2. The study of carbon-based compounds and their properties.

6. Historically the distinction between inorganic and organic substances was based on whether or not they were produced by living systems. It was believed that some sort of “life force” was needed to synthesize them.

7. In 1828, the German chemist Freidrich Wohler (1800-1882) prepared urea from the inorganic salt ammonium cyanate by simple heating. NH 4 OCN  H 2 N—C—NH 2 O urea

8. Hydrocarbons: contain only hydrogen and carbon Hydrocarbons AliphaticAromatic AlkanesAlkenesAlkynesCyclic Hydrocarbons can be divided into different types, depending on their bonding.

9. Naming Organic Molecules Alkanes - - Carbon chain, no double or triple bonds. All single bonds (saturated) Alkenes - - Carbon chain, contains double bond(s) (unsaturated) Alkynes - - Carbon chain, contains triple bond(s) (unsaturated)

10. Naming Organic Molecules There are two parts to the main name of each molecule… prefix: tells the # of carbons in main chain or ring suffix: tells the type of bonding in the chain or ring

11. Prefix: indicates number of carbon atoms in the main chain or ring 1meth- 2eth- 3prop- 4but- 5pent- 6hex- 7hept- 8oct- 9non- 10dec-

12. Suffix Explained….  The chemical suffix or end part of a chemical name needs careful attention.  There is a big difference between the "ide", "ate" and "ite" suffixes.  1. As a general rule an "ide" suffix indicates an element. eg. sulfide S 2-, nitride N 3- and phosphide P 3-  The exceptions are hydroxide OH - and cyanide CN -  2. "ates" and "ites" always contain oxygen. eg. nitrate NO 3 - and nitrite NO 2 -  3. "ates" always have a higher number of oxygen atoms the corresponding "ites". eg. sulfate SO 4 2- and sulfite SO 3 2-

13. Suffix: indicates types of bonds present Alkanes: (all single bonds) ___ -ane Alkenes: (double bond) ___ -ene Alkyne: (triple bond) ___ -yne

14. Saturated Hydrocarbons:  the ALKANES: chains of carbon connected by single bonds: contain only single C-C bonds

15. Saturated v. Unsaturated fats Saturated with H Single bonds are free to rotate, so these fats can pack tightly (solid @ room temp)

16. Which one is saturated?

17. For a bit of a demonstration…  Good Eats fat train analogyfat train analogy Watch episode from 1:30 to 5:00

18. ALKANES

20. ALKANES propane, C 3 H 8

21. ALKANES butane, C 4 H 10

22. ALKANES pentane, C 5 H 12

23. ALKANES hexane, C 6 H 14

24. ALKANES octane, C 8 H 18

25. Don’t write this example down, but watch to see where we’re going with this…

29. “Normal” v. Branched  “normal” hydrocarbons are straight chains; no branching  Branched-chain hydrocarbons – isomers of “normal” hydrocarbons; have same formula, but different structures

30. Timberlake LecturePLUS29 Alkanes Contain C and H only Contain single bonds C-C Have 4 bonds to every carbon (C) atom Are nonpolar

31. Timberlake LecturePLUS30 Complete Structural Formulas Show the bonds between each of the atoms H H  H  C  HH C H  H H CH 4, methane

32. Timberlake LecturePLUS31 More Alkanes H HCondensed Structural Formulas H C C HCH 3 CH 3 H HEthane H H H H C C C HCH 3 CH 2 CH 3 H H H Propane

33. Timberlake LecturePLUS32 IUPAC Names Name# carbons Structural Formula Methane1CH 4 Ethane2CH 3 CH 3 Propane3CH 3 CH 2 CH 3 Butane4CH 3 CH 2 CH 2 CH 3 Pentane5CH 3 CH 2 CH 2 CH 2 CH 3

34. Timberlake LecturePLUS33 IUPAC NAMES Name # carbons Structural Formula Hexane 6 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 Heptane 7 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Octane 8 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Nonane 9 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Decane 10 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3

35. Timberlake LecturePLUS34 Learning Check Alk1 A. What is the condensed formula for H H H H H C C C C H H H H H B. What is its molecular formula? C. What is its name?

36. Timberlake LecturePLUS35 Solution Alk1 A.CH 3 CH 2 CH 2 CH 3 B. C 4 H 10 C.butane

37. n-butane

38. Naming side chains Root is the longest possible HC chain Must contain multiple bonds if present Add -yl to get name of side chain Common side chains include: CH 3 - methyl CH 3 CH 2 - ethyl CH 3 CH 2 CH 2 - propyl (CH 3 ) 2 CH- isopropyl Br- (bromo) Cl- (chloro) F- (fluoro) I- (iodo)  Give 1 st bond (1 st point of difference) lowest #  include di, tri, tetra, penta, etc. before ene/yne  Comma between #s, hyphen between #-letter

39. 2-methylpropane

40. n-pentane

41. 2-methylbutane

42. Another branched alkane: 2,2-dimethylpentane

43. Naming side chains Example: name the following structure Step 1 - choose the correct ending

44. Naming side chains Step 2 - find the longest chain

45. Naming side chains Step 3 - add the prefix naming the longest chain

46. Naming side chains Step 4 - number the longest chain with the lowest number closest to the double bond

47. Naming side chains Step 5 - add that number to the name

48. Naming side chains ethyl methyl Step 6 - Name the side chains

49. Naming side chains ethyl methyl Step 7 - Place the side chains in alphabetical order & name the compound

50. Name

51. Draw the structures below 3-ethyl-2-methylpentane 3-ethyl-1,5,5-trimethylcyclohexene

52. More practice

53. 2,2-dimethyl-3-hexene 2,5-dimethyloctane octane 1,3-diethylcyclopentane 1 2 3 4

54. cyclopentane Cycloalkanes

55.  cyclobutane

56. Cycloalkanes  ________________________ methyl- ethyl- 1 2 3 3 2 1 green or red? -ethyl- -methylcyclopentane13

57. Unsaturated Hydrocarbons: ALKENES – contain C-C double bonds 2-pentene

58. Unsaturated Hydrocarbons: ALKENES – contain C-C double bonds 2,4-hexadiene

59. Unsaturated Hydrocarbons: ALKYNES – contain C-C triple bonds 1-butyne

60. Unsaturated Hydrocarbons: ALKYNES – contain C-C triple bonds 3-ethyl-1-pentyne

61. Numbering carbons Draw 1-pentene Name these C2H4C2H4

62. Aromatic Hydrocarbons: benzene – the simplest aromatic hydrocarbon; has a symmetrical ring structure

63. Aromatic Hydrocarbons: benzene – can be drawn like this…

64. Derivatives of benzene: 1-ethyl-2-methylbenzene

65. Derivatives of benzene: 1-propyl,3,4-dimethylbenzene

66. For your homework: If a halogen is attached, use the following prefixes: fluoro- chloro- bromo- iodo- (instead of methyl-, ethyl-, propyl-, etc.)

67. Multiple multiple bonds – Practice CH 3 CH 2 CH 2 CH=C=CH 2

68. 3,3-dimethyl,1-cyclopentene cyclopropane 4-nonene 6-ethyl-2-octyne 5 6 7 8

69. cyclobutene 1,2-dimethyl-6-propylcyclodecane benzene 3,4-diethyl-2-hexene 1213 14 15

70. 4-ethyl-1,2-dimethylcycloheptane 2-hexene 2,7,8-trimethyldecane 3,3-diethylpentane 16 17 18 19

71. 3-ethyl-2-methylpentane 3-ethyl-1,5,5-trimethylcyclohexene 20 21