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    Organic Chemistry Ch. 4-Alkanes & Cycloalkanes

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    Thanh thảo Trịnh
    This document summarizes Chapter 4 on alkanes and cycloalkanes from an organic chemistry textbook. The chapter covers nomenclature of alkanes including naming parent chains, substituents, and complex compounds. It also discusses constitutional isomers, relative stability of isomers, sources and uses of alkanes. Additionally, the chapter examines drawing Newman projections, conformational analysis of ethane, propane, butane and cycloalkanes. It provides examples of analyzing conformations and naming bicyclic and monocyclic compounds.

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    Organic Chemistry Ch. 4-Alkanes & Cycloalkanes

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    Thanh thảo Trịnh
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    This document summarizes Chapter 4 on alkanes and cycloalkanes from an organic chemistry textbook. The chapter covers nomenclature of alkanes including naming parent chains, substituents, and complex compounds. It also discusses constitutional isomers, relative stability of isomers, sources and uses of alkanes. Additionally, the chapter examines drawing Newman projections, conformational analysis of ethane, propane, butane and cycloalkanes. It provides examples of analyzing conformations and naming bicyclic and monocyclic compounds.

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    -Organic Chemistry Ch. 4-Alkanes & Cycloalkanes

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    This document summarizes Chapter 4 on alkanes and cycloalkanes from an organic chemistry textbook. The chapter covers nomenclature of alkanes including naming parent chains, substituents, and complex compounds. It also discusses constitutional isomers, relative stability of isomers, sources and uses of alkanes. Additionally, the chapter examines drawing Newman projections, conformational analysis of ethane, propane, butane and cycloalkanes. It provides examples of analyzing conformations and naming bicyclic and monocyclic compounds.

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    © All Rights Reserved
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    18 views40 pages

    Organic Chemistry Ch. 4-Alkanes & Cycloalkanes

    Uploaded by

    Thanh thảo Trịnh
    This document summarizes Chapter 4 on alkanes and cycloalkanes from an organic chemistry textbook. The chapter covers nomenclature of alkanes including naming parent chains, substituents, and complex compounds. It also discusses constitutional isomers, relative stability of isomers, sources and uses of alkanes. Additionally, the chapter examines drawing Newman projections, conformational analysis of ethane, propane, butane and cycloalkanes. It provides examples of analyzing conformations and naming bicyclic and monocyclic compounds.

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    of 40

    Hóa Hữu cơ 1

    TS. Huỳnh Ngọc Vinh

    hnvinh@hcmus.edu.vn

    Chapter 4: Alkanes and Cycloalkanes

    2
    Chapter 4: Alkanes and Cycloalkanes

    Chapter 4: Alkanes and Cycloalkanes


    4.1. Introduction to Alkanes

    4
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    An Introduction to IUPAC Nomenclature

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Selecting the Parent Chain

    6
    Chapter 4: Alkanes and Cycloalkanes

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Selecting the Parent Chain

    ¾ Identify and provide a name for the parent in the following compound

    8
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    Selecting the Parent Chain

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Naming Substituents

    10
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    Naming Substituents

    Number of Terminology
    Carbon Atoms
    in Substituent
    1 Methyl
    2 Ethyl
    3 Propyl
    4 Butyl
    5 Pentyl
    6 Hexyl
    7 Heptyl
    8 Octyl
    9 Nonyl
    10 decyl
    11

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Naming Substituents
    ¾ Identify and and name all substituents in the following compound

    12
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    Naming Complex Substituents

    13

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Naming Complex Substituents

    14
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    Naming Complex Substituents

    15

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Naming Complex Substituents

    ¾ In the following compound, identify all groups that would be


    considered substituents and then indicate the systematic name as well
    as the common name for each substituent

    16
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    Naming Complex Substituents

    17

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Assembling the Systematic Name of an Alkane

    18
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    Assembling the Systematic Name of an Alkane

    19

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Assembling the Systematic Name of an Alkane

    ¾ Provide a systematic name for the following compound

    20
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    Assembling the Systematic Name of an Alkane

