1. 1 Alcohols Ethers Amines Carbonyls Polymers Chapter 14 Organic Compounds

2. 2 Heteroatoms in Organic Compounds In organic molecules, C atoms form bonds  Mostly with H and other C atoms.  Sometimes Heteroatoms: atoms of O, N, S, and halogens F, Cl, and Br.

3. 3 Functional groups are  A characteristic feature of organic molecules that behave in a predictable way.  Composed of an atom or group of atoms.  Groups that replace a H in the corresponding alkane.  A way to classify families of organic compounds. Functional Groups

4. 4 Some Functional Groups

5. 5 Alcohols and Ethers  An alcohol contains the hydroxyl (-OH) functional group.  In an ether, an oxygen atom is bonded to two carbon atoms –C–O–C–. Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

6. 6 Alcohols and Phenols An alcohol contains  A hydroxyl group (—OH) attached to a carbon chain. A phenol contains  A hydroxyl group (—OH) attached to a benzene ring.

7. 7 Naming Alcohols The names of alcohols  In the IUPAC system replace -e of alkane name with -ol.  that are common names use the name of the alkyl group followed by alcohol. FormulaIUPACCommon Name CH 4 methane CH 3 ─OH methanol methyl alcohol CH 3 ─CH 3 ethane CH 3 ─CH 2 ─OH ethanol ethyl alcohol

8. 8 More Names of Alcohols In IUPAC names for longer carbon chains, the chain is numbered from the end nearest the ─OH group. CH 3 ─CH 2 ─CH 2 ─OH 1-propanol OH │ CH 3 ─CH─CH 2 ─CH 3 2-butanol CH 3 OH │ CH 3 ─CH─CH 2 ─CH 2 ─CH─CH 3 5-methyl-2-hexanol 6 5 4 3 2 1

9. 9 Some Typical Alcohols OH | “rubbing alcohol”CH 3 —CH—CH 3 2-propanol (isopropyl alcohol) antifreeze HO—CH 2 —CH 2 —OH 1,2-ethanediol (ethylene glycol) OH | glycerolHO—CH 2 —CH—CH 2 —OH 1,2,3-propanetriol (glycerol or glycerin)

10. 10 Learning Check Give the IUPAC name for each of the following: 1. CH 3 —CH 2 —CH 2 —CH 2 —OH OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 3.

11. 11 Solution 1. CH 3 —CH 2 —CH 2 —CH 2 —OH 1-butanol OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 3-methyl-2-pentanol 3. cyclopentanol

12. 12 Phenols in Medicine Phenol  Is the IUPAC name for benzene with a hydroxyl group.  Is used in antiseptics and disinfectants. phenol resorcinol 4-hexylresorcinol In throat lozenges

13. Phenols in Nature  Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint. Nutmeg Thyme Cloves Vanilla Wintergreen Methyl salicylate

14. 14 Write the structure of each of the following: A. 3-pentanol B. ethyl alcohol Learning Check

15. 15 Solution Write the structure of each of the following: A. 3-pentanol OH | CH 3 —CH 2 —CH—CH 2 —CH 3 B. ethyl alcohol CH 3 —CH 2 —OH

16. 16 Thiols  Often have strong odors.  Are used to detect gas leaks.  Are found in onions, oysters, and garlic. Are carbon compounds that contain a –SH group. Are named by adding ­thiol to the alkane name of the longest C chain.

17. 17 Ethers  Contain an ─O─ between two carbon groups.  That are simple are named by listing the alkyl names in alphabetical order followed by ether CH 3 ─O─CH 3 CH 3 ─CH 2 ─O─CH 3 dimethyl ether ethyl methyl ether

18. 18 Ethers as Anesthetics Anesthetics  Inhibit pain signals to the brain.  Such as ethyl ether CH 3 ─CH 2 ─O─CH 2 ─CH 3 were used for over a century, but caused nausea and were flammable.  Developed by 1960s were nonflammable. Cl F F Cl F H │ │ │ │ │ │ H─C─C─O─C─HH─C─C─O─C─H │ │ │ │ │ │ F F F H F H Ethane(enflurane) Penthrane

19. 19 MTBE Methyl tert-butyl ether CH 3 │ CH 3 ─O─C─CH 3 │ CH 3  Is one of the most produced organic chemicals.  Is a fuel additive  Is used to improve gasoline combustion.  Use is questioned since the discovery that MTBE has contaminated water supplies.

