Alkanes 2-4 Straight-Chain and Branched Alkanes

1 2

2-5 Naming the Alkanes 2-5 Naming the Alkanes

3 4
 2-5 Naming the Alkanes Naming the Alkanes: IUPAC Rules

5 6

Naming the Alkanes: IUPAC Rules Naming the Alkanes: IUPAC Rules

7 8
Naming the Alkanes: IUPAC Rules Naming the Alkanes: IUPAC Rules

IUPAC Rule 4. Write the name of the alkane by first arranging all the
substituents in alphabetical order (each preceded by the carbon number to
which it is attached and a hyphen) and then adding the name of the stem.

9 10

11
Naming the Alkanes: IUPAC RUles 2-6 Structural and Physical Properties of Alkanes

12
Physical Properties of Alkanes: Attractive Forces 2-7 Rotation about Single Bonds: Conformations of Ethane

13 14

Conformations of Ethane: Newman Projections Conformations of Ethane: Potential Energies

15 16
2-8 Rotation in Substituted Ethanes: Steric Hindrance Conformation Analysis of Butane

17 18

Conformation Analysis of Butane Conformation Analysis: Substituted Ethanes

<= Very important interaction!!!

19 20
Conformation Analysis: Rotational Barriers Problems

21 22

Problems Problems

23 24
 3-1 Strength of Alkane Bonds: Radicals Formation of Radicals: Homolytic Cleavage

25 26

Formation of Radicals: Homolytic Cleavage Formation of Radicals: Homolytic Cleavage

27 28
 30
Formation of Radicals: Homolytic Cleavage Formation of Radicals: Homolytic Cleavage

29

The Stability of Radicals: the C–H Bond Strengths The Stability of Radicals: the C–H Bond Strengths

31 32
 3-2 Structural of Alkyl Radicals: Hyperconjugation 3-2 Structural of Alkyl Radicals: Hyperconjugation

33 34

3-3 Conversion of Petroleum: Pyrolysis-Bond Homolysis 3-3 Conversion of Petroleum: Pyrolysis-Bond Homolysis

35 36
 Conversion of Petroleum: The Function of Catalyst 3-4 Chlorination of Methane: The Radical Chain Mechanism

37 38

3-4 Chlorination of Methane: The Radical Chain Mechanism 3-4 Chlorination of Methane: The Radical Chain Mechanism

39 40
3-4 Chlorination of Methane: The Radical Chain Mechanism 3-4 Chlorination of Methane: The Radical Chain Mechanism

Potential-energy diagram of the rxn of CH4 and Cl atom

41 42

3-4 Chlorination of Methane: The Radical Chain Mechanism 3-4 Chlorination of Methane: The Radical Chain Mechanism

43 44
3-4 Chlorination of Methane: The Radical Chain Mechanism 3-5 Other Radical Halogenation of Methane

45 46

47
3-5 Other Radical Halogenation of Methane 3-6 Chlorination of Higher Alkanes: Reactivity and Selectivity

48
 49 50
Chlorination of Higher Alkanes: Propane Chlorination of Higher Alkanes: Propane

Chlorination of Higher Alkanes: 2-Methylpropane Chlorination of Higher Alkanes: Butane

51 52
3-7 Halogenation with Fluorine and Bromine: Selectivity Fluorination of 2-Methylpropane: Selectivity

Figure 3-10 Potential-energy diagram for the abstraction of a primary or a tertiary

hydrogen by a fl uorine atom from 2-methylpropane. The energies of the respective
early transition states are almost the same and barely higher than that of starting
53 material (i.e., both Ea values are close to zero), resulting in little selectivity. 54

Bromination of 2-Methylpropane: Selectivity Bromination of 2-Methylpropane: Selectivity

Figure 3-11 Potential-energy diagram for the abstraction of a primary or a tertiary

hydrogen of 2-methylpropane by a bromine atom. The two late transition states are
dissimilar in energy, indicative of the energy difference between the resulting primary
55
and tertiary radicals, respectively, leading with greater selectivity to the products. 56
 3-8 Synthetic Radical Halogenation 3-8 Synthetic Radical Halogenation

+ Fluorine is expensive and corrosive. Fluorinations are often violently

uncontrollable

+ Iodination fail because of unfavorable thermodynamics.

