1. Chapter 22 Organic Chemistry
John E. McMurray and Robert C. Fay
General Chemistry: Atoms First
Chapter 22 Organic Chemistry
Prentice Hall

2. Uses of Hydrocarbons Number of C atoms State Major Uses 1-4 gas
heating and cooking fuel
5-7
liquids,
(low boiling)
solvents, gasoline
6-18
liquids
gasoline
12-24
jet fuel; camp stove fuel
18-50
(high boiling)
diesel fuel, lubricants, heating oil
50+
solids
petroleum jelly, paraffin wax
1-4
gas
heating and cooking fuel
5-7
liquids,
(low boiling)
solvents, gasoline
6-18
liquids
gasoline
12-24
liquids
jet fuel; camp stove fuel
18-50
liquids,
(high boiling)
diesel fuel, lubricants, heating oil
50+
solids
petroleum jelly, paraffin wax

3. Structure Determines Properties
Organic compounds all contain carbon
CO, CO2 , carbonates and carbides are inorganic
other common elements are H, O, N, (P, S)
Carbon has versatile bonding patterns
chains, rings, single, double and triple bonds
chain length nearly limitless
Carbon compounds generally covalent
C - C bonds unreactive (very stable)

4. Bond Energies and Reactivities

5. alkynes
alkanes
alkenes

6. Methane - 1 Carbon
Ethane - 2 Carbon Chain
Propane - 3 Carbon Chain
Butane - 4 Carbon Chain
Pentane - 5 Carbon Chain
Hexane - 6 Carbon Chain
Heptane - 7 Carbon Chain
Octane - 8 Carbon Chain
Nonane - 9 Carbon Chain
Decane Carbon Chain

7. The Nature of Organic Molecules
Chapter 22: Organic Chemistry
4/17/2017
The Nature of Organic Molecules
Organic Chemistry: The study of carbon compounds.
Carbon is tetravalent. It has four outer-shell electrons (1s22s22p2) and forms four bonds.
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8. The Nature of Organic Molecules
Chapter 22: Organic Chemistry
4/17/2017
The Nature of Organic Molecules
Organic molecules have covalent bonds. In ethane, for instance, all bonds result from the sharing of two electrons.
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9. The Nature of Organic Molecules
Chapter 22: Organic Chemistry
4/17/2017
The Nature of Organic Molecules
Organic molecules have polar covalent bonds when carbon bonds to an element on the right or left side of the periodic table.
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10. The Nature of Organic Molecules
Chapter 22: Organic Chemistry
4/17/2017
The Nature of Organic Molecules
Carbon can form multiple covalent bonds by sharing more than two electrons with a neighboring atom.
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11. The Nature of Organic Molecules
Chapter 22: Organic Chemistry
4/17/2017
The Nature of Organic Molecules
Organic molecules have specific three-dimensional shapes, which can be predicted by the VSEPR model.
Copyright © 2010 Pearson Prentice Hall, Inc.

12. The Nature of Organic Molecules
Chapter 22: Organic Chemistry
4/17/2017
The Nature of Organic Molecules
Organic molecules have specific three-dimensional shapes, which can be predicted by the VSEPR model.
Copyright © 2010 Pearson Prentice Hall, Inc.

13. The Nature of Organic Molecules
Chapter 22: Organic Chemistry
4/17/2017
The Nature of Organic Molecules
Carbon uses hybrid atomic orbitals for bonding.
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14. Alkanes and Their Isomers
Chapter 22: Organic Chemistry
4/17/2017
Alkanes and Their Isomers
Hydrocarbons: Molecules that contain only carbon and hydrogen.
Alkanes: Hydrocarbons that contain only single bonds.
Space-filling models:
Structural formulas:
Molecular formulas:
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15. Chapter 22: Organic Chemistry
4/17/2017
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16. Alkanes and Their Isomers
Chapter 22: Organic Chemistry
4/17/2017
Alkanes and Their Isomers
Isomers: Compounds with the same molecular formula but different chemical structures.
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17. Isomerism
Isomers = different molecules with the same molecular formula
Structural Isomers = different pattern of atom attachment
Constitutional Isomers
Stereoisomers = same atom attachments, different spatial orientation

