1. © 2012 Pearson Education, Inc. Conceptual Physical Science 5 th Edition Chapter 19: ORGANIC COMPOUNDS © 2012 Pearson Education, Inc.

2. This lecture will help you understand: Hydrocarbons Unsaturated Hydrocarbons Functional Groups Alcohols, Phenols, and Ethers Amines and Alkaloids Carbonyl Compounds Polymers

3. © 2012 Pearson Education, Inc. Organic Chemistry A branch of chemistry involving the study of carbon-containing chemical compounds.

4. © 2012 Pearson Education, Inc. 100,000 new ones each year Organic Chemistry Organic Compound: A carbon containing chemical compound natural synthetic Over 13 million known!

5. © 2012 Pearson Education, Inc. Organic Chemistry Why is carbon so special?

6. © 2012 Pearson Education, Inc. Organic Chemistry Why is carbon so special? Carbon atoms connect with one another through strong and stable covalent bonds.

7. © 2012 Pearson Education, Inc. Organic Chemistry CCC C C C NNN N N N OOO O O O SS S SS

8. © 2012 Pearson Education, Inc. Organic Chemistry CCC C C C NNN N N N OOO O O O SS S SS 347 kJ/mol

9. © 2012 Pearson Education, Inc. Organic Chemistry CCC C C C NNN N N N OOO O O O SS S SS 347 kJ/mol 159 kJ/mol

10. © 2012 Pearson Education, Inc. Organic Chemistry CCC C C C NNN N N N OOO O O O SS S SS 347 kJ/mol 159 kJ/mol 138 kJ/mol

11. © 2012 Pearson Education, Inc. Organic Chemistry CCC C C C NNN N N N OOO O O O SS S SS 347 kJ/mol 159 kJ/mol 138 kJ/mol 226 kJ/mol

12. © 2012 Pearson Education, Inc. Organic Chemistry S S S S S S S S Sulfur, S 8

13. © 2012 Pearson Education, Inc. Organic Chemistry S S S S S S S S Sulfur, S 8 More atoms of the same element bound together like this is rare…

14. © 2012 Pearson Education, Inc. Organic Chemistry S S S S S S S S Sulfur, S 8 More atoms of the same element bound together like this is rare… …for every element except carbon….

15. © 2012 Pearson Education, Inc. C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C Diamond

16. © 2012 Pearson Education, Inc. Organic Chemistry Why is carbon so special? Carbon atoms connect with one another through strong and stable covalent bonds. Carbon atoms also readily form bonds with many other types of atoms. This provides for a near infinite number of different kinds of organic compounds.

17. © 2012 Pearson Education, Inc. Organic Chemistry To appreciate organic chemistry, please minimize memorization…

18. © 2012 Pearson Education, Inc. Hydrocarbons Hydrocarbon: A chemical compound containing only hydrogen and carbon.

19. © 2012 Pearson Education, Inc. Hydrocarbons

20. © 2012 Pearson Education, Inc. Hydrocarbons Structural isomer: Molecules having the same molecular formula but different structures.

21. © 2012 Pearson Education, Inc. Hydrocarbons Structural isomer: Molecules having the same molecular formula but different structures.

22. © 2012 Pearson Education, Inc. Hydrocarbons Structural isomer: Molecules having the same molecular formula but different structures. “configurations”

23. © 2012 Pearson Education, Inc. Hydrocarbons Structural isomer: Molecules having the same molecular formula but different configurations. Configuration: The specific way in which the atoms of a molecule are connected to one another.

24. © 2012 Pearson Education, Inc. Hydrocarbons Structural isomer: Molecules having the same molecular formula but different configurations. Configuration: The specific way in which the atoms of a molecule are connected to one another. “Configuration” = “Connectivity”

25. © 2012 Pearson Education, Inc. C 7 H 16 C 8 H 18 C 10 H 22 C 20 H 42 C 6 H 14 C 5 H 12 9 18 75 366,319 5 3 Formula Number of possible isomers

26. © 2012 Pearson Education, Inc. Hydrocarbons Conformation: The spatial orientation of a single configuration.

