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Substituted Hydrocarbons and Their Reactions
Section 22.1 Alkyl Halides and Aryl Halides
Section Alcohols, Ethers, and Amines
Section Carbonyl Compounds
Section Other Reactions of Organic Compounds
Section 22.5 Polymers
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3. Section 22.1 Alkyl Halides and Aryl Halides
Define functional group, and give examples.
aliphatic compound: a nonaromatic hydrocarbon, such as an alkane, an alkene, or an alkyne
Compare and contrast alkyl and aryl halide structures.
Evaluate the boiling points of organic halides.
Section 22-1

4. Section 22.1 Alkyl Halides and Aryl Halides (cont.)
functional group
halocarbon
alkyl halide
aryl halide
plastic
substitution reaction
halogenation
A halogen atom can replace a hydrogen atom in some hydrocarbons.
Section 22-1

5. Functional Groups
In an organic molecule, a functional group is an atom or group of atoms that always reacts in a certain way.
Addition of a functional group to a hydrocarbon always produces a substance with different chemical and physical properties.
Double and triple bonds between carbon atoms are considered functional groups.
Section 22-1

6. Functional Groups (cont.)
Section 22-1

7. Organic Compounds Containing Halogens
Any organic compound that contains a halogen substituent is called a halocarbon.
An alkyl halide is an organic compound containing a halogen atom covalently bonded to an aliphatic carbon atom.
An aryl halide is an organic compound containing a halogen bonded to an aromatic group.
Section 22-1

8. Organic Compounds Containing Halogens (cont.)
In naming halocarbons, a prefix indicates which halogen is present.
If there is more than a single halogen, they are listed alphabetically.
Section 22-1

9. Organic Compounds Containing Halogens (cont.)
Halocarbons have higher boiling points because they have an increasing tendency to form temporary dipoles.
Dipoles attract each other, and require more energy to separate.
A plastic is a polymer that can be heated and molded while relatively soft.
Section 22-1

10. Organic Compounds Containing Halogens (cont.)
Section 22-1

11. Substitution Reactions
Nearly all synthetic organic compounds begin with petroleum.
A substitution reaction is one in which one atom or a group of atoms in a molecule is replaced by another atom or group of atoms
Hydrogen atoms in an alkane can be replaced by atoms of halogens in a process called halogenation.
Section 22-1

12. Substitution Reactions (cont.)
Section 22-1

13. Substitution Reactions (cont.)
Once halogenated, alkanes can undergo further reactions.
Reacting an alkyl halide with a basic solution results in replacement of the halogen atom with an –OH group to form an alcohol.
Section 22-1

14. A B C D Section 22.1 Assessment
Which of the following is NOT an alkyl halide?
A. 2-fluorobutane
B. 1,3-dichlorobenzene
C. sodium chloride
D. bromoethane A B C D
Section 22-1

15. A B C D Section 22.1 Assessment
An alkane with one or more halogen substituents is called what?
A. aryl halide
B. metal halide
C. chlorofluorocarbon
D. alkyl halide A B C D
Section 22-1

16. End of Section 22-1

17. Section 22.2 Alcohols, Ethers, and Amines
Identify the functional groups that characterize alcohols, ethers, and amines.
miscible: describes two liquids that are soluble in each other
Draw the structures of alcohols, ethers, and amines.
Discuss the properties and uses of alcohols, ethers, and amines.
Section 22-2

18. Section 22.2 Alcohols, Ethers, and Amines (cont.)
hydroxyl group
alcohol
denatured alcohol
ether
amine
Oxygen and nitrogen are two of the most-common atoms found in organic functional groups.
Section 22-2

19. Oxygen commonly forms two covalent bonds to form a stable octet.
Alcohols
Oxygen commonly forms two covalent bonds to form a stable octet.
An oxygen-hydrogen group covalently bonded to a carbon atom is called a hydroxyl group.
An organic compound in which a hydroxyl group replaces a hydrogen is called an alcohol.
Section 22-2

20. Alcohols (cont.)
Section 22-2

21. Alcohol is polar and mixes completely with water.
Alcohols (cont.)
Alcohol is polar and mixes completely with water.
Denatured alcohol is ethanol with small amounts of noxious materials added to it.
Alcohol names are based on the alkane names, with the ending –ol.
Section 22-2

22. Ethers
An ether is an organic compound containing an oxygen bonded to two carbon atoms.
Section 22-2

23. Ethers are volatile and have low boiling points.
Ethers (cont.)
Ethers have no hydrogen atoms bonded to their oxygen atoms, so they cannot form hydrogen bonds with each other.
Ethers are volatile and have low boiling points.
Ethers with identical chains are named by the chain followed by the word ether.
Ethers with different chains are named in alphabetical order followed by ether.
Section 22-2