20. 20 Dioxins Dioxins are  A group of ethers that are highly toxic.  Formed during forest fires and as industrial by- products.  Often carcinogenic. 2,4,5-trichlorophenoxyacetic acid 2,3,7,8-tetrachlorodibenzodioxin (2,4,5-T; agent orange) (TTCC, “dioxin”)

21. 21 Boiling Points of Alcohols Alcohols  Contain a strongly electronegative O in the OH groups.  Form hydrogen bonds between alcohol molecules.  Have higher boiling points than alkanes and ethers of similar mass.

22. 22 Boiling Points of Ethers Ethers  Have an O atom, but no H is attached.  Cannot form hydrogen bonds between ether molecules.  Have boiling points similar to alkanes of similar mass.

23. 23 Solubility of Alcohols & Ethers in Water  Alcohols and ethers are more soluble in water than alkanes because the oxygen atom hydrogen bonds with water.  Alcohols with 1-4 C atoms are soluble, but alcohols with 5 or more C atoms are not.

24. 24 Comparing Solubility and Boiling Points CompoundMolarBoiling Soluble Mass Point (°C) in Water? Alkane CH 3 ─CH 2 ─CH 3 44-42 No Ether CH 3 ─O─CH 3 46-23 Yes Alcohol CH 3 ─CH 2 ─OH 46 78 Yes

25. 25 Solubility of Phenol Phenol  Is soluble in water.  Has a hydroxyl group that ionizes slightly (weak acid).  Is corrosive and irritating to the skin. + H 2 O + H 3 O +

26. Phenols are acidic since loss of H+ leaves a stable ion. The ion is stabilized by resonance which is distribution of the charge over the double bonds of the aromatic ring. Acidity of Phenol

27. 27 Learning Check Which compound would have the higher boiling point? Explain. ethyl methyl ether or 1-propanol

28. 28 Solution 1-propanol would have the higher boiling point because an alcohol can form hydrogen bonds, but the ether cannot. Which compound would have the higher boiling point? Explain. ethyl methyl ether or 1-propanol

29. 29 Learning Check Which compound would be more soluble in water? Explain. ethanol or 2-pentanol

30. 30 Solution Ethanol. An alcohol with two carbons in its carbon chain is more soluble than one with 5 carbons. The longer alkyl chain diminishes the effect of the –OH group. Which compound would be more soluble in water? Explain. ethanol or 2-pentanol

31. 31 Oxidation and Reduction In the oxidation of an organic compound  There is an increase in the number of C—O bonds.  There is a loss of H. In the reduction of an organic compound  There is an decrease in the number of C—O bonds.  There is a gain of H. Ethanol (Ethyl alcohol) Ethanal (Acetaldehyde) Ethanoic Acid (Acetic Acid)

32. 32 When a primary alcohol is oxidized [O],  One H is removed from the –OH.  Another H is removed from the carbon bonded to the OH.  An aldehyde is produced. [O] Primary alcohol Aldehyde OH O | [O] || CH 3 —C—H CH 3 —C—H + H 2 O | H Ethanol Ethanal (ethyl alcohol) (acetaldehyde) Oxidation of Primary (1  ) Alcohols

33. 33 Oxidation of Secondary (2  ) Alcohols When a secondary alcohol is oxidized [O],  One H is removed from the –OH.  Another H is removed from the carbon bonded to the OH.  A ketone is produced. [O] secondary alcohol ketone OH O │ [O] ║ CH 3 —C—CH 3 CH 3 —C—CH 3 + H 2 O │ H 2-propanone (dimethyl ketone, “acetone”) 2-propanol (isopropyl alcohol)

34. 34 Oxidation of Ethanol in the Body In the body,  Ethanol is oxidized by enzymes in the liver.  Aldehyde product impairs coordination. O ║ ║ CH 3 ─CH 2 ─OH CH 3 ─C─H CH 3 ─C─OH ethyl alcohol acetaldehyde acetic acid 2CO 2 + H 2 O

35. 35 Ethanol  Acts as a depressant.  Kills or disables more people than any other drug.  Is metabolized at a rate of 12-15 mg/dL per hour by a social drinker.  Is metabolized at a rate of 30 mg/dL per hour by an alcoholic. Ethanol CH 3 ─CH 2 ─OH

