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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.
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Keynotes in organic chemistry / / Andrew F. Parsons