18. Free Rotation Around C─C

19. Rotation about a bond is not isomerism

20. Structural Isomers of C4H10
Butane, BP = 0°C
Isobutane, BP = -12°C

21. Possible Structural Isomers

22. Geometric Isomerism
because the rotation around a double bond is highly restricted, you will have different molecules if groups have different spatial orientation about the double bond
this is often called cis-trans isomerism
when groups on the doubly bonded carbons are cis, they are on the same side
when groups on the doubly bonded carbons are trans, they are on opposite sides

23. Cis-Trans Isomerism

24. Drawing Structural Formulas
4-ethyl-2-methylhexane
draw and number the base chain carbon skeleton
add the carbon skeletons of each substituent on the appropriate main chain C
add in required H’s

25. Practice – Draw the structural formula of 4-isopropyl-2-methylheptane

26. Practice – Draw the structural formula of 4-isopropyl-2-methylheptane

27. Drawing Organic Structures
Chapter 22: Organic Chemistry
4/17/2017
Drawing Organic Structures
Structural
Formula
Condensed Formula
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28. Ex 20.1 – Write the structural formula of all isomers and carbon skeleton formula for C6H14
start by connecting the carbons in a line
determine the C skeleton of the other isomers

29. Ex 20.1 – Write the structural formula and carbon skeleton formula for C6H14
fill in the H to give each C 4 bonds

30. Ex 20.1 – Write the structural formula and carbon skeleton formula for C6H14
convert each to a carbon skeleton formula – each bend and the ends represent C atoms

31. Stereoisomers
stereoisomers are different molecules whose atoms are connected in the same order, but have a different spatial direction, they can be:
optical isomers - molecules that are non-superimposable mirror images of each other
geometric isomers - stereoisomers that are not optical isomers

32. Optical Isomers - Nonsuperimposable Mirror Images
mirror image cannot be rotated so all its atoms align
with the same atoms of the original molecule

33. Chirality
any molecule with a non-superimposable mirror image is said to be chiral
any carbon with 4 different substituents is called a chiral center
a pair of non-superimposable mirror images are called a pair of enantiomers

34. Optical Isomers of 3-methylhexane

35. Plane Polarized Light
light that has been filtered so that only those waves traveling in a single plane are allowed through

36. Optical Activity
a pair of enantiomers have all the same physical properties except one – the direction they rotate the plane of plane polarized light
each will rotate the plane the same amount, but in opposite directions
dextrorotatory = rotate to the right
levorotatory = rotate to the left
an equimolar mixture of the pair is called a racemic mixture
rotations cancel, so there is no net rotation of light

37. Chemical Behavior of Enantiomers
a pair of enantiomers will have the same chemical reactivity in a non-chiral environment
but in a chiral environment they may exhibit different behaviors
enzyme selection of one enantiomer of a pair

38. The Shapes of Organic Molecules
Chapter 22: Organic Chemistry
4/17/2017
The Shapes of Organic Molecules
Condensed formulas do not indicate the shape.
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39. Chapter 22: Organic Chemistry
4/17/2017
Naming Alkanes
IUPAC Rules
-ane suffix since they are alkanes
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40. Chapter 22: Organic Chemistry
4/17/2017
Naming Alkanes
Name the main chain. Find the longest continuous chain of carbons in the molecule, and use the name of that chain as the parent name:
Copyright © 2010 Pearson Prentice Hall, Inc.

41. Chapter 22: Organic Chemistry
4/17/2017
Naming Alkanes
Number the carbon atoms in the main chain. Beginning at the end nearer the first branch point, number each carbon atom in the parent chain:
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42. Chapter 22: Organic Chemistry
4/17/2017
Naming Alkanes
Identify and number the branching substituent. Assign a number to each branching substituent group on the parent chain according to its point of attachment:
Copyright © 2010 Pearson Prentice Hall, Inc.