24. Amines
Amines contain nitrogen atoms bonded to carbon atoms in aliphatic chains or aromatic rings.
Section 22-2

25. Amines have the suffix –amine.
Amines (cont.)
Amines are primary, secondary, or tertiary depending on if there are one, two, or three hydrogen atoms replaced by organic groups.
Amines have the suffix –amine.
Section 22-2

26. A B C D Section 22.2 Assessment Which of the following is an alcohol?
A. cyclohexamine
B. 1-chlorobutanol
C. bromobutene
D. butylpropyl ether A B C D
Section 22-2

27. A B C D Section 22.2 Assessment
Which functional group is present in an alcohol?
A. hydroxyl group
B. halogen
C. aromatic ring
D. amino group A B C D
Section 22-2

28. End of Section 22-2

29. Section 22.3 Carbonyl Compounds
Identify the structures of carbonyl compounds, including aldehydes, ketones, carboxylic acids, esters, and amides.
electronegative: indicates the relative ability of an element’s atoms to attract electrons in a chemical bond
Discuss the properties of compounds containing the carbonyl group.
Section 22-3

30. Section 22.3 Carbonyl Compounds (cont.)
carbonyl group
aldehyde
ketone
carboxylic acid
carboxyl group
ester
amide
condensation reaction
Carbonyl compounds contain a double-bonded oxygen in the functional group.
Section 22-3

31. Organic Compounds Containing the Carbonyl Group
An oxygen atom double-bonded to a carbon atom is a carbonyl group.
Aldehydes are organic compounds in which the carbonyl group is located at the end of the carbon chain and is bonded to a carbon atom on one side and a hydrogen on the other side.
Aldehydes are named with the suffix –al.
Section 22-3

32. Organic Compounds Containing the Carbonyl Group (cont.)
Section 22-3

33. Organic Compounds Containing the Carbonyl Group (cont.)
A ketone is an organic compound in which the carbon of the carbonyl group is bonded to two other carbon atoms.
Ketones are named by changing the –e at the end of the alkane name to –one, and including a number before the name to indicate the position of the ketone group.
Ketones and aldehydes share many chemical and physical properties because their structures are similar.
Section 22-3

34. Organic Compounds Containing the Carbonyl Group (cont.)
Ketones are popular solvents for moderately polar substances.
Ketones are somewhat soluble in water.
Section 22-3

35. Organic Compounds Containing the Carbonyl Group (cont.)
Section 22-3

36. Carboxylic acids are organic compounds that have a carboxyl group.
Carboxyl groups are carbonyls bonded to a hydroxyl group
Carboxylic acids are named by changing the –ane to –anoic acid.
Section 22-3

37. Carboxylic Acids (cont.)
Section 22-3

38. Carboxylic Acids (cont.)
Carboxylic groups are represented by –COOH.
Carboxylic acids are polar and reactive, and ionize in water to form acids.
Section 22-3

39. Organic Compounds Derived from Carboxylic Acids
An ester is any organic compound with a carboxyl group in which the hydrogen in the hydroxyl group is replaced by an alkyl chain.
Section 22-3

40. Organic Compounds Derived from Carboxylic Acids (cont.)
To name an ester, write the alkyl group followed by the name of the acid with the –oic acid ending replaced with –oate.
Esters are polar molecules and many are volatile and sweet smelling.
Many esters are found in fruits and flowers.
Section 22-3

41. Organic Compounds Derived from Carboxylic Acids (cont.)
An amide group is an organic compound in which the –OH group of a carboxylic acid is replaced by a nitrogen atom bonded to other atoms.
Section 22-3

42. Organic Compounds Derived from Carboxylic Acids (cont.)
The amide functional group is found repeated many times in natural proteins and some synthetic materials.
Section 22-3

43. Condensation Reactions
In a condensation reaction, two smaller organic molecules combine to form a more complex molecule, accompanied by the loss of a small molecule such as water.
Condensation reactions are elimination reactions that form bonds between two atoms not previously bonded.
Section 22-3

44. A B C D Section 22.3 Assessment
Which of the following is the carbonyl group?
A. COOH
B. C=O
C. CONH2
D. R-O-R′ A B C D
Section 22-3

45. A B C D Section 22.3 Assessment
Which of the following does NOT contain a carbonyl group?
A. ketones
B. esters
C. amines
D. aldehydes A B C D
Section 22-3

