What is the correct name of 3-isopropyl-4-methylhexane?

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Structure of 3-ethyl-2,4-dimethylhexane



In the branched alkane shown above, I've been told that 3-isopropyl-4-methylhexane is supposedly the correct name. However, in the alternative numbering scheme on the right, the parent chain is still of the same length (six carbon atoms) and has more substituents, so shouldn't that be the preferred name?






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    up vote
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    Structure of 3-ethyl-2,4-dimethylhexane



    In the branched alkane shown above, I've been told that 3-isopropyl-4-methylhexane is supposedly the correct name. However, in the alternative numbering scheme on the right, the parent chain is still of the same length (six carbon atoms) and has more substituents, so shouldn't that be the preferred name?






    organic-chemistry nomenclature hydrocarbons







    share|improve this question

























      up vote
      3
      down vote

      favorite









      up vote
      3
      down vote

      favorite











      Structure of 3-ethyl-2,4-dimethylhexane



      In the branched alkane shown above, I've been told that 3-isopropyl-4-methylhexane is supposedly the correct name. However, in the alternative numbering scheme on the right, the parent chain is still of the same length (six carbon atoms) and has more substituents, so shouldn't that be the preferred name?






      organic-chemistry nomenclature hydrocarbons







      share|improve this question















      Structure of 3-ethyl-2,4-dimethylhexane



      In the branched alkane shown above, I've been told that 3-isopropyl-4-methylhexane is supposedly the correct name. However, in the alternative numbering scheme on the right, the parent chain is still of the same length (six carbon atoms) and has more substituents, so shouldn't that be the preferred name?






      organic-chemistry nomenclature hydrocarbons




      organic-chemistry nomenclature hydrocarbons






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      edited 10 mins ago









      orthocresol♦

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      Hema

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          Both the names you have given are not the preferred name for the molecule above. You are correct that the preferred name maximises the number of substituents when there is a choice: see Alkane nomenclature - choosing the parent chain - maximize or minimize substituents? So, a name of the form a-ethyl-(b,c)-dimethylhexane (where a, b, and c are appropriately chosen locant numbers) is preferred over a name of the form a-isopropyl-b-methylhexane, as it has three substituents as opposed to two.



          However, the numbering on the right is not correct either. If you number the carbon chain the other way around instead, you would obtain the name 3-ethyl-2,4-dimethylhexane:



          3-Ethyl-2,4-dimethylhexane



          This is preferred over your proposed name 4-ethyl-3,5-dimethylhexane, because the locant set (2,3,4) in 3-ethyl-2,4-dimethylhexane is lower than the locant set (3,4,5) in 4-ethyl-3,5-dimethylhexane.



          Note also that according to current IUPAC nomenclature recommendations (P-57.1.1.1 of the 2013 Blue Book), the preferred prefix for $ce-CH(CH3)2$ is "propan-2-yl", not "isopropyl".






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            Both the names you have given are not the preferred name for the molecule above. You are correct that the preferred name maximises the number of substituents when there is a choice: see Alkane nomenclature - choosing the parent chain - maximize or minimize substituents? So, a name of the form a-ethyl-(b,c)-dimethylhexane (where a, b, and c are appropriately chosen locant numbers) is preferred over a name of the form a-isopropyl-b-methylhexane, as it has three substituents as opposed to two.



            However, the numbering on the right is not correct either. If you number the carbon chain the other way around instead, you would obtain the name 3-ethyl-2,4-dimethylhexane:



            3-Ethyl-2,4-dimethylhexane



            This is preferred over your proposed name 4-ethyl-3,5-dimethylhexane, because the locant set (2,3,4) in 3-ethyl-2,4-dimethylhexane is lower than the locant set (3,4,5) in 4-ethyl-3,5-dimethylhexane.



            Note also that according to current IUPAC nomenclature recommendations (P-57.1.1.1 of the 2013 Blue Book), the preferred prefix for $ce-CH(CH3)2$ is "propan-2-yl", not "isopropyl".






            share|improve this answer


























              up vote
              7
              down vote













              Both the names you have given are not the preferred name for the molecule above. You are correct that the preferred name maximises the number of substituents when there is a choice: see Alkane nomenclature - choosing the parent chain - maximize or minimize substituents? So, a name of the form a-ethyl-(b,c)-dimethylhexane (where a, b, and c are appropriately chosen locant numbers) is preferred over a name of the form a-isopropyl-b-methylhexane, as it has three substituents as opposed to two.



              However, the numbering on the right is not correct either. If you number the carbon chain the other way around instead, you would obtain the name 3-ethyl-2,4-dimethylhexane:



              3-Ethyl-2,4-dimethylhexane



              This is preferred over your proposed name 4-ethyl-3,5-dimethylhexane, because the locant set (2,3,4) in 3-ethyl-2,4-dimethylhexane is lower than the locant set (3,4,5) in 4-ethyl-3,5-dimethylhexane.



              Note also that according to current IUPAC nomenclature recommendations (P-57.1.1.1 of the 2013 Blue Book), the preferred prefix for $ce-CH(CH3)2$ is "propan-2-yl", not "isopropyl".






              share|improve this answer
























                up vote
                7
                down vote










                up vote
                7
                down vote









                Both the names you have given are not the preferred name for the molecule above. You are correct that the preferred name maximises the number of substituents when there is a choice: see Alkane nomenclature - choosing the parent chain - maximize or minimize substituents? So, a name of the form a-ethyl-(b,c)-dimethylhexane (where a, b, and c are appropriately chosen locant numbers) is preferred over a name of the form a-isopropyl-b-methylhexane, as it has three substituents as opposed to two.



                However, the numbering on the right is not correct either. If you number the carbon chain the other way around instead, you would obtain the name 3-ethyl-2,4-dimethylhexane:



                3-Ethyl-2,4-dimethylhexane



                This is preferred over your proposed name 4-ethyl-3,5-dimethylhexane, because the locant set (2,3,4) in 3-ethyl-2,4-dimethylhexane is lower than the locant set (3,4,5) in 4-ethyl-3,5-dimethylhexane.



                Note also that according to current IUPAC nomenclature recommendations (P-57.1.1.1 of the 2013 Blue Book), the preferred prefix for $ce-CH(CH3)2$ is "propan-2-yl", not "isopropyl".






                share|improve this answer














                Both the names you have given are not the preferred name for the molecule above. You are correct that the preferred name maximises the number of substituents when there is a choice: see Alkane nomenclature - choosing the parent chain - maximize or minimize substituents? So, a name of the form a-ethyl-(b,c)-dimethylhexane (where a, b, and c are appropriately chosen locant numbers) is preferred over a name of the form a-isopropyl-b-methylhexane, as it has three substituents as opposed to two.



                However, the numbering on the right is not correct either. If you number the carbon chain the other way around instead, you would obtain the name 3-ethyl-2,4-dimethylhexane:



                3-Ethyl-2,4-dimethylhexane



                This is preferred over your proposed name 4-ethyl-3,5-dimethylhexane, because the locant set (2,3,4) in 3-ethyl-2,4-dimethylhexane is lower than the locant set (3,4,5) in 4-ethyl-3,5-dimethylhexane.



                Note also that according to current IUPAC nomenclature recommendations (P-57.1.1.1 of the 2013 Blue Book), the preferred prefix for $ce-CH(CH3)2$ is "propan-2-yl", not "isopropyl".







                share|improve this answer














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                orthocresol♦

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