43. Chapter 22: Organic Chemistry
4/17/2017
Naming Alkanes
Identify and number the branching substituent. Assign a number to each branching substituent group on the parent chain according to its point of attachment:
Copyright © 2010 Pearson Prentice Hall, Inc.

44. Chapter 22: Organic Chemistry
4/17/2017
Naming Alkanes
Write the name as a single word. Use hyphens to separate the different prefixes, and use commas to separate numbers when there are more than one. If two or more different substituent groups are present, list them in alphabetical order. If two or more identical substituent groups are present, use one of the Greek prefixes:
The Greek prefixes are not used when alphabetizing substituent groups.
This is continued on the next slide.
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45. Chapter 22: Organic Chemistry
4/17/2017
Naming Alkanes
Copyright © 2010 Pearson Prentice Hall, Inc.

46. Chapter 22: Organic Chemistry
4/17/2017
Naming Alkanes
Copyright © 2010 Pearson Prentice Hall, Inc.

47. Chapter 22: Organic Chemistry
4/17/2017
Naming Alkanes
Copyright © 2010 Pearson Prentice Hall, Inc.

48. Example – Name the alkane
find the longest continuous C chain and use it to determine the base name
since the longest chain has 5 C
the base name is pentane

49. Example – Name the alkane
identify the substituent branches
there are 2 substituents
both are 1 C chains, called methyl

50. Example – Name the alkane
number the chain from the end closest to a substituent branch
if first substituents equidistant from end, go to next substituent in
then assign numbers to each substituent based
on the number of the main chain C it’s attached to
both substituents are equidistant from the end

51. Example – Name the alkane
write the name in the following order
substituent number of first alphabetical substituent followed by dash
substituent name of first alphabetical substituent followed by dash
if it’s the last substituent listed, no dash
use prefixes to indicate multiple identical substituents
repeat for other substituents alphabetically
name of main chain
2,4 –
dimethyl
pentane

52. Practice – Name the Following

53. Practice – Name the Following
3-ethyl-2-methylpentane

54. Chapter 22: Organic Chemistry
4/17/2017
Cycloalkanes
Cycloalkane: One or more rings of carbon atoms.
These are sometimes called line-angle formulas and can be done with any hydrocarbon.
3 C
4 C
5 C
6 C
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55. Chapter 22: Organic Chemistry
4/17/2017
Cycloalkanes
Carbon #1 is assumed to be attached to the substituent group in simple cyclic compounds.
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56. Chapter 22: Organic Chemistry
4/17/2017
Cycloalkanes
With multiple alkyl substituents, number the carbons in the cycloalkane alphabetically.
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57. Chapter 22: Organic Chemistry
4/17/2017
Reactions of Alkanes
Combustion:
CO2(g) + 2H2O(l)
CH4(g) + 2O2(g)
∆H° = -802 kJ
Halogens (Cl2 or Br2):
This combustion reaction assumes complete combustion and no production of carbon monoxide.
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58. Reactions of Hydrocarbons
all hydrocarbons undergo combustion
combustion is always exothermic
about 90% of U.S. energy generated by combustion
2 CH3CH2CH2CH3(g) + 13 O2(g) → 8 CO2(g) + 10 H2O(g)
CH3CH=CHCH3(g) + 6 O2(g) → 4 CO2(g) + 4 H2O(g)
2 CH3CCCH3(g) + 11 O2(g) → 8 CO2(g) + 6 H2O(g)

59. Other Alkane Reactions
Substitution
replace H with a halogen atom
initiated by addition of energy in the form of heat or ultraviolet light
to start breaking bonds
generally get multiple products with multiple substitutions

60. Families of Organic Molecules: Functional Groups
Chapter 22: Organic Chemistry
4/17/2017
Families of Organic Molecules: Functional Groups
Functional Group: An atom or group of atoms within a molecule that has a characteristic chemical behavior and that undergoes the same kinds of reactions in every molecule where it occurs.
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61. Chapter 22: Organic Chemistry
4/17/2017
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62. Chapter 22: Organic Chemistry
4/17/2017
This table is very large and would probably work better as a handout in class.
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63. Chapter 22: Organic Chemistry
4/17/2017
Alkenes and Alkynes
Alkene: A hydrocarbon that contains a carbon-carbon double bond.
Alkyne: A hydrocarbon that contains a carbon-carbon triple bond.
Unsaturated: A hydrocarbon that contains fewer hydrogens per carbon than the related alkane.
Saturated: A hydrocarbon that contains the maximum possible number of hydrogens.
Copyright © 2010 Pearson Prentice Hall, Inc.

