Organic Chemistry II-OER

Course Modules

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Context Module Sub Header

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License. 1

context_module_sub_header 156550 0

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Syllabus

Syllabus Syllabus

Attachment

SyllChem2242019-2.doc SyllChem2242019-2.doc 1

attachment 157532 0

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15: Ethers, Epoxides and Thioethers

15: Ethers, Epoxides and Thioethers 15: Ethers, Epoxides and Thioethers

Page

Importance of Ethers Importance of Ethers 1

wiki_page 156239 0

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External Url

Khan Academy-Ethers Khan Academy-Ethers 2

external_url 156240 0

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Page

The attribute for the content utilized for this course that was published by Wade is CC BY-NC-SA 4.0. The attribute for the content utilized for this course that was published by Wade is CC BY-NC-SA 4.0. 3

wiki_page 156241 0

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External Url

Naming Ethers, Epoxides and Sulfides Naming Ethers, Epoxides and Sulfides 4

external_url 156242 0

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Attachment

Naming Ethers,_Epoxides_and_Sulfides Naming Ethers,_Epoxides_and_Sulfides 5

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External Url

15.1: Physical Properties of Ethers 15.1: Physical Properties of Ethers 6

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External Url

15.2: Spectroscopy of Ethers 15.2: Spectroscopy of Ethers 7

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External Url

15.3: The Williamson Ether Synthesis 15.3: The Williamson Ether Synthesis 8

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External Url

15.4: Alkoxymercuration-Demercuration Synthesis of Ethers 15.4: Alkoxymercuration-Demercuration Synthesis of Ethers 9

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External Url

15.5: Acidic Cleavage of Ethers 15.5: Acidic Cleavage of Ethers 10

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External Url

15.6: Autoxidation of Ethers 15.6: Autoxidation of Ethers 11

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External Url

15.7: Synthesis of Epoxides 15.7: Synthesis of Epoxides 12

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External Url

15.8: Opening of Epoxides 15.8: Opening of Epoxides 13

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External Url

15.09: Reactions of Epoxides with Grignard and Organolithium Reagents 15.09: Reactions of Epoxides with Grignard and Organolithium Reagents 14

external_url 156252 0

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External Url

15.10: Crown Ethers 15.10: Crown Ethers 15

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External Url

15.11: Epoxy Resins: The Advent of Modern Glues 15.11: Epoxy Resins: The Advent of Modern Glues 16

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External Url

15.12: Thioethers (Sulfides) and Silyl Ethers 15.12: Thioethers (Sulfides) and Silyl Ethers 17

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16: Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy-The attribute for the content utilized for this course that was published by Wade is CC BY-NC-SA 4.0.

16: Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy-The attribute for the content utilized for this course that was published by Wade is CC BY-NC-SA 4.0. 16: Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy-The attribute for the content utilized for this course that was published by Wade is CC BY-NC-SA 4.0.

External Url

16.1: Stability of Conjugated Dienes - Molecular Orbital Theory 16.1: Stability of Conjugated Dienes - Molecular Orbital Theory 1

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External Url

16.2: Allylic Cations 16.2: Allylic Cations 2

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External Url

16.3: Electrophilic Additions to Conjugated Dienes 16.3: Electrophilic Additions to Conjugated Dienes 3

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External Url

16.4: Kinetic versus Thermodynamic Control 16.4: Kinetic versus Thermodynamic Control 4

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External Url

16.5: SN2 Reactions of Allylic Halides and Tosylates 16.5: SN2 Reactions of Allylic Halides and Tosylates 5

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External Url

16.6: The Diels-Alder (4 + 2) Cycloaddition Reaction 16.6: The Diels-Alder (4 + 2) Cycloaddition Reaction 6

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External Url

16.7: Diels-Alder Stereochemistry 16.7: Diels-Alder Stereochemistry 7

external_url 156262 0

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External Url

16.8: Diene Polymers - Natural and Synthetic Rubbers 16.8: Diene Polymers - Natural and Synthetic Rubbers 8

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External Url

16.09: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy 16.09: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy 9

external_url 156264 0

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External Url

16.10: Interpreting Ultraviolet Spectra - The Effect of Conjugation 16.10: Interpreting Ultraviolet Spectra - The Effect of Conjugation 10

