endgroup$




Would please somebody tell what is the highest alkane having heptane as the parent chain? For instance butane can have 2,2,3,3-tetramethylbutane as the highest possibility retaining butane as the parent. So
$ce{C8H18}$.






isomers




isomers





share














share












share



share








edited 2 hours ago









Karl

5,5351329




5,5351329










asked 3 hours ago









Nandakumar U KNandakumar U K

176




176












  • $begingroup$
    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
    2 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
    1 hour 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
    2 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
    1 hour 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
2 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
2 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
1 hour 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
1 hour ago










2 Answers
2






active

oldest

votes


















3












$begingroup$

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
    2 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♦
    2 hours ago












  • $begingroup$
    @Loong make that definitely. ;-)
    $endgroup$
    – Karl
    1 hour 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
    59 mins ago










  • $begingroup$
    @matt_black It replaces any of the 12 Me groups of tetra-tBu-methane by tBu, so it's $ce{C5 + 12 * C4H9 = C53H108}$. Too many isomers to even think about. ;-)
    $endgroup$
    – Karl
    48 mins ago





















2












$begingroup$

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.



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 somewhere in the range of



3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C21H44}$



. A bit more, because you can likely make the inner methyl substituents longer,



3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C25H52}$



, and then you can enlarge probably the nPr and Et to iBu and s-Bu that's $ce{C29H60}$. Any more and I'll bet it breaks.






share|improve this answer











$endgroup$













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    2 Answers
    2






    active

    oldest

    votes








    2 Answers
    2






    active

    oldest

    votes









    active

    oldest

    votes






    active

    oldest

    votes









    3












    $begingroup$

    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
      2 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♦
      2 hours ago












    • $begingroup$
      @Loong make that definitely. ;-)
      $endgroup$
      – Karl
      1 hour 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
      59 mins ago










    • $begingroup$
      @matt_black It replaces any of the 12 Me groups of tetra-tBu-methane by tBu, so it's $ce{C5 + 12 * C4H9 = C53H108}$. Too many isomers to even think about. ;-)
      $endgroup$
      – Karl
      48 mins ago


















    3












    $begingroup$

    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
      2 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♦
      2 hours ago












    • $begingroup$
      @Loong make that definitely. ;-)
      $endgroup$
      – Karl
      1 hour 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
      59 mins ago










    • $begingroup$
      @matt_black It replaces any of the 12 Me groups of tetra-tBu-methane by tBu, so it's $ce{C5 + 12 * C4H9 = C53H108}$. Too many isomers to even think about. ;-)
      $endgroup$
      – Karl
      48 mins ago
















    3












    3








    3





    $begingroup$

    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 44 mins ago

























    answered 2 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
      2 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♦
      2 hours ago












    • $begingroup$
      @Loong make that definitely. ;-)
      $endgroup$
      – Karl
      1 hour 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
      59 mins ago










    • $begingroup$
      @matt_black It replaces any of the 12 Me groups of tetra-tBu-methane by tBu, so it's $ce{C5 + 12 * C4H9 = C53H108}$. Too many isomers to even think about. ;-)
      $endgroup$
      – Karl
      48 mins 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
      2 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♦
      2 hours ago












    • $begingroup$
      @Loong make that definitely. ;-)
      $endgroup$
      – Karl
      1 hour 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
      59 mins ago










    • $begingroup$
      @matt_black It replaces any of the 12 Me groups of tetra-tBu-methane by tBu, so it's $ce{C5 + 12 * C4H9 = C53H108}$. Too many isomers to even think about. ;-)
      $endgroup$
      – Karl
      48 mins 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
    2 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
    2 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♦
    2 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♦
    2 hours ago














    $begingroup$
    @Loong make that definitely. ;-)
    $endgroup$
    – Karl
    1 hour ago




    $begingroup$
    @Loong make that definitely. ;-)
    $endgroup$
    – Karl
    1 hour 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
    59 mins 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
    59 mins ago












    $begingroup$
    @matt_black It replaces any of the 12 Me groups of tetra-tBu-methane by tBu, so it's $ce{C5 + 12 * C4H9 = C53H108}$. Too many isomers to even think about. ;-)
    $endgroup$
    – Karl
    48 mins ago






    $begingroup$
    @matt_black It replaces any of the 12 Me groups of tetra-tBu-methane by tBu, so it's $ce{C5 + 12 * C4H9 = C53H108}$. Too many isomers to even think about. ;-)
    $endgroup$
    – Karl
    48 mins ago













    2












    $begingroup$

    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.



    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 somewhere in the range of



    3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C21H44}$



    . A bit more, because you can likely make the inner methyl substituents longer,



    3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C25H52}$



    , and then you can enlarge probably the nPr and Et to iBu and s-Bu that's $ce{C29H60}$. Any more and I'll bet it breaks.






    share|improve this answer











    $endgroup$


















      2












      $begingroup$

      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.



      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 somewhere in the range of



      3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C21H44}$



      . A bit more, because you can likely make the inner methyl substituents longer,



      3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C25H52}$



      , and then you can enlarge probably the nPr and Et to iBu and s-Bu that's $ce{C29H60}$. Any more and I'll bet it breaks.






      share|improve this answer











      $endgroup$
















        2












        2








        2





        $begingroup$

        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.



        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 somewhere in the range of



        3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C21H44}$



        . A bit more, because you can likely make the inner methyl substituents longer,



        3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C25H52}$



        , and then you can enlarge probably the nPr and Et to iBu and s-Bu that's $ce{C29H60}$. Any more and I'll bet it breaks.






        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.



        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 somewhere in the range of



        3,5-di-tert-butyl-2,2,3,4,4,5,6,6-octaamethylheptane = $ce{C21H44}$



        . A bit more, because you can likely make the inner methyl substituents longer,



        3,5-di-tert-butyl-3,5-diethyl-4,4-di-n-propyl-2,2,6,6-tetraamethylheptane = $ce{C25H52}$



        , and then you can enlarge probably the nPr and Et to iBu and s-Bu that's $ce{C29H60}$. Any more and I'll bet it breaks.







        share|improve this answer














        share|improve this answer



        share|improve this answer








        edited 1 hour ago

























        answered 2 hours ago









        KarlKarl

        5,5351329




        5,5351329






























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