27. © 2012 Pearson Education, Inc. Hydrocarbons Conformation: The spatial orientation of a single configuration. Rotate this bond

28. © 2012 Pearson Education, Inc. Hydrocarbons Conformation: The spatial orientation of a single configuration.

29. © 2012 Pearson Education, Inc. Hydrocarbons Conformation: The spatial orientation of a single configuration. Like pivoting your arm at the elbow

30. © 2012 Pearson Education, Inc. Hydrocarbons Conformation: The spatial orientation of a single configuration. These are two “conformations” of the same configuration.

31. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 3 H 8 B.C 4 H 10 C.C 5 H 12 D.C 6 H 14 Hydrocarbons CHECK YOUR NEIGHBOR

32. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 3 H 8 B.C 4 H 10 C.C 5 H 12 D.C 6 H 14 Hydrocarbons CHECK YOUR ANSWER

33. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 3 H 8 B.C 4 H 10 C.C 5 H 12 D.C 6 H 14 c c c c c Hydrocarbons CHECK YOUR ANSWER

34. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 3 H 8 B.C 4 H 10 C.C 5 H 12 D.C 6 H 14 c c c c c H H H HH H H H H H H H Hydrocarbons CHECK YOUR ANSWER

35. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 3 H 8 B.C 4 H 10 C.C 5 H 12 D.C 6 H 14 c c c c c H H H HH H H H H H H H Hydrocarbons CHECK YOUR ANSWER

36. © 2012 Pearson Education, Inc. Hydrocarbons

37. © 2012 Pearson Education, Inc. Unsaturated Hydrocarbons Carbon always forms four bonds.

38. © 2012 Pearson Education, Inc. Unsaturated Hydrocarbons Carbon always forms four bonds.

39. © 2012 Pearson Education, Inc. Unsaturated Hydrocarbons Carbon always forms four bonds. Some of these bonds, however, may be within multiple bonds.

40. © 2012 Pearson Education, Inc. Unsaturated Hydrocarbons Carbon always forms four bonds. Some of these bonds, however, may be within multiple bonds.

41. © 2012 Pearson Education, Inc. Unsaturated Hydrocarbons Unsaturated Hydrocarbon: A hydrocarbon containing one or more multiple bonds.

42. © 2012 Pearson Education, Inc. Unsaturated Hydrocarbons Unsaturated Hydrocarbon: A hydrocarbon containing one or more multiple bonds. A special case of an unsaturated hydrocarbon is the benzene ring.

43. © 2012 Pearson Education, Inc. Unsaturated Hydrocarbons Unsaturated Hydrocarbon: A hydrocarbon containing one or more multiple bonds. A special case of an unsaturated hydrocarbon is the benzene ring.

44. © 2012 Pearson Education, Inc. Unsaturated Hydrocarbons Unsaturated Hydrocarbon: A hydrocarbon containing one or more multiple bonds. A special case of an unsaturated hydrocarbon is the benzene ring.

45. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 5 H 10 B.C 5 H 12 C.C 6 H 12 D.C 6 H 14 Unsaturated Hydrocarbons CHECK YOUR NEIGHBOR

46. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 5 H 10 B.C 5 H 12 C.C 6 H 12 D.C 6 H 14 Unsaturated Hydrocarbons CHECK YOUR ANSWER

47. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 5 H 10 B.C 5 H 12 C.C 6 H 12 D.C 6 H 14 c c c c c Unsaturated Hydrocarbons CHECK YOUR ANSWER

48. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 5 H 10 B.C 5 H 12 C.C 6 H 12 D.C 6 H 14 c c c c c H H H HH H H H H H Unsaturated Hydrocarbons CHECK YOUR ANSWER

49. © 2012 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 5 H 10 B.C 5 H 12 C.C 6 H 12 D.C 6 H 14 c c c c c H H H HH H H H H H Unsaturated Hydrocarbons CHECK YOUR ANSWER

50. © 2012 Pearson Education, Inc. Functional Groups Heteroatom:Any atom other than hydrogen or carbon in an organic molecule.

