1. 10.1 Hydrocarbons 10.2 Aromatic Compounds 10.3 Functional Groups 10.4 Stereochemistry Chapter 10. Organic Chemistry - Structure Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

2. 10.1 Hydrocarbons Learning objective: Draw and naming hydrocarbons using the IUPAC system Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

3. 10.1 Hydrocarbons Alkanes  C n H 2n+2  saturated (single C-C bonds only)  methane, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

4. Alkanes Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

5. Alkane Isomers Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd. Isobutane Butane PentaneIsopentaneNeopentane

6. Alkyl Groups Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

7. Naming Branched-Chain Alkanes Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd. 1. Locate the longest continuous chain of carbon atoms. 2. Number the longest chain beginning with the end nearest the substituent. 3. Number the substituent groups accordingly.

8. Naming Branched-Chain Alkanes Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

9. Example 10 – 1 Naming Alkanes Name the following alkanes: Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

10. Example 10 – 2 Drawing Alkanes Draw line structures of the following alkanes: (a) 2,3,6- trimethyloctane; (b) 5-ethyl-2-methyl-5-propylnonane; and (c) 2-methylbutane. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

11. Cycloalkanes Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

12. Common Substituents Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

13. Alkenes  C n H 2n  Unsaturated (contain at least one C-C double bond)  ethene, propene, butene, … Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

14. Alkynes  C n H 2n-2  Unsaturated (contain at least one C-C triple bond)  ethyne, propyne, butyne, … Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

15. Naming Alkenes and Alkynes Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

16. 10.2 Aromatic Compounds Learning objective: Draw and name aromatic compounds using the IUPAC system Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

17. Structure of Benzene Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

18.  Bonding in Benzene Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

19. Naming Benzene Compounds Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

20. Example 10-3 Naming Benzene Compounds Name the following compounds: Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

21. 10.3 Functional Groups Learning objective: Drawing and naming compounds containing common functional groups. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

22. Functional Groups Alkyl Halides Alcohols Ethers Amines Aldehydes Ketones Carboxylic Acids Esters Amides Nitriles Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

23. Alkyl Halides Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

24. Example 10 – 4 Alkyl Halides Draw line structures and give the IUPAC names for all of the structural isomers of C 4 H 9 Br. State whether each is a primary, secondary, or tertiary alkyl halide. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

25. Alcohols Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd. Alcohols H-bond, as does water

26. Primary Alcohols Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

27. Secondary Alcohols Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

28. Tertiary Alcohols Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

29. Naming Alcohols Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

30. Synthesizing Alcohols Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd. PropeneIsopropanol

31. Example 10 – 5 Alcohols Write line structures for each of the following, and state whether each is a primary, secondary, or tertiary alcohol: (a) 3-pentanol; (b) 2-methyl-2-butanol; and (c) 1-hexanol. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

32. Ethers Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

33. Example 10 – 6 Ethers Write line structures for (a) diethyl ether, (b) ethyl propyl ether, and (c) ethyl isopropyl ether. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

34. Amines Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

35. Amines Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

36. Example 10 – 7 Amines Name the following amines and classify each as primary, secondary, or tertiary: Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

37. The Carbonyl Group Appears in five common functional groups: Aldehydes, Ketones, Carboxylic Acids, Esters and Amides Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

38. Aldehydes and Ketones Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

39. Aldehydes and Ketones Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

40. Example 10 – 8 Aldehydes and Ketones Give IUPAC names for the following compounds: Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

41. Carboxylic Acids Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

42. Carboxylic Acids Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

43. Carboxylic Acids Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

44. Esters Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

45. Amides Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

46. Example 10 – 9 Carboxylic Acids, Esters, and Amides Draw the following compounds: (a) hexanoic acid; (b) 2- ethyl butanoic acid; (c) methyl propanoate, (d) phenyl ethanoate; (e) N-ethylethanamide (N-ethylacetamide); and (f) N-methyl-N-phenylpropanamide. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

47. Nitriles Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

48. Functional Group Summary Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

49. Functional Group Summary – cont’d Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

50. 10.4 Stereochemistry Learning objective: Recognizing, naming and drawing stereoisomers. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

51. 10.4 Stereochemistry Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd. These are different molecules!

52. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd. 1. List the groups bound directly to the C=C double bond. In this case, they are –H, -Br, -Cl and –CH 3. 2. Order them according to priority (higher molecular weight = higher priority) on each C atom. Here, Br > Cl and CH 3 > H. 3. Look at the highest priority ones (Br, CH 3 ). If they are cis to one another, it is Z. If they are trans, it is E. This one is therefore (E)-1-bromo-1- chloropropene The E/Z System

53. Example 10 – 10 E/Z Stereoisomers Draw and name the two stereoisomers of 1-bromo-3- chloro-4-isopropyl-3-heptene. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

54. Learn to Draw in Three Dimensions! Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

55. Conformations Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

56. Drawing a Newman Projection Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

57. Example 10-11 Drawing Newman Projections Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

58. Example 10-12 Drawing a Line Structure from a Newman Projection Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

59. Potential Energy During a Rotation Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

60. Enantiomers Your hands are enantiomers – non-superimposable mirror images of one another Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

61. Chirality 2-pentanol These are therefore enantiomers! Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

62. Chirality Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

63. Example 10 – 13 Chiral Compounds Two amino acids are glycine and leucine. Determine whether each of these compounds is chiral or achiral. Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

64. The R/S System for Naming Chiral Compounds Chirality may determine the activity of a molecule! Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

65. The R/S System Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd. 1. Locate the chirality centre, identify the four groups attached to it, and assign priorities to them just as we did for the E/Z configurations of cis–trans stereoisomers. 2. Orient the molecule so that the group having the lowest priority is pointing away from you. 3. Read the other three groups (pointing toward you) from highest to lowest priority. If these are in a clockwise direction, the molecule is the R enantiomer. If they are in the counter-clockwise direction, it is the S enantiomer.

66. The R/S System Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd. The groups attached to the chirality centre in increasing priority are - H, -CH 3, -C 6 H 4 and COOH. The other three groups from highest to lowest priority are - COOH, -C 6 H 4 and -CH 3. These three groups are in a clockwise order, and so this is the (R)- ibuprofen, and the active enantiomer must be (S)-ibuprofen. The inactive enantiomer of Ibuprofen

67. Example 10 – 14 Identifying R and S Enantiomers Assign an R or S configuration to the chirality centre in the enantiomer of 3,3-dimethylcyclohexanol shown: Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

68. Chapter 10 Visual Summary Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

69. Chapter 10 Visual Summary Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

70. Chapter 10 Visual Summary Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.

71. Chapter 10 Visual Summary Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.