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16.11:Conjugation, Color, and the Chemistry of Vision 16.11:Conjugation, Color, and the Chemistry of Vision 11

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17: Aromatic Compounds

17: Aromatic Compounds 17: Aromatic Compounds

Page

Importance of Aromatic Compounds Importance of Aromatic Compounds 1

wiki_page 156267 0

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External Url

Khan Academy-Aromatic Compounds Khan Academy-Aromatic Compounds 2

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Page

CC BY-NC-SA 4.0----content attribute CC BY-NC-SA 4.0----content attribute 3

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External Url

17.1: Introduction: The Discovery of Benzene 17.1: Introduction: The Discovery of Benzene 4

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External Url

17.2: The Structure and Properties of Benzene and its Derivatives 17.2: The Structure and Properties of Benzene and its Derivatives 5

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External Url

17.3: Resonance and the Molecular Orbitals of Benzene 17.3: Resonance and the Molecular Orbitals of Benzene 6

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17.4: The Molecular Orbital Picture of Cyclobutadiene 17.4: The Molecular Orbital Picture of Cyclobutadiene 7

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External Url

17.5: Aromaticity and Huckel's Rule 17.5: Aromaticity and Huckel's Rule 8

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External Url

17.6: Aromatic Ions - a closer look 17.6: Aromatic Ions - a closer look 9

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External Url

17.7: Heterocyclic Aromatic Compounds - a closer look 17.7: Heterocyclic Aromatic Compounds - a closer look 10

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External Url

17.8: Polycyclic Aromatic Hydrocarbons 17.8: Polycyclic Aromatic Hydrocarbons 11

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External Url

17.9: Spectroscopy of Aromatic Compounds 17.9: Spectroscopy of Aromatic Compounds 12

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External Url

Naming of Benzene and its Derivatives Naming of Benzene and its Derivatives 13

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18: Reactions of Aromatic Compounds-The attribute for the content utilized for this course that was published by Wade is CC BY-NC-SA 4.0.

18: Reactions of Aromatic Compounds-The attribute for the content utilized for this course that was published by Wade is CC BY-NC-SA 4.0. 18: Reactions of Aromatic Compounds-The attribute for the content utilized for this course that was published by Wade is CC BY-NC-SA 4.0.

Page

CC BY-NC-SA 4.0----content attribute CC BY-NC-SA 4.0----content attribute 1

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External Url

17.1: Electrophilic Aromatic Substitution 17.1: Electrophilic Aromatic Substitution 2

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External Url

17.2: Halogenation of Benzene 17.2: Halogenation of Benzene 3

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External Url

17.3: Nitration of Benzene 17.3: Nitration of Benzene 4

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External Url

17.4: Sulfonation of Benzene 17.4: Sulfonation of Benzene 5

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External Url

17.5: Nitration of Toluene: The Effect of Alkyl Substitution 17.5: Nitration of Toluene: The Effect of Alkyl Substitution 6

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17.6: Activating, Ortho, Para-Directing Substituents 17.6: Activating, Ortho, Para-Directing Substituents 7

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17.7: Deactivating, Meta-Directing Substituents 17.7: Deactivating, Meta-Directing Substituents 8

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External Url

17.8: Halogen Substituents: Deactivating, but Ortho, Para-Directing 17.8: Halogen Substituents: Deactivating, but Ortho, Para-Directing 9

external_url 156288 0

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17.9: Effects of Multiple Substituents on Electrophilic Aromatic Substitution 17.9: Effects of Multiple Substituents on Electrophilic Aromatic Substitution 10

external_url 156289 0

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External Url

17.10: The Friedel-Crafts Alkylation 17.10: The Friedel-Crafts Alkylation 11

external_url 156290 0

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External Url

17.11: The Friedel-Crafts Acylation 17.11: The Friedel-Crafts Acylation 12

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External Url

17.12: Nucleophilic Aromatic Substitution 17.12: Nucleophilic Aromatic Substitution 13

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External Url

17.13: Aromatic Substitutions Using Organometallic Reagents 17.13: Aromatic Substitutions Using Organometallic Reagents 14

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External Url

17.14: Addition Reactions of Benzene Derivatives 17.14: Addition Reactions of Benzene Derivatives 15

