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Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry annotated edition [Kõva köide]

  • Formaat: Hardback, 710 pages, kõrgus x laius x paksus: 254x199x45 mm, kaal: 1496 g, illustrations
  • Ilmumisaeg: 13-Apr-2006
  • Kirjastus: John Wiley & Sons Inc
  • ISBN-10: 0470016655
  • ISBN-13: 9780470016657
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  • Formaat: Hardback, 710 pages, kõrgus x laius x paksus: 254x199x45 mm, kaal: 1496 g, illustrations
  • Ilmumisaeg: 13-Apr-2006
  • Kirjastus: John Wiley & Sons Inc
  • ISBN-10: 0470016655
  • ISBN-13: 9780470016657
Teised raamatud teemal:
Essentials of Organic Chemistry is an accessible introduction to the subject for students of Pharmacy, Medicinal Chemistry and Biological Chemistry. Designed to provide a thorough grounding in fundamental chemical principles, the book focuses on key elements of organic chemistry and carefully chosen material is illustrated with the extensive use of pharmaceutical and biochemical examples.

In order to establish links and similarities the book places prominence on principles and deductive reasoning with cross-referencing. This informal text also places the main emphasis on understanding and predicting reactivity rather than synthetic methodology as well as utilising a mechanism based layout and featuring annotated schemes to reduce the need for textual explanations.
* tailored specifically to the needs of students of Pharmacy Medical Chemistry and Biological Chemistry
* numerous pharmaceutical and biochemical examples
* mechanism based layout
* focus on principles and deductive reasoning

This will be an invaluable reference for students of Pharmacy Medicinal and Biological Chemistry.


"...I look forward to using Dewick's book in coming years to add even more 'life' to the subject of organic chemistry." (Journal of Chemical Education, February 2008)