    21

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Naming Bicyclic Compounds

    22
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    Naming Bicyclic Compounds

    23

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Naming Bicyclic Compounds

    24
    Chapter 4: Alkanes and Cycloalkanes
    4.2. Nomenclature of Alkanes
    Naming Bicyclic Compounds
    ¾ Assign a name for the following compound

    25

    Chapter 4: Alkanes and Cycloalkanes


    4.2. Nomenclature of Alkanes
    Naming Bicyclic Compounds

    2-Isopropyl-7,7-dimethylbicyclo[3.2.0]heptane 26
    Chapter 4: Alkanes and Cycloalkanes
    4.3. Constitutional Isomers of Alkanes

    27

    Chapter 4: Alkanes and Cycloalkanes


    4.3. Constitutional Isomers of Alkanes

    28
    Chapter 4: Alkanes and Cycloalkanes
    4.3. Constitutional Isomers of Alkanes

    ¾ Identify whether the following two compounds are constitutional


    isomers or whether they are simply different drawings of the same
    compound

    29

    Chapter 4: Alkanes and Cycloalkanes


    4.3. Constitutional Isomers of Alkanes

    30
    Chapter 4: Alkanes and Cycloalkanes
    4.4. Relative Stability of Isomeric Alkanes

    31

    Chapter 4: Alkanes and Cycloalkanes


    4.4. Relative Stability of Isomeric Alkanes

    32
    Chapter 4: Alkanes and Cycloalkanes
    4.5. Sources and Uses of Alkanes

    33

    Chapter 4: Alkanes and Cycloalkanes


    4.5. Sources and Uses of Alkanes

    34
    Chapter 4: Alkanes and Cycloalkanes
    4.6. Drawing Newman Projections

    35

    Chapter 4: Alkanes and Cycloalkanes


    4.6. Drawing Newman Projections
    ¾ Draw a Newman projection of the following compound, as view from
    the angle indicated

    36
    Chapter 4: Alkanes and Cycloalkanes
    4.6. Drawing Newman Projections

    37

    Chapter 4: Alkanes and Cycloalkanes


    4.6. Drawing Newman Projections

    38
    Chapter 4: Alkanes and Cycloalkanes
    4.7. Conformational Analysis of Ethane and Propane

    39

    Chapter 4: Alkanes and Cycloalkanes


    4.7. Conformational Analysis of Ethane and Propane

    40
    Chapter 4: Alkanes and Cycloalkanes
    4.7. Conformational Analysis of Ethane and Propane

    41

    Chapter 4: Alkanes and Cycloalkanes


    4.7. Conformational Analysis of Ethane and Propane

    42
    Chapter 4: Alkanes and Cycloalkanes
    4.7. Conformational Analysis of Ethane and Propane

    43

    Chapter 4: Alkanes and Cycloalkanes


    4.7. Conformational Analysis of Ethane and Propane

    44
    Chapter 4: Alkanes and Cycloalkanes
    4.8. Conformational Analysis of Butane

    45

    Chapter 4: Alkanes and Cycloalkanes


    4.8. Conformational Analysis of Butane

    46
    Chapter 4: Alkanes and Cycloalkanes
    4.8. Conformational Analysis of Butane

    47

    Chapter 4: Alkanes and Cycloalkanes


    4.8. Conformational Analysis of Butane

    48
    Chapter 4: Alkanes and Cycloalkanes
    4.8. Conformational Analysis of Butane

    49

    Chapter 4: Alkanes and Cycloalkanes


    4.8. Conformational Analysis of Butane
    ¾ Consider the following compound

    a) Rotating only the C3-C4 bond, identify the lowest energy conformation
    b) Rotating only the C3-C4 bond, identify the highest energy conformation