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External Url

17.15: Side-Chain Reactions of Benzene Derivatives 17.15: Side-Chain Reactions of Benzene Derivatives 16

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External Url

17.16: Reactions of Phenols 17.16: Reactions of Phenols 17

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19: Ketones and Aldehydes

19: Ketones and Aldehydes 19: Ketones and Aldehydes

Page

Importance of Aldehydes & Ketones Importance of Aldehydes & Ketones 1

wiki_page 156297 0

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External Url

Importance of Aldehydes Continued Importance of Aldehydes Continued 2

external_url 156298 0

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Page

CC BY-NC-SA 4.0----content attribute CC BY-NC-SA 4.0----content attribute 3

wiki_page 156299 0

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External Url

18.1: Carbonyl Compounds 18.1: Carbonyl Compounds 4

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18.2: Structure of the Carbonyl Group 18.2: Structure of the Carbonyl Group 5

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External Url

Naming Aldehydes and Ketones Naming Aldehydes and Ketones 6

external_url 156302 0

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External Url

18.3: Nomenclature of Ketones and Aldehydes 18.3: Nomenclature of Ketones and Aldehydes 7

external_url 156303 0

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External Url

18.4: Physical Properties of Ketones and Aldehydes 18.4: Physical Properties of Ketones and Aldehydes 8

external_url 156304 0

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External Url

18.5: Spectroscopy of Ketones and Aldehydes 18.5: Spectroscopy of Ketones and Aldehydes 9

external_url 156305 0

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18.6: Industrial Importance of Ketones and Aldehydes 18.6: Industrial Importance of Ketones and Aldehydes 10

external_url 156306 0

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External Url

18.7: Review of Syntheses of Ketones and Aldehydes 18.7: Review of Syntheses of Ketones and Aldehydes 11

external_url 156307 0

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External Url

18.8 Synthesis of Ketones from Carboxylic Acids 18.9: Synthesis of Ketones and Aldehydes from Nitriles 18.8 Synthesis of Ketones from Carboxylic Acids 18.9: Synthesis of Ketones and Aldehydes from Nitriles 12

external_url 156308 0

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18.10: Synthesis of Aldehydes and Ketones from Acid Chlorides and Esters 18.10: Synthesis of Aldehydes and Ketones from Acid Chlorides and Esters 13

external_url 156309 0

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18.11: Reactions of Ketones and Aldehydes: Nucleophilic Addition 18.11: Reactions of Ketones and Aldehydes: Nucleophilic Addition 14

external_url 156310 0

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External Url

18.12: The Wittig Reaction 18.12: The Wittig Reaction 15

external_url 156311 0

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External Url

18.13: Hydration of Ketones and Aldehydes 18.13: Hydration of Ketones and Aldehydes 16

external_url 156312 0

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18.14: Formation of Cyanohydrins 18.14: Formation of Cyanohydrins 17

external_url 156313 0

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External Url

18.15: Formation of Imines 18.15: Formation of Imines 18

external_url 156314 0

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18.16: Condensations with Hydroxylamine and Hydrazines 18.16: Condensations with Hydroxylamine and Hydrazines 19

external_url 156315 0

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18.17: Formation of Acetals 18.17: Formation of Acetals 20

external_url 156316 0

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External Url

18.18: Use of Acetals as Protecting Groups 18.18: Use of Acetals as Protecting Groups 21

external_url 156317 0

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External Url

18.19: Oxidation of Aldehydes 18.19: Oxidation of Aldehydes 22

external_url 156318 0

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18.20: Reductions of Ketones and Aldehydes 18.20: Reductions of Ketones and Aldehydes 23

external_url 156319 0

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20: Amines

20: Amines 20: Amines

Page

Importance of Amines Importance of Amines 1

wiki_page 156320 0

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External Url

Some Biological Important Amines Some Biological Important Amines 2

external_url 156321 0

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Page

CC BY-NC-SA 4.0----content attribute CC BY-NC-SA 4.0----content attribute 4

wiki_page 156323 0

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External Url

19.3: Structure of Amines 19.3: Structure of Amines 5

external_url 156324 0

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External Url

3.12 Amines - Classification and Nomenclature 3.12 Amines - Classification and Nomenclature 6

external_url 156325 0

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External Url

19.2: Nomenclature of Amines 19.2: Nomenclature of Amines 7

external_url 156326 0

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19.4: Physical Properties of Amines 19.4: Physical Properties of Amines 8