46. End of Section 22-3

47. Section 22.4 Other Reactions of Organic Compounds
Classify an organic reaction into one of five categories: substitution, addition, elimination, oxidation-reduction, or condensation.
Use structural formulas to write equations for reactions of organic compounds.
Predict the products of common types of organic reactions.
catalyst: a substance that increases the rate of a chemical reaction by lowering activation energies but is not consumed in the reaction
Section 22-4

48. Section 22.4 Other Reactions of Organic Compounds (cont.)
elimination reaction
dehydrogenation reaction
dehydration reaction
addition reaction
hydration reaction
hydrogenation reaction
Classifying the chemical reactions of organic compounds makes predicting products of reactions much easier.
Section 22-4

49. Classifying Reactions of Organic Substances
Using combinations of reactions allows chemical industries to convert simple molecules from petroleum and natural gas into large, complex organic molecules.
Section 22-4

50. Classifying Reactions of Organic Substances (cont.)
The formation of alkenes from alkanes is an elimination reaction, a reaction in which a combination of atoms is removed from two adjacent atoms forming an additional bond between the two carbon atoms.
Section 22-4

51. Classifying Reactions of Organic Substances (cont.)
A reaction that eliminates two hydrogen atoms is called a dehydrogenation reaction.
Section 22-4

52. Classifying Reactions of Organic Substances (cont.)
An elimination reaction in which the atoms removed form water is called a dehydration reaction.
Section 22-4

53. Classifying Reactions of Organic Substances (cont.)
Addition reactions result when other atoms bond to two atoms bonded by a double or triple covalent bonds.
A hydration reaction is an addition reaction in which a hydrogen atom and hydroxyl group from a water molecule add to a double or triple bond.
Section 22-4

54. Classifying Reactions of Organic Substances (cont.)
A hydrogenation reaction involves the addition of hydrogen to atoms in a double or triple bond.
Catalysts are usually needed in hydrogenation reactions.
Hydrogenation reactions are commonly used to convert liquid unsaturated fats into saturated fats that are solid at room temperature.
Section 22-4

55. Classifying Reactions of Organic Substances (cont.)
Section 22-4

56. Classifying Reactions of Organic Substances (cont.)
Many organic compounds can be converted to other compounds by oxidation-reduction reactions.
Section 22-4

57. Classifying Reactions of Organic Substances (cont.)
Section 22-4

58. Predicting Products of Organic Reactions
Each type of reaction—substitution, addition, elimination, oxidation-reduction, and condensation—can be used to predict the products of other organic reactions of the same types.
Section 22-4

59. A B C D Section 22.4 Assessment
Which type of reaction normally produces an alcohol from an alkene?
A. substitution
B. elimination
C. hydration
D. addition A B C D
Section 22-4

60. A B C D Section 22.4 Assessment
What type of reaction is the following?
alkyl halide → alkene
A. halogenation
B. elimination
C. addition
D. substitution A B C D
Section 22-4

61. End of Section 22-4

62. Section Polymers
Diagram the relationship between a polymer and the monomers from which it forms.
molecular mass: the mass of one molecule of a substance
Classify polymerization reactions as addition or condensation.
Predict polymer properties based on their molecular structures and the presence of functional groups.
Section 22-5

63. Section 22.5 Polymers (cont.)
monomer
polymerization reaction
addition polymerization
condensation polymerization
thermoplastic
thermosetting
Synthetic polymers are large organic molecules made up of repeating units that are linked together by addition or condensation reactions.
Section 22-5

64. The Age of Polymers
Polymers are large molecules consisting of many repeating structural units.
The turn of the 20th century saw the advent of such polymers as rubber and celluloid.
Section 22-5

65. Reactions Used to Make Polymers (cont.)
A monomer is a molecule from which a polymer is made.
A reaction in which monomer units are bonded together to form a polymer are called polymerization reactions.
In addition polymerization all of the atoms present in the monomers are retained in the polymer product.
Section 22-5

66. Reactions Used to Make Polymers (cont.)
Section 22-5

67. Reactions Used to Make Polymers (cont.)
Section 22-5

68. Reactions Used to Make Polymers (cont.)
Section 22-5

69. Reactions Used to Make Polymers (cont.)
Condensation polymerization takes place when monomers containing at least two functional groups combine with the loss of a small by-product, usually water.
Section 22-5

70. Properties and Recycling of Polymers
Polymers are inexpensive and easy to make.
Polymers have a wide range of properties.
They are easy to mold into different shapes.
Thermoplastic polymers can be melted and molded repeatedly into shapes that are retained when cooled.
Thermosetting polymers can be molded when first prepared, but cannot be remelted.
Section 22-5