36. 36 Oxidation of Thiols When thiols undergo oxidation,  An H atom is lost from each of two –SH groups.  The product is a disulfide. [O] CH 3 —SH + HS—CH 3 CH 3 —S—S—CH 3 + H 2 O

37. 37 More Functional Groups

38. 38 Aldehydes and Ketones  An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom, attached to at least one hydrogen.  In a ketone, the carbon of the carbonyl group is attached to two other carbon atoms. Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

39. 39 Naming Aldehydes An aldehyde  Has an IUPAC name in which the -e in the alkane name is changed to -al.  Has a common name for the first four aldehydes that use the prefixes form­ (1C), acet­ (2C), propion­ (3C), and butyr­ (4C), followed by aldehyde. O O O ║ ║ ║ H − C − H CH 3 − C − HCH 3 − CH 2 − C − H methanal ethanal propanal (formaldehyde) (acetaldehyde) (propionaldehyde)

40. 40 Naming Aldehydes

41. 41 Aldehydes in Flavorings  Several naturally occurring aldehydes are used as flavorings for foods and fragrances. Benzaldehyde (almonds) Cinnamaldehyde (cinnamon) Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

42. 42 Naming Ketones Ketones are named  In the IUPAC system by replacing the -e in the alkane name with ­one. The carbonyl carbon is indicated by a number.  With a common name by indicating the alkyl groups attached to the carbonyl group in alphabetical order followed by ketone. O O ║ ║ CH 3 − C − CH 3 CH 3 − C − CH 2 − CH 3 propanone 2-butanone (dimethyl ketone) (ethyl methyl ketone)

43. 43 Ketones in Common Use Nail polish remover, Solvent Propanone, Dimethylketone, Acetone Butter flavoring

44. 44 Classify each as 1) aldehyde or 2) ketone. O O || || A. CH 3 —CH 2 —C—CH 3 B. CH 3 —C—H CH 3 O | || C. CH 3 —C—CH 2 —C—H D. | CH 3 Learning Check

45. 45 A. 2) ketone B. 1) aldehyde C. 1) aldehyde D. 2) ketone Solution

46. 46 Learning Check Classify each as an aldehyde (1), ketone (2), alcohol (3), or ether (4). O ║ A. CH 3 ─CH 2 ─C─CH 3 B. CH 3 ─O─CH 3 CH 3 O OH │ ║ │ C. CH 3 ─C─CH 2 ─C─HD. CH 3 ─CH─CH 3 │ CH 3

47. 47 Solution Classify each as an aldehyde (1), ketone (2), alcohol (3), or ether (4). O ║ A. CH 3 ─CH 2 ─C─CH 3 B. CH 3 ─O─CH 3 (2) ketone (4) ether CH 3 O OH │ ║ │ C. CH 3 ─C─CH 2 ─C─HD. CH 3 ─CH─CH 3 │ CH 3 (1) aldehyde (3) alcohol

48. 48 Polar Carbonyl Group & Boiling Point The polar carbonyl group  Provides dipole-dipole interactions.  +  -  +  - C=O C=O  Does not have H on the oxygen atom.  Cannot form hydrogen bonds. Aldehydes and ketones have  Higher boiling points than alkanes and ethers of similar mass.  Lower boiling points than alcohols of similar mass.

49. 49 Comparison of Boiling Points 58 Aldehydes and ketones have  Higher boiling points than alkanes and ethers of similar mass.  Lower boiling points than alcohols of similar mass.

50. 50 Learning Check Select the compound in each pair that would have the Higher boiling point. A. CH 3 —CH 2 —CH 3 or CH 3 —CH 2 —OH B. C. CH 3 —CH 2 —OH or CH 3 —O—CH 3

51. 51 Solution A. CH 3 —CH 2 —OH B. C. CH 3 —CH 2 —OH

52. 52 Solubility in Water The electronegative O atom of the carbonyl group in aldehydes and ketones forms hydrogen bonds with water.

53. 53 Learning Check Indicate if each is soluble or insoluble in water. A. CH 3 —CH 2 —CH 3 B. CH 3 —CH 2 —OH O || C. CH 3 —CH 2 —CH 2 —C—H O || D. CH 3 —C—CH 3

54. 54 Solution A. CH 3 —CH 2 —CH 3 insoluble B. CH 3 —CH 2 —OH soluble O || C. CH 3 —CH 2 —CH 2 —C—H soluble O || D. CH 3 —C—CH 3 soluble

55. 55 Carboxylic Acids and Esters  Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. O  — C—OH  An ester contains the carboxyl group between carbon atoms.

