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Cycloalkanes and bicyclic alkanes

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  • Natural gas is usually a mixture of small alkanes with low boiling points (methane, ethane, and propane). Crude oil, on the other hand, contains alkanes of all sizes that are then separated through a process called “fractional distillation,” during which compounds are separated by their boiling points.
  • Natural gas is usually a mixture of small alkanes with low boiling points (methane, ethane, and propane). Crude oil, on the other hand, contains alkanes of all sizes that are then separated through a process called “fractional distillation,” during which compounds are separated by their boiling points.
  • Natural gas is usually a mixture of small alkanes with low boiling points (methane, ethane, and propane). Crude oil, on the other hand, contains alkanes of all sizes that are then separated through a process called “fractional distillation,” during which compounds are separated by their boiling points.
  • Natural gas is usually a mixture of small alkanes with low boiling points (methane, ethane, and propane). Crude oil, on the other hand, contains alkanes of all sizes that are then separated through a process called “fractional distillation,” during which compounds are separated by their boiling points.
  • Natural gas is usually a mixture of small alkanes with low boiling points (methane, ethane, and propane). Crude oil, on the other hand, contains alkanes of all sizes that are then separated through a process called “fractional distillation,” during which compounds are separated by their boiling points.
  • Not 1,3,3 – not the lowest.
  • Alphabetical order and it has more substituents.
  • Spirocyclic– are relatively rare.
  • 1st path = 4 carbons2nd path = 2 carbons3rd path = 0 carbon
  • 1st path = 3 carbons2nd path = 2 carbons3rd path = 1 carbon
  • where x, y, and z are the numbers of intervening carbons on the three paths between the two bridgehead carbons cited in decreasing numerical order, and alk refers to the total number of carbons in the ring systems
  • where x, y, and z are the numbers of intervening carbons on the three paths between the two bridgehead carbons cited in decreasing numerical order, and alk refers to the total number of carbons in the ring systems
  • Number shortest path first after spiro carbon
  • Transcript

    • 1. Cycloalkanes and Bicyclic Alkanes
    • 2. Cycloalkanes • alkanes in which the two ends of the carbon chain are connected to one another. • are named like acyclic alkanes, with the prefix cyclo- indicating the presence of a ring. • formula of a cycloalkane is CnH2n
    • 3. Cycloalkanes • resemble the acyclic, open-chain alkanes in their physical properties and in their chemistry. • nonpolar, relatively inert compounds with boiling points and melting points that depend on their molecular weights
    • 4. Cycloalkane Nomenclature The name of the compound is based on the name of the parent alkane, with “cyclo” added to the front to show that the main chain forms a ring.
    • 5. Cycloalkane Nomenclature Cyclobutane (C4H8) Cyclohexane (C6H12)
    • 6. Cycloalkane Nomenclature Substituted cycloalkanes use the cycloalkane for the base name, with the alkyl groups named as substituents. If there is just one substituent, no numbering is needed.
    • 7. Cycloalkane Nomenclature propylcyclohexane tert-butylcycloheptane
    • 8. Cycloalkane Nomenclature • If there are two groups on the ring, rank them in alphabetical order. • The carbon bearing the group first in the alphabet will be given the number “1,” and the rest of the carbons in the ring will be numbered in a way that results in the lowest possible number for the other substituent.
    • 9. Cycloalkane Nomenclature 1,1,3- trimethylcyclopentane
    • 10. Cycloalkane Nomenclature When the numbering could begin with either of two substituted ring carbons (as in a disubstituted cycloalkane), begin with the one that has more substituents, or else the one that is alphabetically first.
    • 11. Cycloalkane Nomenclature 1,1-diethyl-4-isopropylcyclohexane
    • 12. Cycloalkane Nomenclature When the acyclic portion of the molecule contains more carbon atoms than the cyclic portion, the cyclic portion is sometimes named as a cycloalkyl substituent.
    • 13. Cycloalkane Nomenclature 4-cyclopropyl-3-methyloctane
    • 14. Cycloalkane Nomenclature cyclopentylcyclohexane
    • 15. Identify! (1,2-dimethylpropyl)cyclohexane
    • 16. Identify! 3-cyclopropyl-1,1-dimethylcyclohexane
    • 17. Bicyclic Alkanes • Two or more cycloalkanes joined together • Can either be fused rings, bridged rings, or spirocyclic compounds • found in many natural product structures
    • 18. Technically bicyclic, but needs no special nomenclature rules because the rings do not share any carbon atom. cyclopentylcyclohexane
    • 19. Bicyclic Alkane Nomenclature • Fused rings are most common, sharing two adjacent carbon atoms and the bond between them. • Bridged rings are also common, sharing two nonadjacent carbon atoms (the bridgehead carbons) and one or more carbon atoms (the bridge) between them. • Spirocyclic compounds, in which the two rings share only one carbon atom. (Rare)
    • 20. Fused Bicyclic Shared Carbon Atoms = Bridgehead Carbons
    • 21. Bridged Bicyclic Shared Carbon Atoms = Bridgehead Carbons Carbon atom in between = Bridge Carbon
    • 22. Spirocyclic Alkanes Shared Carbon Atom = Spiro Carbon
    • 23. Summary
    • 24. Bicyclic Alkane Nomenclature • When the two rings of the bicyclic compound have two carbons common there are three different paths between the two common carbons following C-C bonds.
    • 25. Bicyclic Alkane Nomenclature • When the two rings of the bicyclic compound have two carbons common there are three different paths between the two common carbons following C-C bonds.
    • 26. Rules for numbering the rings in bicyclic alkanes 1. Start with one of the bridgehead carbons and number it 1.
    • 27. Rules for numbering the rings in bicyclic alkanes 2. Proceed round the longest chain of carbons to the second bridgehead.
    • 28. Rules for numbering the rings in bicyclic alkanes 3. Number the second bridgehead carbon and continue on round the next longest chain of carbons back towards the first bridgehead carbon.
    • 29. Rules for numbering the rings in bicyclic alkanes 4. Pass over the first bridgehead carbon (it already has the number 1) and along the shortest chain of carbons to the second bridgehead carbon again.
    • 30. Bicyclic Alkane Nomenclature • The generic name for bicyclic (fused and bridges) alkanes is: bicyclo[x.y.z]alkane • where x, y, and z are the numbers of intervening carbons on the three paths between the two bridgehead carbons cited in decreasing numerical order • alk refers to the total number of carbons in the ring systems
    • 31. Bicyclic Alkane Nomenclature Bicyclo[4.2.0]octane
    • 32. Bicyclic Alkane Nomenclature Bicyclo[5.3.0]decane
    • 33. Bicyclic Alkane Nomenclature Bicyclo[2.2.1]heptane
    • 34. Bicyclic Alkane Nomenclature Bicyclo[2.2.2]octane
    • 35. Bicyclic Alkane Nomenclature 7,7-dimethylbicyclo[2.2.1]heptane 7 1 2 3 4 5 6
    • 36. Spirocyclic Alkane Nomenclature spiro[x.y]alkane • where x and y are the numbers of intervening carbons on the two paths between the spiro carbon. • Shortest path named first! • Numbering begins at carbon in the shortest path nearest to the spiro carbon. • alk refers to the total number of carbons in the ring systems
    • 37. Spirocyclic Alkane Nomenclature spiro[3.4]octane
    • 38. Spirocyclic Alkane Nomenclature Spiro[4.5]decane