1. 1 Organic Chemistry Chapter 20

2. 2 Carbon All living matter Four bonds Double and triple bonds

3. 3 Diamond Colorless crystalline solid Extremely high melting point Conducts heat very well Does not conduct electricity Covalent network bonding Bonded to four nearest neighbors

4. 4 Graphite Crumbles easily Feels greasy Atoms arranged in thin layers Weak London dispersion forces Layers slide past each other Conducts electricity

5. 5 Fullerenes Formed when carbon-containing materials are burned with limited oxygen Nearly spherical C 60 Most stable Called buckminsterfullerene or buckyball

6. 6

7. 7 Organic compounds Covalently bonded compounds containing carbon Except: Carbonates and oxides

8. 8 Catenation Covalent bonding of an element to itself to form chains or rings Carbon can also double or triple bond to itself

9. 9 hydrocarbons Contain only carbon and hydrogen Simplest organic compounds

10. 10 Structural formula Regular or condensed Carbon makes four bonds, hydrogen makes one Hydrogen is understood to bond to the atom next to it

11. 11 Draw the condensed structural formulas

12. 12 Geometric isomers Order of atom bonding is the same, but arrangement of atoms is space is different Need rigid structure in molecule Double or triple bond Need two carbons each with two different groups attached Cis and trans isomers

13. 13 Cis isomer Like groups on same side of carbon atoms

14. 14 Trans iosmer Like groups on opposite sides of carbon atoms

15. 15 Alkanes AKA saturated hydrocarbons Hold maximum amount of hydrogen Contain only single bonds General formula C n H 2n+2

16. 16 Cycloalkanes Carbons arranged in ring Fewer hydrogen atoms – no free ends General formula C n H 2n

17. 17 propane vs. cyclopropane

18. 18 Simplified cycloalkane structure Carbon at each corner Enough hydrogen so each carbon has four bonds

19. 19 IUPAC International Union of Pure and Applied Chemistry Systematic naming system

20. 20 Unbranched chain alkanes Count carbon atoms for prefix Table 20-3, page 636 And suffix -ane

21. 21 You try

22. 22 Branched-chain alkanes Branches are alkyl groups Table 20-4, page 637

23. 23 Alkane nomenclature 1. Name the parent hydrocarbon Longest continuous carbon chain Might be bent Name as straight-chain alkane

24. 24

25. 25 Alkane nomenclature 2. Add the names of the alkyl groups In front alphabetize Add prefixes if necessary (di-, tri-, tetra-, penta-, etc.)

26. 26

27. 27 Alkane nomenclature 3. Number the carbon atoms in parent alkane Give lowest numbers to alkyl groups If two possibilities, make the first alkyl group in name have lowest number 4. Insert position numbers Before alkyl group names

28. 28

29. 29 Alkane nomenclature 5. Punctuate Hyphens between numbers and names Commas between numbers

30. 30

31. 31 You try Name the molecule above octane

32. 32 You try Name the molecule above 3-ethyl-2,4,5-trimethyloctane

33. 33 You try Name the molecule above 5-butyl-2,2-dimethylnonane

34. 34 Example Draw the condensed structural formula for 3,3,4- triethyl-4-methylhexane.

35. 35 You try Draw the condensed structural formula for 3- ethyl-2,2-dimethylpentane.

36. 36 Alkenes Unsaturated hydrocarbons Have at least one double bond

37. 37 Alkene nomenclature 1. Name the parent hydrocarbon Longest continuous carbon chain containing double bond Might be bent Add suffix –ene if only one double bond If two, -adiene Three, - atriene Etc.

38. 38 Alkene nomenclature 2. Add the names of the alkyl groups 3. Number the carbon atoms in parent alkene First carbon in double bond nearest end of chain has lowest number If two possibilities, number from end nearest first alkyl groups

39. 39 Alkene nomenclature 4. Insert position numbers Double-bond position numbers before parent alkene name Before alkyl group names 5. Punctuate

40. 40 Example Name the following alkene.

41. 41 You try Name the following alkene

42. 42 You try Draw 1,3-butadiene

43. 43 Alkynes Contain at least one triple covalent bond.

44. 44 Alkyne nomenclature 1. Name the parent hydrocarbon Longest continuous carbon chain containing triple bond Might be bent Add suffix –yne if only one triple bond If two, -adiyne Three, - atriyne Etc.

45. 45 Alkyne nomenclature 2. Add the names of the alkyl groups 3. Number the carbon atoms in parent alkyne. First carbon in triple bond nearest end of chain has lowest number If two possibilities, number from end nearest first alkyl groups

46. 46 Alkyne nomenclature 4. Insert position numbers Triple-bond position numbers before parent alkyne name Before alkyl group names 5. Punctuate

47. 47 You try Name the following compound

48. 48 You try Draw 3,3-dimethyl-1-butyne

49. 49 Aromatic hydrocarbons Contain six-membered benzene ring Delocalized electrons

50. 50 Aromatic hydrocarbon nomenclature 1. Name the parent hydrocarbon Benzene 2. Add the names of the alkyl groups 3. Number the carbon atoms in ring 1 goes with alkyl group that comes first alphabetically Number in the direction that gives the rest of the groups the lowest numbers

51. 51 Aromatic hydrocarbon nomenclature 4. Insert position numbers 5. Punctuate

52. 52 You try Name the following compound

53. 53 You try Draw 1-ethyl-2-methylbenzene