    50
    Chapter 4: Alkanes and Cycloalkanes
    4.8. Conformational Analysis of Butane

    51

    Chapter 4: Alkanes and Cycloalkanes


    4.9. Cycloalkanes

    52
    Chapter 4: Alkanes and Cycloalkanes
    4.9. Cycloalkanes

    53

    Chapter 4: Alkanes and Cycloalkanes


    4.9. Cycloalkanes

    54
    Chapter 4: Alkanes and Cycloalkanes
    4.9. Cycloalkanes
    Cyclopropane

    55

    Chapter 4: Alkanes and Cycloalkanes


    4.9. Cycloalkanes
    Cyclobutane

    Cyclopentane

    56
    Chapter 4: Alkanes and Cycloalkanes
    4.10. Conformations of Cyclohexane

    57

    Chapter 4: Alkanes and Cycloalkanes


    4.10. Conformations of Cyclohexane

    58
    Chapter 4: Alkanes and Cycloalkanes
    4.10. Conformations of Cyclohexane

    59

    Chapter 4: Alkanes and Cycloalkanes


    4.11. Drawing Chair Conformations
    Drawing the Skeleton of a Chair Conformation

    60
    Chapter 4: Alkanes and Cycloalkanes
    4.11. Drawing Chair Conformations
    Drawing the Skeleton of a Chair Conformation

    Drawing Axial and Equatorial Substituents

    61

    Chapter 4: Alkanes and Cycloalkanes


    4.11. Drawing Chair Conformations
    Drawing Axial and Equatorial Substituents
    ¾ Draw all axial and all equatorial positions on a chair conformation of
    cyclohexane

    62
    Chapter 4: Alkanes and Cycloalkanes
    4.12. Monosubstituted Cyclohexane
    Drawing Both Chair Conformations

    63

    Chapter 4: Alkanes and Cycloalkanes


    4.12. Monosubstituted Cyclohexane
    Drawing Both Chair Conformations
    ¾ Draw both chair conformations of bromocyclohexane

    64
    Chapter 4: Alkanes and Cycloalkanes
    4.12. Monosubstituted Cyclohexane
    Drawing Both Chair Conformations

    Comparing the Stability of Both Chair Conformations

    65

    Chapter 4: Alkanes and Cycloalkanes


    4.12. Monosubstituted Cyclohexane
    Comparing the Stability of Both Chair Conformations

    66
    Chapter 4: Alkanes and Cycloalkanes
    4.12. Monosubstituted Cyclohexane
    Comparing the Stability of Both Chair Conformations

    67

    Chapter 4: Alkanes and Cycloalkanes


    4.12. Monosubstituted Cyclohexane
    Comparing the Stability of Both Chair Conformations

    68
    Chapter 4: Alkanes and Cycloalkanes
    4.13. Disubstituted Cyclohexane
    Drawing Both Chair Conformations

    69

    Chapter 4: Alkanes and Cycloalkanes


    4.13. Disubstituted Cyclohexane
    Drawing Both Chair Conformations
    ¾ Draw both chair conformations of the following compound

    70
    Chapter 4: Alkanes and Cycloalkanes
    4.13. Disubstituted Cyclohexane
    Drawing Both Chair Conformations

    71

    Chapter 4: Alkanes and Cycloalkanes


    4.13. Disubstituted Cyclohexane
    Comparing the Stability of Chair Conformations

    72
    Chapter 4: Alkanes and Cycloalkanes
    4.13. Disubstituted Cyclohexane
    Comparing the Stability of Chair Conformations

    73

    Chapter 4: Alkanes and Cycloalkanes


    4.13. Disubstituted Cyclohexane
    Comparing the Stability of Chair Conformations

    ¾ Draw the more stable chair conformation of the following compound

    74
    Chapter 4: Alkanes and Cycloalkanes
    4.13. Disubstituted Cyclohexane
    Comparing the Stability of Chair Conformations

    75

    Chapter 4: Alkanes and Cycloalkanes


    4.13. Disubstituted Cyclohexane
    Comparing the Stability of Chair Conformations

    76
    Chapter 4: Alkanes and Cycloalkanes
    4.14. cis-trans Stereoisomerism

    77

    Chapter 4: Alkanes and Cycloalkanes


    4.15. Polycyclic Systems

    78
    Chapter 4: Alkanes and Cycloalkanes
    4.15. Polycyclic Systems

    79

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