51. © 2012 Pearson Education, Inc. Functional Groups Heteroatom:Any atom other than hydrogen or carbon in an organic molecule. Functional Group: A combination of carbon, hydrogen, and heteroatoms that behave as a single unit.

52. © 2012 Pearson Education, Inc. Functional Groups Heteroatom:Any atom other than hydrogen or carbon in an organic molecule. Functional Group: A combination of carbon, hydrogen, and heteroatoms that behave as a single unit. Organic molecules are classified by the functional groups they contain.

53. © 2012 Pearson Education, Inc. Functional Groups Heteroatom:Any atom other than hydrogen or carbon in an organic molecule. Functional Group: A combination of carbon, hydrogen, and heteroatoms that behave as a single unit. Organic molecules are classified by the functional groups they contain. For example…

54. © 2012 Pearson Education, Inc. Functional Groups

55. © 2012 Pearson Education, Inc. In which of the following structures is carbon bonded five times? A.B.C.D. Functional Groups CHECK YOUR NEIGHBOR

56. © 2012 Pearson Education, Inc. A.B.C.D. Explanation: Carbon can never be bonded five times! In none of the above structures is carbon indicated to be bonded five times. Sorry for the trick question… In which of the following structures is carbon bonded five times? Functional Groups CHECK YOUR ANSWER

57. © 2012 Pearson Education, Inc. A.B.C.D. In which of the following structures is carbon bonded five times? Functional Groups CHECK YOUR NEIGHBOR

58. © 2012 Pearson Education, Inc. A.B.C.D. Explanation: Carbon can never be bonded five times! Structure C, therefore, is NOT a plausible structure for any existing organic compound. In which of the following structures is carbon bonded five times? Functional Groups CHECK YOUR ANSWER

59. © 2012 Pearson Education, Inc. Alcohols, Phenols, and Ethers

60. © 2012 Pearson Education, Inc. Alcohols Contain the Hydroxyl Group Hydroxyl Group

61. © 2012 Pearson Education, Inc. Methanol (bp 65°C)

62. © 2012 Pearson Education, Inc. Ethanol (bp 78°C)

63. © 2012 Pearson Education, Inc. 2-Propanol (bp 97°C)

64. © 2012 Pearson Education, Inc. Phenols Contain the Phenol Group Phenol

65. © 2012 Pearson Education, Inc. Phenols are acidic

66. © 2012 Pearson Education, Inc. Phenols are acidic

67. © 2012 Pearson Education, Inc. Phenols are acidic

68. © 2012 Pearson Education, Inc. Phenols are acidic H+H+

69. © 2012 Pearson Education, Inc. Phenols are acidic H+H+

70. © 2012 Pearson Education, Inc. Phenols are acidic H+H+

71. © 2012 Pearson Education, Inc. Phenols are acidic

72. © 2012 Pearson Education, Inc. Phenols are acidic

73. © 2012 Pearson Education, Inc. Phenols are acidic

74. © 2012 Pearson Education, Inc. Phenols are acidic

75. © 2012 Pearson Education, Inc. Phenols are acidic

76. © 2012 Pearson Education, Inc. Phenols are acidic

77. © 2012 Pearson Education, Inc. 4-n-Hexylresorcinol

78. © 2012 Pearson Education, Inc. Thymol

79. © 2012 Pearson Education, Inc. Ethers contain an oxygen bonded to two carbons Ether Group

80. © 2012 Pearson Education, Inc. Dimethyl ether (bp −25°C)

81. © 2012 Pearson Education, Inc. Dimethyl ether (bp −25°C) Ethanol bp 78°C

82. © 2012 Pearson Education, Inc. Diethyl ether

83. © 2012 Pearson Education, Inc. Amines and Alkaloids

84. © 2012 Pearson Education, Inc. Amines form alkaline solutions Amine Group

85. © 2012 Pearson Education, Inc. Ethyl amine

86. © 2012 Pearson Education, Inc.