64. Examples of Naming Alkenes
H H H
H C C C C C H
H CH3 H H H
2-methyl-1-pentene
H CH H H
H C C C C C C H
H CH3 CH H H H
CH3 CH3
3-isopropyl-2,2-dimethyl-3-hexene

65. since the longest chain with the double bond has 6 C
Name the Alkene
find the longest, continuous C chain that contains the double bond and use it to determine the base name
since the longest chain with the double bond has 6 C
the base name is hexene

66. Name the Alkene identify the substituent branches
there are 2 substituents
one is a 1 C chain, called methyl
the other one is a 2 C chain, called ethyl

67. Name the Alkene
number the chain from the end closest to the double bond
then assign numbers to each substituent based
on the number of the main chain C it’s attached to 4 3 1 2 3 4 5 6

68. Name the Alkene write the name in the following order 3–ethyl–
substituent number of first alphabetical substituent – substituent name of first alphabetical substituent –
use prefixes to indicate multiple identical substituents
repeat for other substituents
number of first C in double bond – name of main chain 4 3
3–ethyl–
4–methyl–
2–hexene 1 2 3 4 5 6

69. Practice – Name the Following

70. Practice – Name the Following3 4 5 6 2 1
3,4-dimethyl-3-hexene

71. Chapter 22: Organic Chemistry
4/17/2017
Alkenes and Alkynes
Alkenes
Ethylene and propylene are actually the common names but are now accepted IUPAC names.
-ene suffix since they are alkenes
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72. Chapter 22: Organic Chemistry
4/17/2017
Alkenes and Alkynes
Alkenes and Isomers
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73. Chapter 22: Organic Chemistry
4/17/2017
Alkenes and Alkynes
Alkenes and Isomers
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74. Chapter 22: Organic Chemistry
4/17/2017
Alkenes and Alkynes
Alkenes and Isomers
Copyright © 2010 Pearson Prentice Hall, Inc.

75. Chapter 22: Organic Chemistry
4/17/2017
Alkenes and Alkynes
Alkynes
-yne suffix since they are alkynes
Acetylene is the common name for ethyne which can be confusing because of the “ene” in acetylene.
No cis-trans isomerism in alkynes due to the 180° bond angle.
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76. Examples of Naming Alkynes
H H H
H C C C C C H
CH3 H H
3-methyl-1-pentyne
H CH3 H H
H C C C C C C H
H CH3 CH H
CH3 CH3
4-isopropyl-5,5-dimethyl-2-hexyne

77. Name the Alkyne
find the longest, continuous C chain that contains the triple bond and use it to determine the base name
since the longest chain with the triple bond has 7 C
the base name is heptyne

78. Name the Alkyne identify the substituent branches
there are 2 substituents
one is a 1 C chain, called methyl
the other one is called isopropyl

79. Name the Alkyne
number the chain from the end closest to the triple bond
then assign numbers to each substituent based
on the number of the main chain C it’s attached to 1 2 3 4 5 6 7 4 6

80. Name the Alkyne write the name in the following order 4–isopropyl–
substituent number of first alphabetical substituent – substituent name of first alphabetical substituent –
use prefixes to indicate multiple identical substituents
repeat for other substituents
number of first C in double bond – name of main chain 1 2 3 4 5 6 7 4 6
4–isopropyl–
6–methyl–
2–heptyne

81. Practice – Name the Following

82. Practice – Name the Following3 2 1 4 5
3,3-dimethyl-1-pentyne

83. Chapter 22: Organic Chemistry
4/17/2017
Reactions of Alkenes
Addition of Hydrogen:
This section title in the book is actually “Reactions of Alkenes and Alkynes” but they only cover alkenes which is why I’ve shortened this section title.
The second hydrogen addition is an example of hydrogenation.
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84. Chapter 22: Organic Chemistry
4/17/2017
Reactions of Alkenes
Copyright © 2010 Pearson Prentice Hall, Inc.

