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Drawing Cyclohexane and Decalins

Drawing Cyclohexane and Decalins. parallel bonds. parallel bonds. parallel bonds. Drawing Cyclohexane. equatorial bonds. axial bonds. equatorial bonds. axial bonds. Numbering Cyclohexane. 4. 6. 5. 1. 3. 2. Start anywhere and number consecutive carbons. Tetrahedral Carbons in

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Drawing Cyclohexane and Decalins

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  1. Drawing Cyclohexane and Decalins

  2. parallel bonds parallel bonds parallel bonds Drawing Cyclohexane

  3. equatorial bonds

  4. axial bonds

  5. equatorial bonds axial bonds

  6. Numbering Cyclohexane

  7. 4 6 5 1 3 2 Start anywhere and number consecutive carbons.

  8. Tetrahedral Carbons in Cyclohexane

  9. 1 tetrahedral carbon

  10. 2 tetrahedral carbon

  11. 3 tetrahedral carbon

  12. 4 tetrahedral carbon

  13. 5 tetrahedral carbon

  14. 6 tetrahedral carbon

  15. 4 6 5 1 3 2

  16. Disubstituted Isomers of Cyclohexane

  17. 1 2 trans-1,2-diequatorial

  18. and...

  19. 1 2 trans-1,2-diaxial

  20. are conformational isomers of one another, and...

  21. 1 3 cis-1,3-diequatorial

  22. and...

  23. 1 3 cis-1,3-diaxial

  24. are conformational isomers of one another, and...

  25. 4 1 trans-1,4-diequatorial

  26. and...

  27. 1 4 trans-1,4-diaxial

  28. are conformational isomers of one another.

  29. Chair Conformations of Cyclohexane

  30. hold red bonds in a plane flip this carbon above the plane flip the other carbon below the plane the other chair conformation you get

  31. number carbons in this conformation 6 4 5 2 3 1 5 number the same carbons in this conformation 6 1 3 4 2

  32. 6 4 5 C4 is above the plane, while... 2 3 1 C4 is below the plane. 5 6 C1 is below the plane and ... 1 3 4 C1 is above the plane and... 2 given the plane formed by carbons 2, 3, 5, and 6

  33. 6 4 equatorial bonds here. 5 axial bonds here become ... 2 3 1 5 1 axial bonds here, and... 6 equatorial bonds here become ... 3 4 2

  34. 4 6 5 1 3 2 above below below below above above Equatorial bonds alternate being above and below the axial bonds on a given carbon atom

  35. and...

  36. 4 6 5 1 3 2 above above above below below below axial bonds alternate being above and below the equatorial bonds on a given carbon atom.

  37. Drawing Decalins

  38. B A Start with a chair cyclohexane Add two vicinal equatorial bonds Complete a second chair cyclohexane Axial fusion bonds are diaxial to rings A and B. trans - Decalins

  39. Y Start with a chair cyclohexane Add two vicinal bonds: One equatorial; one axial A B Complete a 2nd chair cyclohexane X Ring fusion substituents are cis to rings A and B. cis-Decalin 1 Substituent X is equatorial to ring A and axial to ring B while substituent Y is equatorial to ring B and axial to ring A. cis - Decalins

  40. Start with a chair cyclohexane X Add two vicinal bonds: One axial; one equatorial A Complete a 2nd chair cyclohexane Y Ring fusion substituents are cis to rings A and B. B cis-Decalin Conformation 2 Substituent X is now axial to ring A and equatorial to ring B while substituent Y is now axial to ring B and equatorial to ring A. cis - Decalins

  41. Y cis - Decalin Conformation 1 X cis - Decalin Conformation 2 rotate clockwise 90o X X Y Y Enantiomers but equal in energy cis - Decalins

  42. The End

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