Organic Chemistry
en.wikibooks.org
,August 9, 2015
On the 28th of April 2012 the contents of the English as well as German Wikibooks and Wikipedia
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compatible license, as stated in section 4b of the license. The list of contributors is included in chapter
Contributors on page 447. The licenses GPL, LGPL and GFDL are included in chapter Licenses on
page 471, since this book and/or parts of it may or may not be licensed under one or more of these
licenses, and thus require inclusion of these licenses. The licenses of the figures are given in the list of
figures on page 457. This PDF was generated by the LATEX typesetting software. The LATEX source
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,Contents
0.1 The Study of Organic Chemistry . . . . . . . . . . . . . . . . . . . . . . 2
1 Authors 5
2 Foreword 7
2.1 Purpose and mission . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
2.2 Content and Contributions . . . . . . . . . . . . . . . . . . . . . . . . . 7
2.3 Licensing . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8
2.4 How to study organic chemistry . . . . . . . . . . . . . . . . . . . . . . 8
3 Unit 1: Foundational concepts of organic chemistry 11
4 History of organic chemistry 13
4.1 Brief History . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
4.2 Synthesis of Urea . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
4.3 Organic vs Inorganic Chemistry . . . . . . . . . . . . . . . . . . . . . . 14
4.4 Major Advances in the Field of Organic Chemistry . . . . . . . . . . . . 14
5 Atomic structure 17
5.1 Atomic Structure . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17
5.2 Shells and Orbitals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18
5.3 Filling electron shells . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
5.4 Octet rule . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
5.5 Hybridization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
6 Electronegativity 23
7 Electronegativity content from Wikipedia 25
7.1 Pauling scale . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 25
7.2 Mulliken scale . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 25
7.3 Electronegativity trends . . . . . . . . . . . . . . . . . . . . . . . . . . . 26
8 Bonding 33
8.1 Ionic Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33
8.2 Covalent Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 34
8.3 Bond Polarity and Dipole Moment . . . . . . . . . . . . . . . . . . . . . 36
8.4 Van der Waals Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . 37
8.5 Organometallic Compounds and Bonding . . . . . . . . . . . . . . . . . 37
9 Electron dot structures & formal charge 39
9.1 Electron Dot Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
9.2 Formal Charge . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42
III
, Contents
10 Resonance 45
10.1 Resonance . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 45
10.2 Resonance Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46
10.3 Key characteristics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47
10.4 What resonance is not . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48
10.5 History . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48
10.6 Examples . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
10.7 See also . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
10.8 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
11 Acids and bases 51
11.1 Arrhenius Definition: Hydroxide and Hydronium Ions . . . . . . . . . . 51
11.2 Brønsted-Lowry Acids and Bases: Proton donors and acceptors . . . . . 51
11.3 Lewis Acids and Bases: Electron donors and acceptors . . . . . . . . . . 52
11.4 Nucleophiles and Electrophiles . . . . . . . . . . . . . . . . . . . . . . . 52
11.5 pKa and Acidity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53
12 Unit 2: Alkanes and cycloalkanes 55
13 Introduction 57
13.1 Introductory Definitions . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
13.2 Methane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
13.3 Ethane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59
14 Drawing alkanes 61
14.1 Line drawing shorthand . . . . . . . . . . . . . . . . . . . . . . . . . . . 61
15 Conformations 63
15.1 Newman projections . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 63
15.2 Conformations and energy . . . . . . . . . . . . . . . . . . . . . . . . . . 64
15.3 Steric effects . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64
15.4 Entropy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66
16 Preparation of Alkanes 67
17 Properties of Alkanes 71
17.1 Chemical properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 72
18 Introduction to Nomenclature 73
18.1 Number of hydrogens to carbons . . . . . . . . . . . . . . . . . . . . . . 73
18.2 Naming carbon chains up to twelve . . . . . . . . . . . . . . . . . . . . . 74
18.3 Isomerism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
18.4 Branched chains . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
18.5 Constitutional isomers . . . . . . . . . . . . . . . . . . . . . . . . . . . . 76
18.6 Naming Alkanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
18.7 IUPAC naming rules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
18.8 Branched Substituents . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82
18.9 Common system . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82
IV
en.wikibooks.org
,August 9, 2015
On the 28th of April 2012 the contents of the English as well as German Wikibooks and Wikipedia
projects were licensed under Creative Commons Attribution-ShareAlike 3.0 Unported license. A
URI to this license is given in the list of figures on page 457. If this document is a derived work
from the contents of one of these projects and the content was still licensed by the project under
this license at the time of derivation this document has to be licensed under the same, a similar or a
compatible license, as stated in section 4b of the license. The list of contributors is included in chapter
Contributors on page 447. The licenses GPL, LGPL and GFDL are included in chapter Licenses on
page 471, since this book and/or parts of it may or may not be licensed under one or more of these
licenses, and thus require inclusion of these licenses. The licenses of the figures are given in the list of
figures on page 457. This PDF was generated by the LATEX typesetting software. The LATEX source
code is included as an attachment (source.7z.txt) in this PDF file. To extract the source from
the PDF file, you can use the pdfdetach tool including in the poppler suite, or the http://www.