71. Properties and Recycling of Polymers (cont.)
As fossil fuel supplies are depleted, recycling polymers becomes more important.
Section 22-5

72. A B C D Section 22.5 Assessment
The smaller, repeating units that make up a polymer are called ____.
A. structural units
B. polyunits
C. monomers
D. building blocks A B C D
Section 22-5

73. A B C D Section 22.5 Assessment
One way polymers are synthesized is through ____ reactions.
A. condensation
B. elimination
C. substitution
D. dehydration A B C D
Section 22-5

74. End of Section 22-5

75. Standardized Test Practice Image Bank Concepts in Motion
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Chapter Assessment
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76. Section 22.1 Alkyl Halides and Aryl Halides
Key Concepts
The substitution of functional groups for hydrogen in hydrocarbons creates a wide variety of organic compounds.
An alkyl halide is an organic compound that has one or more halogen atoms bonded to a carbon atom in an aliphatic compound.
Study Guide 1

77. Section 22.2 Alcohols, Ethers, and Amines
Key Concepts
Alcohols, ethers, and amines are formed when specific functional groups substitute for hydrogen in hydrocarbons.
Because they readily form hydrogen bonds, alcohols have higher boiling points and higher water solubilities than other organic compounds.
Study Guide 2

78. Section 22.3 Carbonyl Compounds
Key Concepts
Carbonyl compounds are organic compounds that contain the C=O group.
Five important classes of organic compounds containing carbonyl compounds are aldehydes, ketones, carboxylic acids, esters, and amides.
Study Guide 3

79. Section 22.4 Other Reactions of Organic Compounds
Key Concepts
Most reactions of organic compounds can be classified into one of five categories: substitution, elimination, addition, oxidation-reduction, and condensation.
Knowing the types of organic compounds reacting can enable you to predict the reaction products.
Study Guide 4

80. Polymers are synthesized through addition or condensation reactions.
Section Polymers
Key Concepts
Polymers are large molecules formed by combining smaller molecules called monomers.
Polymers are synthesized through addition or condensation reactions.
The functional groups present in polymers can be used to predict polymer properties.
Study Guide 5

81. A B C D Aryl halides contain what two groups?
A. nitrogen and aliphatic hydrocarbon chain
B. nitrogen and aromatic hydrocarbon ring
C. halogen and aromatic hydrocarbon ring
D. halogen and aliphatic hydrocarbon chain A B C D
Chapter Assessment 1

82. A B C D Amines contain which function group? A. –OH B. –Br C. R-O-R′
D. –NH2 A B C D
Chapter Assessment 2

83. A B C D Which of the following does NOT contain the carbonyl group?
A. ketones
B. ethers
C. aldehydes
D. amides A B C D
Chapter Assessment 3

84. What is an addition reaction in which a hydrogen atom and hydroxyl group from a water molecule add to a double or triple bond called?
A. elimination reaction
B. hydration reaction
C. dehydration reaction
D. hydrogenation reaction A B C D
Chapter Assessment 4

85. A type of plastic that can be molded only when first produced is called a ____.
A. thermoplastic
B. polythermal
C. setting plastic
D. thermosetting A B C D
Chapter Assessment 5

86. A B C D What are the products of this reaction? CH3CH2Br + NaOH → ____
A. CH3CH2Na + BrOH
B. CH3CH2OH + NaBr
C. CH3CH2OHNaBr
D. CH3CH3 + Na3BrO A B C D
STP 1

87. A B C D What type of compound does this formula represent?
CH3CH2CH2COOH
A. ester
B. ether
C. carboxylic acid
D. ketone A B C D
STP 2

88. A B C D How many carbon atoms are present in 2-ethyl pentane? A. 2
STP 3

89. A B C D What are the oxidation numbers of the elements in H2SO4?
A. H = +1, S = +6, O = –2
B. H = +2, S = +4, O = –4
C. H = +1, S = +4, O = –1
D. H = +1, S = –10, O = +2 A B C D
STP 4

90. A B C D Which type of compound is formed when accepts H+ ions?
A. Brønsted-Lowery base
B. Brønsted-Lowery acid
C. conjugate base
D. conjugate acid A B C D
STP 5

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92. IB 1

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95. IB 4

96. IB 5

97. IB 6

98. IB 7

99. IB 8

100. IB 9

101. IB 10

102. IB 11

103. IB 12

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114. IB 23

115. Table 22.1 Organic Compounds and Their Functional Groups
Table Common Polymers
CIM

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