external_url 156327 0

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19.5: Basicity of Amines 19.5: Basicity of Amines 9

external_url 156328 0

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19.6: Effects on Amine Basicity 19.6: Effects on Amine Basicity 10

external_url 156329 0

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19.7: Salts of Amines 19.7: Salts of Amines 11

external_url 156330 0

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19.8: Spectroscopy of Amines 19.8: Spectroscopy of Amines 12

external_url 156331 0

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External Url

19.9: Reactions of Amines with Ketones and Aldehydes 19.9: Reactions of Amines with Ketones and Aldehydes 13

external_url 156332 0

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19.10: Aromatic Substitution of Arylamines and Pyridine 19.10: Aromatic Substitution of Arylamines and Pyridine 14

external_url 156333 0

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19.11: Alkylation of Amines by Alkyl Halides 19.11: Alkylation of Amines by Alkyl Halides 15

external_url 156334 0

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19.12: Acylation of Amines by Acid Chlorides 19.12: Acylation of Amines by Acid Chlorides 16

external_url 156335 0

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19.13: Formation of Sulfonamides 19.13: Formation of Sulfonamides 17

external_url 156336 0

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19.14: Amines as Leaving Groups: The Hofmann Elimination 19.14: Amines as Leaving Groups: The Hofmann Elimination 18

external_url 156337 0

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19.15: Oxidation of Amines; The Cope Elimination 19.15: Oxidation of Amines; The Cope Elimination 19

external_url 156338 0

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External Url

19.16: Reactions of Amines with Nitrous Acid 19.16: Reactions of Amines with Nitrous Acid 20

external_url 156339 0

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External Url

19.17: Reactions of Arenediazonium Salts 19.17: Reactions of Arenediazonium Salts 21

external_url 156340 0

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19.18: Synthesis of Amines by Reductive Amination 19.18: Synthesis of Amines by Reductive Amination 22

external_url 156341 0

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External Url

19.19: Synthesis of Amines by Acylation-Reduction 19.19: Synthesis of Amines by Acylation-Reduction 23

external_url 156342 0

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19.20: Syntheses Limited to Primary Amines 19.20: Syntheses Limited to Primary Amines 24

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21: Carboxylic Acids

21: Carboxylic Acids 21: Carboxylic Acids

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CC BY-NC-SA 4.0----content attribute CC BY-NC-SA 4.0----content attribute 2

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Naming Carboxylic Acids Naming Carboxylic Acids 3

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20.2: Nomenclature of Carboxylic Acids 20.2: Nomenclature of Carboxylic Acids 4

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20.3: Structure and Physical Properties of Carboxylic Acids 20.3: Structure and Physical Properties of Carboxylic Acids 5

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20.4: Acidity of Carboxylic Acids 20.4: Acidity of Carboxylic Acids 6

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20.5: Salts of Carboxylic Acids 20.5: Salts of Carboxylic Acids 7

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20.6: Commercial Sources of Carboxylic Acids 20.6: Commercial Sources of Carboxylic Acids 8

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20.7: Spectroscopy of Carboxylic Acids 20.7: Spectroscopy of Carboxylic Acids 9

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20.8: Synthesis of Carboxylic Acids 20.8: Synthesis of Carboxylic Acids 10

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20.9: Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution 20.9: Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution 11

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20.10: Condensation of Acids with Alcohols: The Fischer Esterification 20.10: Condensation of Acids with Alcohols: The Fischer Esterification 12

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20.11: Esterification Using Diazomethane 20.11: Esterification Using Diazomethane 13

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20.12: Condensation of Acids with Amines: Direct Synthesis of Amides 20.12: Condensation of Acids with Amines: Direct Synthesis of Amides 14

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20.13: Reduction of Carboxylic Acids 20.13: Reduction of Carboxylic Acids 15

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20.14: Alkylation of Carboxylic Acids to Form Ketones 20.14: Alkylation of Carboxylic Acids to Form Ketones 16

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20.15: Synthesis and Use of Acid Chlorides 20.15: Synthesis and Use of Acid Chlorides 17

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22: Carboxylic Acid Derivatives