+ Chlorinations are important, particularly in industry. 57 58

3-8 Synthetic Radical Halogenation 3-9 Synthetic Chlorine Compounds and the Stratospheric
Ozone Layer

59 60
 61 62
3-9 Synthetic Chlorine Compounds and the Stratospheric 3-9 Synthetic Chlorine Compounds and the Stratospheric
Ozone Layer Ozone Layer

3-9 Synthetic Chlorine Compounds and the Stratospheric 3-10 Combustion and the Relative Stabilities of Alkanes
Ozone Layer

63 64
3-10 Combustion and the Relative Stabilities of Alkanes 3-10 Combustion and the Relative Stabilities of Alkanes

65 66

Cycloalkanes 4-1 Names and Physical Properties of Cycloalkanes

67 68
Names and Physical Properties of Cycloalkanes Names and Physical Properties of Cycloalkanes

69 70

Names and Physical Properties of Cycloalkanes Names of Cycloalkanes: Disubstituted Ones

71 72
 Names of Cycloalkanes: Disubstituted Ones 4-2 Ring Strain and the Structure of Cycloalkanes: ∆Hocomb

73 74

75
4-2 Ring Strain and the Structure of Cycloalkanes: ∆Hocomb Strain Affects the Structure and Confirmation of Small Rings

76
Strain Affects the Structure and Confirmation of Small Rings Strain Affects the Structure and Confirmation of Small Rings

77 78

80
Strain Affects the Structure and Confirmation of Small Rings 4-3 Cyclohexane: A Strain-Free Cycloalkene

79
 81
Cyclohexane: A Strain-Free Cycloalkene Cyclohexane: Less stable Conformation

82

Cyclohexane: Axial and Equatorial Hydrogen Atoms Cyclohexane: Axial and Equatorial Hydrogen Atoms

83 84
Draw Cyclohexane with Axial and Equatorial Hydrogen Atoms Draw Cyclohexane with Axial and Equatorial Hydrogen Atoms

85 86

4-4 Substituted Cyclohexane Substituted Cyclohexane: 1,3-Diaxial Interaction

87 88
Substituted Cyclohexane: 1,3-Diaxial Interaction Substituted Cyclohexane: 1,3-Diaxial Interaction

89 90

Substituted Cyclohexane: 1,3-Diaxial Interaction Substituted Cyclohexane: Compete for Equatorial Positions

91 92
Substituted Cyclohexane: Compete for Equatorial Positions Substituted Cyclohexane: Conformational Analysis

93 94

Substituted Cyclohexane: Conformational Analysis Substituted Cyclohexane: Conformational Analysis

95 96
Substituted Cyclohexane: Conformational Analysis Substituted Cyclohexane: Conformational Analysis

97 98

Substituted Cyclohexane: Conformational Analysis Substituted Cyclohexane: Conformational Analysis

99 100
Substituted Cyclohexane: Conformational Analysis Cyclohexene: Conformational Analysis

101 102

Cyclohexene: Conformational Analysis Substituted Cyclohexane: Compete for Equatorial Positions

103 104
 105
4-6 Polycyclic Alkanes Fused Ring: Cis- and Trans- Configurations

106

Fused Ring: Conformational Analysis Fused Ring: Conformational Analysis

107 108
 Fused Ring: Strain 4-7 Carbocyclic Products in Nature: Terpenes

109 110

Carbocyclic Products in Nature: Terpenes Carbocyclic Products in Nature: Steroids

111 112
Cholesterol: How Is It and How Bad Is It? Carbocyclic Products in Nature: Steroids

113 114

Chapter Intergration Problems Chapter Intergration Problems

115 116
Chapter Intergration Problems Chapter Intergration Problems

117 118

Chapter Intergration Problems

119