pdflabs.com/tools/pdftk-the-pdf-toolkit/ utility. Some PDF viewers may also let you save
the attachment to a file. After extracting it from the PDF file you have to rename it to source.7z.
To uncompress the resulting archive we recommend the use of http://www.7-zip.org/. The LATEX
source itself was generated by a program written by Dirk Hünniger, which is freely available under
an open source license from http://de.wikibooks.org/wiki/Benutzer:Dirk_Huenniger/wb2pdf.
,Contents
0.1 The Study of Organic Chemistry . . . . . . . . . . . . . . . . . . . . . . 2
1 Authors 5
2 Foreword 7
2.1 Purpose and mission . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
2.2 Content and Contributions . . . . . . . . . . . . . . . . . . . . . . . . . 7
2.3 Licensing . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8
2.4 How to study organic chemistry . . . . . . . . . . . . . . . . . . . . . . 8
3 Unit 1: Foundational concepts of organic chemistry 11
4 History of organic chemistry 13
4.1 Brief History . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
4.2 Synthesis of Urea . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
4.3 Organic vs Inorganic Chemistry . . . . . . . . . . . . . . . . . . . . . . 14
4.4 Major Advances in the Field of Organic Chemistry . . . . . . . . . . . . 14
5 Atomic structure 17
5.1 Atomic Structure . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17
5.2 Shells and Orbitals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18
5.3 Filling electron shells . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
5.4 Octet rule . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
5.5 Hybridization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
6 Electronegativity 23
7 Electronegativity content from Wikipedia 25
7.1 Pauling scale . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 25
7.2 Mulliken scale . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 25
7.3 Electronegativity trends . . . . . . . . . . . . . . . . . . . . . . . . . . . 26
8 Bonding 33
8.1 Ionic Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33
8.2 Covalent Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 34
8.3 Bond Polarity and Dipole Moment . . . . . . . . . . . . . . . . . . . . . 36
8.4 Van der Waals Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . 37
8.5 Organometallic Compounds and Bonding . . . . . . . . . . . . . . . . . 37
9 Electron dot structures & formal charge 39
9.1 Electron Dot Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
9.2 Formal Charge . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42
III
, Contents
10 Resonance 45
10.1 Resonance . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 45
10.2 Resonance Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46
10.3 Key characteristics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47
10.4 What resonance is not . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48
10.5 History . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48
10.6 Examples . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
10.7 See also . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
10.8 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
11 Acids and bases 51
11.1 Arrhenius Definition: Hydroxide and Hydronium Ions . . . . . . . . . . 51
11.2 Brønsted-Lowry Acids and Bases: Proton donors and acceptors . . . . . 51
11.3 Lewis Acids and Bases: Electron donors and acceptors . . . . . . . . . . 52
11.4 Nucleophiles and Electrophiles . . . . . . . . . . . . . . . . . . . . . . . 52
11.5 pKa and Acidity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53
12 Unit 2: Alkanes and cycloalkanes 55
13 Introduction 57
13.1 Introductory Definitions . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
13.2 Methane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
13.3 Ethane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59
14 Drawing alkanes 61
14.1 Line drawing shorthand . . . . . . . . . . . . . . . . . . . . . . . . . . . 61
15 Conformations 63
15.1 Newman projections . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 63
15.2 Conformations and energy . . . . . . . . . . . . . . . . . . . . . . . . . . 64
15.3 Steric effects . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64
15.4 Entropy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66
16 Preparation of Alkanes 67
17 Properties of Alkanes 71
17.1 Chemical properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 72
18 Introduction to Nomenclature 73
18.1 Number of hydrogens to carbons . . . . . . . . . . . . . . . . . . . . . . 73
18.2 Naming carbon chains up to twelve . . . . . . . . . . . . . . . . . . . . . 74
18.3 Isomerism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
18.4 Branched chains . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
18.5 Constitutional isomers . . . . . . . . . . . . . . . . . . . . . . . . . . . . 76
18.6 Naming Alkanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
18.7 IUPAC naming rules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
18.8 Branched Substituents . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82
18.9 Common system . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82
IV