56. 56 Models of Carboxylic Acids  The three-dimensional models show the geometry of atoms in carboxylic acid molecules.

57. 57 The IUPAC names of carboxylic acids  Replace the -e in the alkane name with -oic acid. CH 4 methane HCOOH methanoic acid CH 3 —CH 3 ethane CH 3 —COOH ethanoic acid  Number substituents from the carboxyl carbon 1. CH 3 O | ║ CH 3 —CH—CH 2 —C—OH 4 3 2 1 3-methylbutanoic acid IUPAC Names

58. 58 The common names of simple carboxylic acids  Are formic acid (1C), acetic acid (2C), propionic acid (3C), and butyric acid (4C). HCOOH formic acid CH 3 —COOHacetic acid  Locate substituents using , , γ for the carbon atoms adjacent to the carboxyl carbon. CH 3 γ  |  CH 3 —CH—CH 2 —COOH 3-methylbutanoic acid (  -methylbutryic acid) Common Names

59. 59 Alpha Hydroxy Acids Alpha hydroxy acids (AHAs)  Occur naturally in fruit, milk, and sugarcane.  Are used in skin care products. Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

60. 60 Names and Sources of Some Carboxylic Acids TABLE 16.1 Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

61. 61 Common Carboxylic Acids Methanoic acid (formic acid) O ║ H─C─OH ethanoic acid (acetic acid) O ║ CH 3 ─C─OH Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

62. 62 Aromatic Carboxylic Acids Benzoic acid  Is the aromatic carboxylic acid.  Locates substituents by assigning 1 to the carbon attached to the carboxyl group.  Has common names that assign prefixes ortho, meta, and para for 2 substituents. ortho1, 2 location meta 1, 3 location para1, 4 location

63. 63 Aromatic Carboxylic Acids benzoic acid 3-chlorobenzoic acid 4-aminobenzoic acid m-chlorobenzoic acid p-aminobenzoic acid

64. 64 Preparation of Carboxylic Acids  Carboxylic acids can be prepared by oxidizing primary alcohols or aldehydes.  The oxidation of ethanol produces ethanoic acid (acetic acid). OH O O | [O] || [O] || CH 3 —CH 2 CH 3 —C—H CH 3 —C—OH ethanol ethanal ethanoic acid (ethyl alcohol) (acetaldehyde) (acetic acid)

65. 65 Boiling Points and Solubility TABLE 16.2 Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

66. 66 Acidity of Carboxylic Acids Carboxylic acids  Are weak acids.  Ionize in water to produce carboxylate ions and hydronium ions. O O ║ ║ CH 3 − C − OH + H 2 O CH 3 − C − O – + H 3 O + Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

67. 67 Neutralization of Carboxylic Acids Carboxylic acid salts  Are a product of the neutralization of a carboxylic acid with a strong base. CH 3 —COOH + NaOH CH 3 —COO – Na + + H 2 O acetic acid sodium acetate (carboxylic acid salt)  Are used as preservatives and flavor enhancers. Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

68. 68 Esters In an ester,  The H in the carboxyl group is replaced with an alkyl group. O  CH 3 — C—O—CH 3 ester group Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

69. 69 Ester Products Aspirin  Is used to relieve pain and reduce inflammation.  Is an ester of salicylic acid and acetic acid. Oil of wintergreen  Is used to soothe sore muscles.  Is an ester of salicylic acid and methanol.

70. 70 Esters in Plants Esters give flowers and fruits their pleasant fragrances and flavors. TABLE 16.4 Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

71. 71 In acid hydrolysis  An ester reacts with water to produce a carboxylic acid and an alcohol.  An acid catalyst is required. O  H + H—C—O—CH 2 —CH 3 + H 2 O O  H—C—OH + H—O—CH 2 —CH 3 Acid Hydrolysis of Esters

72. 72 Base hydrolysis (also called saponification)  Is the reaction of an ester with a strong base.  Produces the salt of the carboxylic acid and an alcohol. O || CH 3 —C—O—CH 2 —CH 3 + NaOH O  CH 3 —C—O – Na + + HO—CH 2 —CH 3 salt of carboxylic acid alcohol Base Hydrolysis (Saponification)

73. 73 “Soaps” The base hydrolysis of long chain fatty acids produces acid salts called “soaps”. Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

74. 74 Cleaning Action of Soap A soap  Contains a nonpolar end that dissolves in nonpolar fats and oils, and a polar end that dissolves in water.  Forms groups of soap molecules called micelles that dissolve in water and are washed away. Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

75. 75 Amines and Amides  In amines, the functional group is a nitrogen atom. | —N —  In amides, the hydroxyl group of a carboxylic acid is replaced by a nitrogen group.

