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More About This Title Keynotes in Organic Chemistry 2e
English
This concise and accessible book provides organic chemistry notes for students studying chemistry and related courses at undergraduate level, covering core organic chemistry in a format ideal for learning and rapid revision. The material is organised so that fundamental concepts are introduced early, then built on to provide an overview of the essentials of functional group chemistry and reactivity, leading the student to a solid understanding of the basics of organic chemistry. Graphical presentation of information is central to the book, to facilitate the rapid assimilation, understanding and recall of critical concepts, facts and definitions.
Students wanting a comprehensive and accessible overview of organic chemistry to build the necessary foundations for a more detailed study will find this book an ideal source of the information they require. In addition, the structured presentation, highly graphical nature of the text and practice problems with outline answers will provide an invaluable framework and aid to revision for students preparing for examinations. Keynotes in Organic Chemistry is also a handy desk reference for advanced students, postgraduates and researchers.
For this second edition the text has been completely revised and updated. Colour has been introduced to clarify aspects of reaction mechanisms, and new margin notes to emphasise the links between different topics. The number of problems have been doubled to approximately 100, and includes spectra interpretation problems. Each chapter now starts with diagrams to illustrate the key points, and ends with a list of key reactions and a worked example.
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Dr Andrew Parsons, Department of Chemistry, University of York, UK
Dr Andrew Parsons is Deputy Head of the Department of Chemistry, University of York. His research interests cover radical approaches to the synthesis of biologically important heterocyclic compounds. He is the author/coauthor of Chemistry3: Introducing Inorganic, Organic and Physical chemistry, (OUP 2009), Keynotes in Organic Chemistry (Blackwell 2003) and An Introduction to Free Radical Chemistry (Blackwell 2000).
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Preface xi
1 Structure and bonding 1
1.1 Ionic versus covalent bonds 1
1.2 The octet rule 2
1.3 Formal charge 2
1.4 Sigma and pi bonds 3
1.5 Hybridisation 4
1.6 Inductive effects, hyperconjugation and mesomeric effects 6
1.7 Acidity and basicity 9
2 Functional groups, nomenclature and drawing organic compounds 21
2.1 Functional groups 21
2.2 Alkyl and aryl groups 22
2.3 Alkyl substitution 23
2.4 Naming carbon chains 23
2.5 Drawing organic structures 27
3 Stereochemistry 31
3.1 Isomerism 31
3.2 Conformational isomers 32
3.3 Configurational isomers 37
4 Reactivity and mechanism 49
4.1 Reactive intermediates: ions versus radicals 49
4.2 Nucleophiles and electrophiles 51
4.3 Carbocations, carbanions and carbon radicals 53
4.4 Steric effects 55
4.5 Oxidation levels 55
4.6 General types of reaction 56
4.7 Ions versus radicals 59
4.8 Reaction selectivity 60
4.9 Reaction thermodynamics and kinetics 60
4.10 Orbital overlap and energy 65
4.11 Guidelines for drawing reaction mechanisms 67
5 Halogenoalkanes 73
5.1 Structure 73
5.2 Preparation 74
5.3 Reactions 78
6 Alkenes and alkynes 95
6.1 Structure 95
6.2 Alkenes 97
6.3 Alkynes 110
7 Benzenes 117
7.1 Structure 117
7.2 Reactions 119
7.3 Reactivity of substituted benzenes 123
7.4 Nucleophilic aromatic substitution (the SNAr mechanism) 127
7.5 The formation of benzyne 128
7.6 Transformation of side chains 129
7.7 Reduction of the benzene ring 132
7.8 The synthesis of substituted benzenes 132
7.9 Electrophilic substitution of naphthalene 135
7.10 Electrophilic substitution of pyridine 135
7.11 Electrophilic substitution of pyrrole, furan and thiophene 136
8 Carbonyl compounds: aldehydes and ketones 139
8.1 Structure 139
8.2 Reactivity 140
8.3 Nucleophilic addition reactions 142
8.4 a-Substitution reactions 156
8.5 Carbonyl-carbonyl condensation reactions 160
9 Carbonyl compounds: carboxylic acids and derivatives 167
9.1 Structure 167
9.2 Reactivity 168
9.3 Nucleophilic acyl substitution reactions 168
9.4 Nucleophilic substitution reactions of carboxylic acids 170
9.5 Nucleophilic substitution reactions of acid chlorides 171
9.6 Nucleophilic substitution reactions of acid anhydrides 172
9.7 Nucleophilic substitution reactions of esters 173
9.8 Nucleophilic substitution and reduction reactions of amides 175
9.9 Nucleophilic addition reactions of nitriles 176
9.10 a-Substitution reactions of carboxylic acids 178
9.11 Carbonyl-carbonyl condensation reactions 178
10 Spectroscopy 185
10.1 Mass spectrometry (MS) 185
10.2 The electromagnetic spectrum 189
10.3 Ultraviolet (UV) spectroscopy 190
10.4 Infrared (IR) spectroscopy 192
10.5 Nuclear magnetic resonance (NMR) spectroscopy 194
11 Natural products and synthetic polymers 207
11.1 Carbohydrates 207
11.2 Lipids 209
11.3 Amino acids, peptides and proteins 211
11.4 Nucleic acids 213
11.5 Synthetic polymers 214
Worked example 218
Problems 219
Appendix 1: Bond dissociation enthalpies 221
Appendix 2: Bond lengths 223
Appendix 3: Approximate pKa values (relative to water) 225
Appendix 4: Useful abbreviations 227
Appendix 5: Infrared absorptions 229
Appendix 6: Approximate NMR chemical shifts 231
Appendix 7: Reaction summaries 235
Appendix 8: Glossary 241
Further reading 249
Outline answers 251
Index 277
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“I recommend instructors delivering undergraduate organic chemistry consider promoting this textbook to their students as a keynote revision guide.” (Appl. Organometal. Chem, 17 November 2014)