1. Molecular representations and nomenclature.
1.1 Molecular representations.
1.2 Partial structures.
1.3 Functional groups.
1.4 Systematic nomenclature.
1.5 Common groups and abbreviations.
1.6 Common, non-systematic names.
1.7 Trivial names for complex structures.
1.8 Acronyms.
1.9 Pronunciation.
2. Atomic structure and bonding.
2.1 Atomic structure.
2.2 Bonding and valency.
2.3 Atomic orbitals.
2.4 Electronic configurations.
2.5 Ionic bonding.
2.6 Covalent bonding.
2.6.1 Molecular orbitals: σ and π bonds.
2.6.2 Hybrid orbitals in carbon.
2.6.3 Hybrid orbitals in oxygen and nitrogen.
2.7 Bond polarity.
2.8 Conjugation.
2.9 Aromaticity.
2.9.1 Benzene.
2.9.2 Cyclooctatetraene.
2.9.3 H¨uckel’s rule.
2.9.4 Kekul´e structures.
2.9.5 Aromaticity and ring currents.
2.9.6 Aromatic heterocycles.
2.9.7 Fused rings.
2.10 Resonance structures and curly arrows.
2.11 Hydrogen bonding.
2.12 Molecular models.
3. Stereochemistry.
3.1 Hybridization and bond angles.
3.2 Stereoisomers.
3.3 Conformational isomers.
3.3.1 Conformations of acyclic compounds.
3.3.2 Conformations of cyclic compounds.
3.4 Configurational isomers.
3.4.1 Optical isomers: chirality and optical activity.
3.4.2 Cahn–Ingold–Prelog system to describe configuration  at chiral centres.
3.4.3 Geometric isomers.
3.4.4 Configurational isomers with several chiral centres.
3.4.5 Meso compounds.
3.4.6 Chirality without chiral centres.
3.4.7 Prochirality.
3.4.8 Separation of enantiomers: resolution.
3.4.9 Fischer projections.
3.4.10 D and L configurations.
3.5 Polycyclic systems.
3.5.1 Spiro systems.
3.5.2 Fused ring systems.
3.5.3 Bridged ring systems.
4. Acids and bases.
4.1 Acid–base equilibria.
4.2 Acidity and pKa values.
4.3 Electronic and structural features that influence acidity.
4.3.1 Electronegativity.
4.3.2 Bond energies.
4.3.3 Inductive effects.
4.3.4 Hybridization effects.
4.3.5 Resonance/delocalization effects.
4.4 Basicity.
4.5 Electronic and structural features that influence basicity.
4.5.1 Electronegativity.
4.5.2 Inductive effects.
4.5.3 Hybridization effects.
4.5.4 Resonance/delocalization effects.
4.6 Basicity of nitrogen heterocycles.
4.7 Polyfunctional acids and bases.
4.8 pH.
4.9 The Henderson–Hasselbalch equation.
4.10 Buffers.
4.11 Using pKa values.
4.11.1 Predicting acid–base interactions.
4.11.2 Isotopic labelling using basic reagents.
4.11.3 Amphoteric compounds: amino acids.
4.11.4 pKa and drug absorption.
5. Reaction mechanisms.
5.1 Ionic reactions.
5.1.1 Bond polarity.
5.1.2 Nucleophiles, electrophiles, and leaving groups.
5.2 Radical reactions.
5.3 Reaction kinetics and mechanism.
5.4 Intermediates and transition states.
5.5 Types of reaction.
5.6 Arrows.
6. Nucleophilic reactions: nucleophilic substitution.
6.1 The SN2 reaction: bimolecular nucleophilic substitution.
6.1.1 The effect of substituents.
6.1.2 Nucleophiles: nucleophilicity and basicity.
6.1.3 Solvent effects.
6.1.4 Leaving groups.
6.1.5 SN2 reactions in cyclic systems.
6.2 The SN1 reaction: unimolecular nucleophilic substitution.
6.2.1 The effect of substituents.
6.2.2 SN1 reactions in cyclic systems.
6.2.3 SN1 or SN2?
6.3 Nucleophilic substitution reactions.
6.3.1 Halide as a nucleophile: alkyl halides.
6.3.2 Oxygen and sulfur as nucleophiles: ethers, esters, thioethers, epoxides.
6.3.3 Nitrogen as a nucleophile: ammonium salts, amines.
6.3.4 Carbon as a nucleophile: nitriles, Grignard reagents, acetylides.
6.3.5 Hydride as nucleophile: lithium aluminium hydride and sodium borohydride reductions.
6.3.6 Formation of cyclic compounds.
6.4 Competing reactions: eliminations and rearrangements.
6.4.1 Elimination reactions.
6.4.2 Carbocation rearrangement reactions.
7. Nucleophilic reactions of carbonyl groups.
7.1 Nucleophilic addition to carbonyl groups: aldehydes and ketones.
7.1.1 Aldehydes are more reactive than ketones.
7.1.2 Nucleophiles and leaving groups: reversible addition reactions.
7.2 Oxygen as a nucleophile: hemiacetals, hemiketals, acetals and ketals.
7.3 Water as a nucleophile: hydrates.
7.4 Sulfur as a nucleophile: hemithioacetals, hemithioketals, thioacetals and thioketals.
7.5 Hydride as a nucleophile: reduction of aldehydes and ketones, lithium aluminium hydride and sodium borohydride.
7.6 Carbon as a nucleophile.
7.6.1 Cyanide: cyanohydrins.
7.6.2 Organometallics: Grignard reagents and acetylides.
7.7 Nitrogen as a nucleophile: imines and enamines.
7.7.1 Imines.
7.7.2 Enamines.
7.8 Nucleophilic substitution on carbonyl groups: carboxylic acid derivatives.
7.9 Oxygen and sulfur as nucleophiles: esters and carboxylic acids.
7.9.1 Alcohols: ester formation.
7.9.2 Water: hydrolysis of carboxylic acid derivatives.
7.9.3 Thiols: thioacids and thioesters.
7.10 Nitrogen as a nucleophile: amides.
7.11 Hydride as a nucleophile: reduction of carboxylic acid derivatives.
7.12 Carbon as a nucleophile: Grignard reagents.
7.13 Nucleophilic substitution on derivatives of sulfuric and phosphoric acids.
7.13.1 Sulfuric acid derivatives.
7.13.2 Phosphoric acid derivatives.
8. Electrophilic reactions.
8.1 Electrophilic addition to unsaturated carbon.
8.1.1 Addition of hydrogen halides to alkenes.
8.1.2 Addition of halogens to alkenes.
8.1.3 Electrophilic additions to alkynes.
8.1.4 Carbocation rearrangements.
8.2 Electrophilic addition to conjugated systems.
8.3 Carbocations as electrophiles.