85. Chapter 22: Organic Chemistry
4/17/2017
Reactions of Alkenes
Addition of Cl2 and Br2:
The addition of water and halohalogens follows Markovnikov’s rule (not covered here).
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86. Chapter 22: Organic Chemistry
4/17/2017
Reactions of Alkenes
Addition of Water:
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87. Resonance Hybrid
the true structure of benzene is a resonance hybrid of two structures

88. Naming Monosubstituted Benzene Derivatives
(name of substituent)benzene
halogen substituent = change ending to “o”
fluorobenzene
propylbenzene
or name of a common derivative

89. Naming Benzene as a Substituent
when the benzene ring is not the base name, it is called a phenyl group
4-phenyl-1-hexene

90. Naming Disubstituted Benzene Derivatives
number the ring starting at attachment for first substituent, then move toward second
order substituents alphabetically
use “di” if both substituents the same 1 2 3
1-bromo-3-fluorobenzene 1 2
1,2-dimethylbenzene

91. Naming Disubstituted Benzene Derivatives
alternatively, use relative position prefix
ortho- = 1,2; meta- = 1,3; para- = 1,4
2-chlorotoluene
ortho-chlorotoluene
o-chlorotoluene
3-chlorotoluene
meta-chlorotoluene
m-chlorotoluene
4-chlorotoluene
para-chlorotoluene
p-chlorotoluene