22: Carboxylic Acid Derivatives 22: Carboxylic Acid Derivatives

Page

Importance of Carboxylic Acid Derivatives Importance of Carboxylic Acid Derivatives 1

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Page

CC BY-NC-SA 4.0----content attribute CC BY-NC-SA 4.0----content attribute 2

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Nomenclature of Acid Derivatives Nomenclature of Acid Derivatives 3

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Naming Carboxylic Acid Derivatives Naming Carboxylic Acid Derivatives 4

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21.3: Physical Properties of Carboxylic Acid Derivatives 21.3: Physical Properties of Carboxylic Acid Derivatives 5

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21.4: Spectroscopy of Carboxylic Acid Derivatives 21.4: Spectroscopy of Carboxylic Acid Derivatives 6

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21.5: Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution 21.5: Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution 7

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21.6: Transesterification 21.6: Transesterification 8

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21.7: Hydrolysis of Carboxylic Acid Derivatives 21.7: Hydrolysis of Carboxylic Acid Derivatives 9

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21.8: Reduction of Acid Derivatives 21.8: Reduction of Acid Derivatives 10

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21.9: Reactions of Acid Derivatives with Organometallic Reagents 21.9: Reactions of Acid Derivatives with Organometallic Reagents 11

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21.10: Summary of the Chemistry of Acid Chlorides 21.10: Summary of the Chemistry of Acid Chlorides 12

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21.11: Summary of the Chemistry of Anhydrides 21.11: Summary of the Chemistry of Anhydrides 13

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21.12: Summary of the Chemistry of Esters 21.12: Summary of the Chemistry of Esters 14

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21.13: Summary of the Chemistry of Amides 21.13: Summary of the Chemistry of Amides 15

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21.14: Summary of the Chemistry of Nitriles 21.14: Summary of the Chemistry of Nitriles 16

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21.15: Thioesters 21.15: Thioesters 17

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21.16: Esters and Amides of Carbonic Acid 21.16: Esters and Amides of Carbonic Acid 18

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23: Condensations and Alpha Substitutions of Carbonyl Compounds

23: Condensations and Alpha Substitutions of Carbonyl Compounds 23: Condensations and Alpha Substitutions of Carbonyl Compounds

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CC BY-NC-SA 4.0----content attribute CC BY-NC-SA 4.0----content attribute 1

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22.2: Enols and Enolate Ions 22.2: Enols and Enolate Ions 2

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22.3: Alkylation of Enolate Ions 22.3: Alkylation of Enolate Ions 3

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22.4: Formation and Alkylation of Enamines 22.4: Formation and Alkylation of Enamines 4

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22.5: Alpha Halogenation of Ketones 22.5: Alpha Halogenation of Ketones 5

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22.6: Bromination of Acids: The HVZ Reaction 22.6: Bromination of Acids: The HVZ Reaction 6

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22.7: The Aldol Condensation of Ketones and Aldehydes 22.7: The Aldol Condensation of Ketones and Aldehydes 7

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22.8: Dehydration of Aldol Products 22.8: Dehydration of Aldol Products 8

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22.9: Crossed Aldol Condensations 22.9: Crossed Aldol Condensations 9

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22.10: Aldol Cyclizations 22.10: Aldol Cyclizations 10

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22.11: Planning Syntheses Using Aldol Condensations 22.11: Planning Syntheses Using Aldol Condensations 11

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22.12: The Claisen Ester Condensation 22.12: The Claisen Ester Condensation 12

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22.13: The Dieckmann Condensation: A Claisen Cyclization 22.13: The Dieckmann Condensation: A Claisen Cyclization 13

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22.14: Crossed Claisen Condensations 22.14: Crossed Claisen Condensations 14

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22.15: Syntheses Using β-Dicarbonyl Compounds 22.15: Syntheses Using β-Dicarbonyl Compounds 15

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22.16: The Malonic Ester Synthesis 22.16: The Malonic Ester Synthesis 16

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22.17: The Acetoacetic Ester Synthesis 22.17: The Acetoacetic Ester Synthesis 17

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22.18: Conjugate Additions: The Michael Reaction 22.18: Conjugate Additions: The Michael Reaction 18

external_url 156396 0

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22.19: The Robinson Annulation 22.19: The Robinson Annulation 19

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24: Carbohydrates and Nucleic Acids