91. Hydroxide ion

92. © 2012 Pearson Education, Inc. Caffeine Phosphoric acid

93. © 2012 Pearson Education, Inc. Phosphoric acid Caffeine salt

94. © 2012 Pearson Education, Inc. Phosphoric acid Caffeine salt Water soluble

95. © 2012 Pearson Education, Inc. Which of the following compounds should have a higher boiling point? A.Structure A. B.Structure B. C.Both the same. D.No way to tell. N H O Structure AStructure B Amines and Alkaloids CHECK YOUR NEIGHBOR

96. © 2012 Pearson Education, Inc. Which of the following compounds should have a higher boiling point? A.Structure A B.Structure B C.Both the same D.No way to tell Explanation: Structure B has a hydrogen attached to a strongly electronegative atom, nitrogen. This makes for a polar N—H bond that participates in hydrogen bonding. N H O Structure AStructure B Amines and Alkaloids CHECK YOUR ANSWER

97. © 2012 Pearson Education, Inc. Carbonyl Compounds

98. © 2012 Pearson Education, Inc. Carbonyl A carbon atom double bonded to an oxygen atom Carbonyl

99. © 2012 Pearson Education, Inc. Ketone Group

100. © 2012 Pearson Education, Inc. Ketone Group Aldehyde Group

101. © 2012 Pearson Education, Inc. Acetone

102. © 2012 Pearson Education, Inc. AcetoneAcetaldehyde

103. © 2012 Pearson Education, Inc. FormaldehydeAcetone

104. © 2012 Pearson Education, Inc. Citral

105. © 2012 Pearson Education, Inc. Cinnamonaldehyde

106. © 2012 Pearson Education, Inc. Benzaldehyde

107. © 2012 Pearson Education, Inc. Vanillin

108. © 2012 Pearson Education, Inc. Amide Group

109. © 2012 Pearson Education, Inc. N,N-Diethyl-m-toluamide DEET

110. © 2012 Pearson Education, Inc. Carboxyl group

111. © 2012 Pearson Education, Inc.

119. Salicylic acid

120. © 2012 Pearson Education, Inc. Acetylsalicylic acid Aspirin

121. © 2012 Pearson Education, Inc. Ester group

122. © 2012 Pearson Education, Inc. Salicylic acid

123. © 2012 Pearson Education, Inc. Salicylic acid H 2 SO 4 CH 3 OH

124. © 2012 Pearson Education, Inc. Methyl salicylate (Wintergreen)

125. © 2012 Pearson Education, Inc. Penicillin

126. © 2012 Pearson Education, Inc. The amino acid lysine is shown below. What functional group must be removed in order to produce the very smelly amine cadaverine, which is 1,5-pentanediamine? A.The hydrogen (shown) must be removed and replaced with an amino (NH 2 ) group. B.Lysine is 1,5-pentanediamine. Nothing has to be removed. C.The carboxyl group must be removed and replaced with a hydrogen. D.One amino group must be removed and replaced with a hydrogen. Lysine Carbonyl Compounds CHECK YOUR NEIGHBOR

127. © 2012 Pearson Education, Inc. The amino acid lysine is shown below. What functional group must be removed in order to produce the very smelly amine cadaverine, which is 1,5-pentanediamine? A.The hydrogen (shown) must be removed and replaced with an amino (NH 2 ) group. B.Lysine is 1,5-pentanediamine. Nothing has to be removed. C.The carboxyl group must be removed and replaced with a hydrogen. D.One amino group must be removed and replaced with a hydrogen. Lysine Carbonyl Compounds CHECK YOUR ANSWER

128. © 2012 Pearson Education, Inc. Polymers Polymer:A very long organic molecule made by the joining together of smaller organic molecule units known as monomers.