92. Practice – Name the Following

93. Practice – Name the Following
1-chloro-4-fluorobenzene
1,3-dibromobenzene
or meta-dibromobenzene
or m-dibromobenzene

94. Aromatic Compounds and Their Reactions
Chapter 22: Organic Chemistry
4/17/2017
Aromatic Compounds and Their Reactions
Aromatic: A class of compounds that contain a six-membered ring with three double bonds.
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95. Aromatic Compounds and Their Reactions
Chapter 22: Organic Chemistry
4/17/2017
Aromatic Compounds and Their Reactions
The stability of benzene comes from its six pi-bond electrons which are spread equally around the entire ring:
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96. Aromatic Compounds and Their Reactions
Chapter 22: Organic Chemistry
4/17/2017
Aromatic Compounds and Their Reactions
Nitration (Substitution of a Nitro Group):
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97. Aromatic Compounds and Their Reactions
Chapter 22: Organic Chemistry
4/17/2017
Aromatic Compounds and Their Reactions
Halogenation (Substitution of a Bromine or Chlorine):
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98. Alcohols, Ethers, and Amines
Chapter 22: Organic Chemistry
4/17/2017
Alcohols, Ethers, and Amines
Alcohols: A class of compounds that contain a hydroxyl group (-OH).
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99. Alcohols, Ethers, and Amines
Chapter 22: Organic Chemistry
4/17/2017
Alcohols, Ethers, and Amines
Alcohols
Simple alcohols are often soluble in water because of hydrogen bonding:
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100. Alcohols, Ethers, and Amines
Chapter 22: Organic Chemistry
4/17/2017
Alcohols, Ethers, and Amines
Alcohols
-ol suffix since they are alcohols
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101. Alcohols, Ethers, and Amines
Chapter 22: Organic Chemistry
4/17/2017
Alcohols, Ethers, and Amines
Alcohols
Some important alcohols:
Top one is methanol.
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102. Alcohols, Ethers, and Amines
Chapter 22: Organic Chemistry
4/17/2017
Alcohols, Ethers, and Amines
Alcohols
Some important alcohols:
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103. Alcohols, Ethers, and Amines
Chapter 22: Organic Chemistry
4/17/2017
Alcohols, Ethers, and Amines
Alcohols
Some important alcohols:
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104. Alcohols, Ethers, and Amines
Chapter 22: Organic Chemistry
4/17/2017
Alcohols, Ethers, and Amines
Ethers
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105. Alcohols, Ethers, and Amines
Chapter 22: Organic Chemistry
4/17/2017
Alcohols, Ethers, and Amines
Amines
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106. Alcohols, Ethers, and Amines
Chapter 22: Organic Chemistry
4/17/2017
Alcohols, Ethers, and Amines
Amines
Base
Acid
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107. Chapter 22: Organic Chemistry
4/17/2017
Aldehydes and Ketones
Note the difference in polarities due to the atom(s) attached to the carbonyl group.
All have carbonyl groups
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108. Chapter 22: Organic Chemistry
4/17/2017
Aldehydes and Ketones
A hydrogen is bonded to a carbonyl in an aldehyde. The aldehyde is a terminal group. Notice the common names used, also.
A carbonyl between two carbons is a ketone, which is not a terminal group.
-al suffix since they are aldehydes
-one suffix since they are ketones
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109. Chapter 22: Organic Chemistry
4/17/2017
Aldehydes and Ketones
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110. Chapter 22: Organic Chemistry
4/17/2017
Aldehydes and Ketones
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111. Carboxylic Acids, Esters, and Amides
Chapter 22: Organic Chemistry
4/17/2017
Carboxylic Acids, Esters, and Amides
These are bonded to a strongly electronegative atom (O or N).
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112. Carboxylic Acids, Esters, and Amides
Chapter 22: Organic Chemistry
4/17/2017
Carboxylic Acids, Esters, and Amides
All three undergo carbonyl-substitution reactions:
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113. Carboxylic Acids, Esters, and Amides
Chapter 22: Organic Chemistry
4/17/2017
Carboxylic Acids, Esters, and Amides
Carboxylic Acids
Notice the ending: -oic acid.
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114. Carboxylic Acids, Esters, and Amides
Chapter 22: Organic Chemistry
4/17/2017
Carboxylic Acids, Esters, and Amides
Carboxylic Acids
They are weaker than their strong inorganic counterparts.
For acetic acid, Ka = 1.8 x 10-5 (pKa = 4.74)
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115. Carboxylic Acids, Esters, and Amides
Chapter 22: Organic Chemistry
4/17/2017
Carboxylic Acids, Esters, and Amides
Carboxylic Acids
A common industrial solvent.
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116. Carboxylic Acids, Esters, and Amides
Chapter 22: Organic Chemistry
4/17/2017
Carboxylic Acids, Esters, and Amides
Esters
Esters tend to be fragrant.
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117. Carboxylic Acids, Esters, and Amides
Chapter 22: Organic Chemistry
4/17/2017
Carboxylic Acids, Esters, and Amides
Esters
Hydrolysis:
Saponification (“soap”) is the base-catalyzed hydrolysis of naturally occurring esters in animal fat.
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118. Carboxylic Acids, Esters, and Amides
Chapter 22: Organic Chemistry
4/17/2017
Carboxylic Acids, Esters, and Amides
Amides
Even though both the amine and amide groups contain nitrogen, unlike the basic amine group, the amide group is neutral.
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119. Carboxylic Acids, Esters, and Amides
Chapter 22: Organic Chemistry
4/17/2017
Carboxylic Acids, Esters, and Amides
Amides
Hydrolysis:
This hydrolysis of amides is the key process that occurs in the stomach during digestion of proteins.
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120. Chapter 22: Organic Chemistry
4/17/2017
Synthetic Polymers
Polymers: Large molecules formed by the repetitive bonding of many smaller molecules, called monomers.
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121. Chapter 22: Organic Chemistry
4/17/2017
Synthetic Polymers
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122. Chapter 22: Organic Chemistry
4/17/2017
Synthetic Polymers
Polymerization:
Initiator
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123. Chapter 22: Organic Chemistry
4/17/2017
Synthetic Polymers
Polymerization:
Adipic acid can be found in apples.
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