76. 76 Amines CH 3 CH 3  CH 3 —NH 2 CH 3 —NH CH 3 —N—CH 3

77. 77 Simple amines  Are named as alkylamines.  List the names of the alkyl groups bonded to the N atom in alphabetical order in front of amine. CH 3 —CH 2 —NH 2 ethylamine CH 3 —NH—CH 3 dimethylamine CH 3 | CH 3 —N—CH 2 —CH 3 ethyldimethylamine Naming Amines: Common

78. 78 Boiling Points: of similar mass. Alcohols > Amines >Alkanes

79. 79 Hydrogen Bonding for Amines The polar N-H bond  Provides hydrogen bonding in 1°and 2° amines, but not 3°.  In amines is not as polar as the O-H bonds in alcohols.

80. 80 Solubility in Water Amines are soluble in water  If they have 1-5 carbon atoms.  Because the N atom in smaller amines forms hydrogen bonds with the polar O-H bond in water.

81. 81 Learning Check Consider the following compounds: 1. CH 3 —CH 2 —CH 2 —NH 2 2. CH 3 —CH 2 —NH—CH 3 3. CH 3 —CH 2 —CH 2 —CH 3 A. Which compound has the highest boiling point? B. Which compound(s) is(are) soluble in water?

82. 82 Solution Consider the following compounds: 1. CH 3 —CH 2 —CH 2 —NH 2 2. CH 3 —CH 2 —NH—CH 3 3. CH 3 —CH 2 —CH 2 —CH 3 A. Which compound has the highest boiling point? 1. CH 3 —CH 2 —CH 2 —NH 2 B. Which compound(s) is(are) soluble in water? 1. CH 3 —CH 2 —CH 2 —NH 2 2. CH 3 —CH 2 —NH—CH 3

83. 83 Amines are  Bronsted-Lowry bases that attract a H + from H 2 O to the N atom.  Weak bases in water. NH 3 + H 2 O NH 4 + + OH – ammonium hydroxide CH 3 —NH 2 + H 2 O CH 3 —NH 3 + + OH – methylammonium hydroxide Amines React as Bases

84. 84 An amine salt  Forms when an amine is neutralized by acid.  Is named by replacing the amine part of the name with ammonium followed by the name of the negative ion. CH 3 —NH 2 + HCl CH 3 —NH 3 + Cl – methylamine methylammonium chloride Neutralization forms Amine Salts

85. 85 Properties of Amine Salts Amine salts are  Solids at room temperature.  Soluble in water and body fluids.  The form used for drugs.

86. 86 Cocaine  Is sold illegally as an amine salt.  Is reacted with NaOH to produce the free amine form known as “crack”.

87. 87 Learning Check Write the equation for ethylamine when it reacts with each of the following: 1. + H 2 O 2. + HCl

88. 88 Solution Write the equation for ethylamine when it reacts with each of the following: 1. CH 3 —CH 2 —NH 2 + H 2 O CH 3 —CH 2 —NH 3 + OH – 2. CH 3 —CH 2 —NH 2 + HCl CH 3 —CH 2 —NH 3 + Cl –

89. 89 Alkaloids are  Physiologically active nitrogen-containing compounds.  Produced by plants.  Used as stimulants, anesthetics, and antidepressants.  Often habit forming. Alkaloids

90. 90 Caffeine  Is a stimulant of the central nervous system.  Is found in coffee beans, tea, chocolate, and soft drinks.  Contains an imidazole ring.

91. 91 Nicotine  Increases the adrenaline level in the blood.  Causes addiction to tobacco.  Contains a pyrrolidine ring.

92. 92 Alkaloids Related to Morphine Alkaloids  Such as morphine and codeine are produced by the poppy.  Have been used for centuries as painkillers.  Such as heroin and codeine are modifications of morphine.

