Keynotes in organic chemistry / / Andrew F. Parsons

• Autore: Parsons A. F
• Pubblicazione: Chichester, West Sussex : , : Wiley, , 2014
• Edizione: Second edition.
• Descrizione fisica: 1 online resource (302 pages) : illustrations
• Disciplina: 547
• Soggetto topico: Chemistry, Organic
• Nota di bibliografia: Includes bibliographical references and index.
• Nota di contenuto: Keynotes in Organic Chemistry -- Contents -- Preface -- 1 Structure and bonding -- 1.1 Ionic versus covalent bonds -- 1.2 The octet rule -- 1.3 Formal charge -- 1.4 Sigma (σ-) and pi (π-) bonds -- 1.5 Hybridisation -- 1.6 Inductive effects, hyperconjugation and mesomeric effects -- 1.6.1 Inductive effects -- 1.6.2 Hyperconjugation -- 1.6.3 Mesomeric effects -- 1.7 Acidity and basicity -- 1.7.1 Acids -- 1.7.2 Bases -- 1.7.3 Lewis acids and bases -- 1.7.4 Basicity and hybridisation -- 1.7.5 Acidity and aromaticity -- 1.7.6 Acid-base reactions -- Worked example -- Problems -- 2 Functional groups, nomenclature and drawing organic compounds -- 2.1 Functional groups -- 2.2 Alkyl and aryl groups -- 2.3 Alkyl substitution -- 2.4 Naming carbon chains -- 2.4.1 Special cases -- 2.5 Drawing organic structures -- Worked example -- Problems -- 3 Stereochemistry -- 3.1 Isomerism -- 3.2 Conformational isomers -- 3.2.1 Conformations of ethane (CH3CH3) -- 3.2.2 Conformations of butane (CH3CH2CH2CH3) -- 3.2.3 Conformations of cycloalkanes -- 3.2.4 Cyclohexane -- 3.3 Configurational isomers -- 3.3.1 Alkenes -- 3.3.2 Isomers with chiral centres -- Worked example -- Problems -- 4 Reactivity and mechanism -- 4.1 Reactive intermediates: ions versus radicals -- 4.2 Nucleophiles and electrophiles -- 4.2.1 Relative strength -- 4.3 Carbocations, carbanions and carbon radicals -- 4.3.1 Order of stability -- 4.4 Steric effects -- 4.5 Oxidation levels -- 4.6 General types of reaction -- 4.6.1 Polar reactions (involving ionic intermediates) -- 4.6.2 Radical reactions -- 4.6.3 Pericyclic reactions -- 4.7 Ions versus radicals -- 4.8 Reaction selectivity -- 4.9 Reaction thermodynamics and kinetics -- 4.9.1 Thermodynamics -- 4.9.2 Kinetics -- 4.9.3 Kinetic versus thermodynamic control -- 4.10 Orbital overlap and energy -- 4.11 Guidelines for drawing reaction mechanisms. ; Worked example -- Problems -- 5 Halogenoalkanes -- 5.1 Structure -- 5.2 Preparation -- 5.2.1 Halogenation of alkanes -- 5.2.2 Halogenation of alcohols -- 5.2.3 Halogenation of alkenes -- 5.3 Reactions -- 5.3.1 Nucleophilic substitution -- 5.3.2 Elimination -- 5.3.3 Substitution versus elimination -- Worked example -- Problems -- 6 Alkenes and alkynes -- 6.1 Structure -- 6.2 Alkenes -- 6.2.1 Preparation -- 6.2.2 Reactions -- 6.3 Alkynes -- 6.3.1 Preparation -- 6.3.2 Reactions -- Worked example -- Problems -- 7 Benzenes -- 7.1 Structure -- 7.2 Reactions -- 7.2.1 Halogenation -- 7.2.2 Nitration -- 7.2.3 Sulfonation -- 7.2.4 Alkylation: The Friedel-Crafts alkylation -- 7.2.5 Acylation: The Friedel-Crafts acylation -- 7.3 Reactivity of substituted benzenes -- 7.3.1 Reactivity of benzene rings: Activating and deactivating substituents -- 7.3.2 Orientation of reactions -- 7.4 Nucleophilic aromatic substitution (the SNAr mechanism) -- 7.5 The formation of benzyne -- 7.6 Transformation of side chains -- 7.7 Reduction of the benzene ring -- 7.8 The synthesis of substituted benzenes -- 7.9 Electrophilic substitution of naphthalene -- 7.10 Electrophilic substitution of pyridine -- 7.11 Electrophilic substitution of pyrrole, furan and thiophene -- Worked example -- Problems -- 8 Carbonyl compounds: aldehydes and ketones -- 