129. © 2012 Pearson Education, Inc. Polymers Polymer:A very long organic molecule made by the joining together of smaller organic molecule units known as monomers. Monomer

130. © 2012 Pearson Education, Inc. Polymers Addition Polymer: A polymer whose mass is equal to the sum of the masses of the monomer units.

131. © 2012 Pearson Education, Inc. Polymers Ethylene CC H H H H CC H H H H Addition Polymer: A polymer whose mass is equal to the sum of the masses of the monomer units.

132. © 2012 Pearson Education, Inc. Polymers Ethylene CC H H H H CC H H H H Addition Polymer: A polymer whose mass is equal to the sum of the masses of the monomer units.

133. © 2012 Pearson Education, Inc. Polymers Ethylene CC H H H H CC H H H H Addition Polymer: A polymer whose mass is equal to the sum of the masses of the monomer units.

134. © 2012 Pearson Education, Inc. Polymers Ethylene H CC H H H CC H H H H Addition Polymer: A polymer whose mass is equal to the sum of the masses of the monomer units.

135. © 2012 Pearson Education, Inc. Polymers Ethylene H CC H H H CC H HH H Addition Polymer: A polymer whose mass is equal to the sum of the masses of the monomer units.

136. © 2012 Pearson Education, Inc. Polymers H CC H H CC H HH HH Addition Polymer: A polymer whose mass is equal to the sum of the masses of the monomer units.

137. © 2012 Pearson Education, Inc. Polymers H CC H H CC H HH HH H CC H HH H CC H HH C H H H C H Addition Polymer: A polymer whose mass is equal to the sum of the masses of the monomer units.

138. © 2012 Pearson Education, Inc. Polymers H CC H H CC H HH HH H CC H HH H CC H HH C H H H C H Addition Polymer: A polymer whose mass is equal to the sum of the masses of the monomer units.

139. © 2012 Pearson Education, Inc. Polymers H CC H H CC H HH HH H CC H HH H CC H HH C H H H C H Ethylene Polyethylene C H H C H H

140. © 2012 Pearson Education, Inc. Polymers Propylene CC CH 3 H H H CC H H H Propylene

141. © 2012 Pearson Education, Inc. Polymers Polypropylene C H CC H H CC HH H H CC H HCH 3 CC HH H C HH H Propylene H C H C H CH 3

142. © 2012 Pearson Education, Inc. Polymers

143. © 2012 Pearson Education, Inc. Polymers

144. © 2012 Pearson Education, Inc. Polymers Condensation Polymer: A polymer formed when the joining of monomer units is accompanied by the loss of a small molecule, such as water.

145. © 2012 Pearson Education, Inc. Polymers

146. © 2012 Pearson Education, Inc. Polymers CONSIDER THIS… Many of the natural product molecules synthesized by plants are formed by the joining together of isoprene monomers via an addition polymerization. A good example is the flavoring molecule citral, which is made of two isoprene units. Find and circle these units within the structure shown to the right. Isoprene (2-methyl-1,3-butadiene) Citral Polymers

147. © 2012 Pearson Education, Inc. Many of the natural product molecules synthesized by plants are formed by the joining together of isoprene monomers via an addition polymerization. A good example is the flavoring molecule citral, which is made of two isoprene units. Find and circle these units within the structure shown to the right. Isoprene (2-methyl-1,3-butadiene) Citral Polymers

148. © 2012 Pearson Education, Inc. Beta-carotene is a natural addition polymer made of eight isoprene units. Find and circle these units within the structure shown below. Isoprene (2-methyl-1,3-butadiene) Beta-carotene Polymers

149. © 2012 Pearson Education, Inc. Beta-carotene is a natural addition polymer made of eight isoprene units. Find and circle these units within the structure shown below. Isoprene (2-methyl-1,3-butadiene) Beta-carotene Polymers