93. 93 Pharmacology An area of research in pharmacology  Is to design drugs such as procaine, lidocaine, and demerol that retain some of the characteristics of alkaloids.  Is to modify the structures of cocaine and morphine to produce anesthesia, but without the addictive side effects.

94. 94 In amides, an amino group(–NH 2 ) replaces the –OH group of carboxylic acids. O || || CH 3 —C—OH CH 3 —C—NH 2 Amides

95. 95 Some Amides in Health and Medicine

96. 96 Summary of Functional Groups

97. 97 Functional Groups in Everyday Items Methyl amine (fish)

98. 98 Learning Check Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine. 1)CH 3 – CH 2 – CH 2 – OH 2) CH 3 – O – CH 2 – CH 3 3) CH 3 – CH 2 – NH 2 O O || || 4) CH 3 – C – OH 5) CH 3 – C – O – CH 3

99. 99 Solution Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine. 1)CH 3 ─CH 2 ─CH 2 ─OH 2) CH 3 ─O─CH 2 ─CH 3 alcohol ether 3) CH 3 ─CH 2 ─NH 2 amine O O || || 4) CH 3 ─C─OH 5) CH 3 ─C─O─CH 3 carboxylic acid ester

100. 100 Learning Check Identify the organic family for each: A. CH 3 ─CH 2 ─CH=CH 2 B. C. CH 3 ─C≡CH D.

101. 101 Solution Identify the organic family for each: A. CH 3 ─CH 2 ─CH=CH 2 alkene B. cycloalkane (alkane) C. CH 3 ─C≡CH alkyne D. aromatic

102. 102 Polymers Polymers are  Large, long-chain molecules.  Found in nature, including cellulose in plants, starches in food, proteins and DNA in the body.  Also synthetic such as polyethylene and polystyrene, Teflon, and nylon.  Made up of small repeating units called monomers.  Made by reaction of small alkenes.

103. 103 Common Synthetic Polymers

104. Polymers Polymer:A very long organic molecule made by the joining together of smaller organic molecule units known as monomers. Monomer

105. 105 Polymerization  In polymerization, small repeating units called monomers join to form a long chain polymer. monomer unit repeats n

106. 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.

107. 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.

108. 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.

109. 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.

110. 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.

111. 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.

112. 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.

113. Polymers H CC H H CC H HH HH H CC H HH H CC H HH C H H H C H H CC H H CC H HH HH H CC H HH H CC H HH C H H H C H Ethylene C H H C H H Polyethylene

114. 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 Propylene CC CH 3 H H H CC H H H Propylene

115. Polymers

117. 117 Learning Check Name the monomer used to make Teflon and write a portion of a Teflon polymer using four monomers.

118. 118 Solution F F │ │ F─C=C─F tetrafluoroethene F F F F F F F F │ │ │ │ │ │ │ │ ─C─C─C─C─C─C─C─C─ portion of Teflon │ │ │ │ │ │ │ │ F F F F F F F F

119. Condensation Polymers Formed when the joining of monomer units is accompanied by the loss of a small molecule, such as water.

120. 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

121. 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

122. 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

123. 123 Polymers from Addition Reactions

124. 124 More Monomers and Polymers

125. 125 Recycling Plastics Recycling is simplified by using codes found on plastic items. 1 PETE Polyethyleneterephtalate 2 HDPE High-density polyethylene 3 PV Polyvinyl chloride 4 LDPE Low-density polyethylene 5 PP Polypropylene 6 PS Polystyrene Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

126. 126 Learning Check What types of plastic are indicated by the following codes? A. B. C. 3 PV 5 PP 6 PS

127. 127 Solution What types of plastic are indicated by the following codes? A. Polyvinyl chloride B.Polypropylene C.Polystyrene. 3 PV 5 PP 6 PS

128. (Alcohol) Learning Check

129. (Alcohol) Solution

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131. (Alcohol) Learning Check

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134. (Alcohol) Learning Check

135. Lemon Fragrance (Alcohol) Solution

136. (Alcohol) Learning Check

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139. (Alcohol) Learning Check

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141. (Alcohol) Learning Check

142. Raspberry flavor (Alcohol) Solution

143. (Alcohol) Learning Check

144. Wintergreen flavor (Alcohol) Solution

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146. (Alcohol) Learning Check

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149. (Alcohol) Phenyl group Solution

150. (Alcohol) Learning Check

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154. (Alcohol) Solution