8.1 Structure -- 8.2 Reactivity -- 8.3 Nucleophilic addition reactions -- 8.3.1 Relative reactivity of aldehydes and ketones -- 8.3.2 Types of nucleophiles -- 8.3.3 Nucleophilic addition of hydride: reduction -- 8.3.4 Nucleophilic addition of carbon nucleophiles: formation of C-C bonds -- 8.3.5 Nucleophilic addition of oxygen nucleophiles: formation of hydrates and acetals -- 8.3.6 Nucleophilic addition of sulfur nucleophiles: formation of thioacetals -- 8.3.7 Nucleophilic addition of amine nucleophiles: formation of imines and enamines. ; 8.4 α-Substitution reactions -- 8.4.1 Keto-enol tautomerism -- 8.4.2 Reactivity of enols -- 8.4.3 Acidity of α-hydrogen atoms: enolate ion formation -- 8.4.4 Reactivity of enolates -- 8.5 Carbonyl-carbonyl condensation reactions -- 8.5.1 Condensations of aldehydes and ketones: the aldol condensation reaction -- 8.5.2 Crossed or mixed aldol condensations -- 8.5.3 Intramolecular aldol reactions -- 8.5.4 The Michael reaction -- Worked example -- Problems -- 9 Carbonyl compounds: carboxylic acids and derivatives -- 9.1 Structure -- 9.2 Reactivity -- 9.3 Nucleophilic acyl substitution reactions -- 9.3.1 Relative reactivity of carboxylic acid derivatives -- 9.3.2 Reactivity of carboxylic acid derivatives versus carboxylic acids -- 9.3.3 Reactivity of carboxylic acid derivatives versus aldehydes/ketones -- 9.4 Nucleophilic substitution reactions of carboxylic acids -- 9.4.1 Preparation of acid chlorides -- 9.4.2 Preparation of esters (esterification) -- 9.5 Nucleophilic substitution reactions of acid chlorides -- 9.6 Nucleophilic substitution reactions of acid anhydrides -- 9.7 Nucleophilic substitution reactions of esters -- 9.8 Nucleophilic substitution and reduction reactions of amides -- 9.9 Nucleophilic addition reactions of nitriles -- 9.10 α-Substitution reactions of carboxylic acids -- 9.11 Carbonyl-carbonyl condensation reactions -- 9.11.1 The Claisen condensation reaction -- 9.11.2 Crossed or mixed Claisen condensations -- 9.11.3 Intramolecular Claisen condensations: the Dieckmann reaction -- 9.12 A summary of carbonyl reactivity -- Worked example -- Problems -- 10 Spectroscopy -- 10.1 Mass spectrometry (MS) -- 10.1.1 Introduction -- 10.1.2 Isotope patterns -- 10.1.3 Determination of molecular formula -- 10.1.4 Fragmentation patterns -- 10.1.5 Chemical ionisation (CI) -- 10.2 The electromagnetic spectrum -- 10.3 Ultraviolet (UV) spectroscopy. ; 10.4 Infrared (IR) spectroscopy -- 10.5 Nuclear magnetic resonance (NMR) spectroscopy -- 10.5.1 1H NMR spectroscopy -- 10.5.2 13C NMR spectroscopy -- Worked example -- Problems -- 11 Natural products and synthetic polymers -- 11.1 Carbohydrates -- 11.2 Lipids -- 11.2.1 Waxes, fats and oils -- 11.2.2 Steroids -- 11.3 Amino acids, peptides and proteins -- 11.4 Nucleic acids -- 11.5 Synthetic polymers -- 11.5.1 Addition polymers -- 11.5.2 Condensation polymers -- Worked example -- Problems -- Appendix 1: Bond dissociation enthalpies -- Appendix 2: Bond lengths -- Appendix 3: Approximate pKa values (relative to water) -- Appendix 4: Useful abbreviations -- Appendix 5: Infrared absorptions -- Appendix 6: Approximate NMR chemical shifts -- Appendix 7: Reaction summaries -- Appendix 8: Glossary -- Further reading -- Outline answers -- Index.
• Sommario/riassunto: 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.
• Titolo autorizzato: Keynotes in organic chemistry
• ISBN: 9781118676417; 1118676416
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Lingua di pubblicazione: Inglese
• Record Nr.: 9910971892403321
• Lo trovi qui: Univ. Federico II