24: Carbohydrates and Nucleic Acids 24: Carbohydrates and Nucleic Acids

Page

CC BY-NC-SA 4.0----content attribute CC BY-NC-SA 4.0----content attribute 1

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External Url

23.2: Classification of Carbohydrates 23.2: Classification of Carbohydrates 2

external_url 156399 0

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23.3: Monosaccharides 23.3: Monosaccharides 3

external_url 156400 0

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23.4: Erythro and Threo Diastereomers 23.4: Erythro and Threo Diastereomers 4

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23.5: Epimers 23.5: Epimers 5

external_url 156402 0

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23.6: Cyclic Structures of Monosaccharides 23.6: Cyclic Structures of Monosaccharides 6

external_url 156403 0

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23.17: Disaccharides 23.17: Disaccharides 17

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23.18: Polysaccharides 23.18: Polysaccharides 18

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23.19: Nucleic Acids: Introduction 23.19: Nucleic Acids: Introduction 19

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23.20: Ribonucleosides and Ribonucleotides 23.20: Ribonucleosides and Ribonucleotides 20

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23.21: The Structure of RNA and DNA 23.21: The Structure of RNA and DNA 21

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25: Amino Acids, Peptides, and Proteins

25: Amino Acids, Peptides, and Proteins 25: Amino Acids, Peptides, and Proteins

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24.2: Structure and Stereochemistry of the Amino Acids 24.2: Structure and Stereochemistry of the Amino Acids 3

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External Url

24.3: Acid-Base Properties of Amino Acids 24.3: Acid-Base Properties of Amino Acids 4

external_url 156423 0

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24.8: Structure and Nomenclature of Peptides and Proteins 24.8: Structure and Nomenclature of Peptides and Proteins 9

external_url 156428 0

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24.9: Peptide Structure Determination 24.9: Peptide Structure Determination 10

external_url 156429 0

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24.10: Solution-Phase Peptide Synthesis 24.10: Solution-Phase Peptide Synthesis 11

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24.11: Solid-Phase Peptide Synthesis 24.11: Solid-Phase Peptide Synthesis 12

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24.12: Classification of Proteins 24.12: Classification of Proteins 13

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24.13: Levels of Protein Structure 24.13: Levels of Protein Structure 14

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24.14: Protein Denaturation 24.14: Protein Denaturation 15

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26: Lipids

26: Lipids 26: Lipids

External Url

25.2: Waxes 25.2: Waxes 1

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25.3: Trigylcerides 25.3: Trigylcerides 2

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25.4: Saponification of Fats and Oils; Soaps and Detergents 25.4: Saponification of Fats and Oils; Soaps and Detergents 3

external_url 156437 0

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25.5: Phospholipids 25.5: Phospholipids 4

external_url 156438 0

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25.6: Steroids 25.6: Steroids 5

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25.7: Prostaglandins 25.7: Prostaglandins 6

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27: Polymers

27: Polymers 27: Polymers

External Url

Khan Academy- Macromolecules (Polymers) Khan Academy- Macromolecules (Polymers) 1

external_url 156476 0

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Page

CC BY-NC-SA 4.0----content attribute CC BY-NC-SA 4.0----content attribute 2

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26.2: Addition Polymers 26.2: Addition Polymers 3

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26.3: Stereochemistry of Polymers 26.3: Stereochemistry of Polymers 4

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26.4: Stereochemical Control of Polymerization; Ziegler-Natta Catalysts 26.4: Stereochemical Control of Polymerization; Ziegler-Natta Catalysts 5

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26.5: Natural and Synthetic Rubbers 26.5: Natural and Synthetic Rubbers 6

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26.6: Copolymers of Two or More Monomers 26.6: Copolymers of Two or More Monomers 7

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26.7: Condensation Polymers 26.7: Condensation Polymers 8

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26.8: Polymer Structure and Properties 26.8: Polymer Structure and Properties 9

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Wade pdf- CCBY-NC-SA-4.0 Content Attribute

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organicchemistrywade_full.pdf organicchemistrywade_full.pdf 2

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Sodeberg Book- CC-BY-NC-SA 4.0 Attribute

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soderberrg.pdf- CC BY-NC-SA 4.0 Attribute soderberrg.pdf- CC BY-NC-SA 4.0 Attribute 1

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