8.4 Electrophilic aromatic substitution.
8.4.1 Electrophilic alkylations: Friedel–Crafts reactions.
8.4.2 Electrophilic acylations: Friedel–Crafts reactions.
8.4.3 Effect of substituents on electrophilic aromatic substitution.
8.4.4 Electrophilic substitution on polycyclic aromatic compounds.
9. Radical reactions.
9.1 Formation of radicals.
9.2 Structure and stability of radicals.
9.3 Radical substitution reactions: halogenation.
9.3.1 Stereochemistry of radical reactions.
9.3.2 Allylic and benzylic substitution: halogenation reactions.
9.4 Radical addition reactions: addition of HBr to alkenes.
9.4.1 Radical addition of HBr to conjugated dienes.
9.4.2 Radical polymerization of alkenes.
9.4.3 Addition of hydrogen to alkenes and alkynes: catalytic hydrogenation.
9.5 Radical addition of oxygen: autoxidation reactions.
9.6 Phenolic oxidative coupling.
10. Nucleophilic reactions involving enolate anions.
10.1 Enols and enolization.
10.1.1 Hydrogen exchange.
10.1.2 Racemization.
10.1.3 Conjugation.
10.1.4 Halogenation.
10.2 Alkylation of enolate anions.
10.3 Addition–dehydration: the aldol reaction.
10.4 Other stabilized anions as nucleophiles: nitriles and nitromethane.
10.5 Enamines as nucleophiles.
10.6 The Mannich reaction.
10.7 Enolate anions from carboxylic acid derivatives.
10.8 Acylation of enolate anions: the Claisen reaction.
10.8.1 Reverse Claisen reactions.
10.9 Decarboxylation reactions.
10.10 Nucleophilic addition to conjugated systems: conjugate addition  and Michael reactions.
11. Heterocycles.
11.1 Heterocycles.
11.2 Non-aromatic heterocycles.
11.3 Aromaticity and heteroaromaticity.
11.4 Six-membered aromatic heterocycles.
11.4.1 Pyridine.
11.4.2 Nucleophilic addition to pyridinium salts.
11.4.3 Tautomerism: pyridones.
11.4.4 Pyrylium cation and pyrones.
11.5 Five-membered aromatic heterocycles.
11.5.1 Pyrrole.
11.5.2 Furan and thiophene.
11.6 Six-membered rings with two heteroatoms.
11.6.1 Diazines.
11.6.2 Tautomerism in hydroxy- and amino-diazines.
11.7 Five-membered rings with two heteroatoms.
11.7.1 1,3-Azoles: imidazole, oxazole, and thiazole.
11.7.2 Tautomerism in imidazoles.
11.7.3 Reactivity of 1,3-azoles.
11.7.4 1,2-Azoles: pyrazole, isoxazole, and isothiazole.
11.8 Heterocycles fused to a benzene ring.
11.8.1 Quinoline and isoquinoline.
11.8.2 Indole.
11.9 Fused heterocycles.
11.9.1 Purines.
11.9.2 Pteridines.
11.10 Some classic aromatic heterocycle syntheses.
11.10.1 Hantzsch pyridine synthesis.
11.10.2 Skraup quinoline synthesis.
11.10.3 Bischler–Napieralski isoquinoline synthesis.
11.10.4 Pictet–Spengler tetrahydroisoquinoline synthesis.
11.10.5 Knorr pyrrole synthesis.
11.10.6 Paal–Knorr pyrrole synthesis.
11.10.7 Fischer indole synthesis.
12. Carbohydrates.
12.1 Carbohydrates.
12.2 Monosaccharides.
12.2.1 Enolization and isomerization.
12.2.2 Cyclic hemiacetals and hemiketals.
12.2.3 The anomeric centre.
12.3 Alditols.
12.4 Glycosides.
12.5 Cyclic acetals and ketals: protecting groups.
12.6 Oligosaccharides.
12.7 Polysaccharides.
12.7.1 Structural aspects.
12.7.2 Hydrolysis of polysaccharides.
12.8 Oxidation of sugars: uronic acids.
12.9 Aminosugars.
12.10 Polymers containing aminosugars.
13. Amino acids, peptides and proteins.
13.1 Amino acids.
13.2 Peptides and proteins.
13.3 Molecular shape of proteins: primary, secondary and tertiary structures.
13.3.1 Tertiary structure: intramolecular interactions.
13.3.2 Protein binding sites.
13.4 The chemistry of enzyme action.
13.4.1 Acid–base catalysis.
13.4.2 Enolization and enolate anion biochemistry.
13.4.3 Thioesters as intermediates.
13.4.4 Enzyme inhibitors.
13.5 Peptide biosynthesis.
13.5.1 Ribosomal peptide biosynthesis.
13.5.2 Non-ribosomal peptide biosynthesis.
13.6 Peptide synthesis.
13.6.1 Protecting groups.
13.6.2 The dicyclohexylcarbodiimide coupling reaction.
13.6.3 Peptide synthesis on polymeric supports.
13.7 Determination of peptide sequence.
14. Nucleosides, nucleotides and nucleic acids.
14.1 Nucleosides and nucleotides.
14.2 Nucleic acids.
14.2.1 DNA.
14.2.2 Replication of DNA.
14.2.3 RNA.
14.2.4 The genetic code.
14.2.5 Messenger RNA synthesis: transcription.
14.2.6 Transfer RNA and translation.
14.3 Some other important nucleosides and nucleotides: ATP, SAM,  Coenzyme A, NAD, FAD.
14.4 Nucleotide biosynthesis.
14.5 Determination of nucleotide sequence.
14.5.1 Restriction endonucleases.
14.5.2 Chemical sequencing.
14.6 Oligonucleotide synthesis: the phosphoramidite method.
14.7 Copying DNA: the polymerase chain reaction.
15. The organic chemistry of intermediary metabolism.
15.1 Intermediary metabolism.
15.1.1 Oxidation reactions and ATP.
15.1.2 Oxidative phosphorylation and the electron transport chain.
15.2 The glycolytic pathway.
15.3 The Krebs cycle.
15.4 Oxidation of fatty acids.
15.4.1 Metabolism of saturated fatty acids.
15.4.2 Metabolism of unsaturated fatty acids.
15.5 Synthesis of fatty acids.
15.6 Amino acids and transamination.
15.7 PLP-dependent reactions.
15.8 TPP-dependent reactions.
15.9 Biotin-dependent carboxylations.
16. How to approach examination questions: selected problems and answers.
16.1 Examination questions: useful advice.
16.2 How to approach the problem: ‘Propose a mechanism for . . .’
16.3 Worked problems.

Dr Paul Dewick, School of Pharmacy, University of Nottingham, Nottigham NG7 2RD Paul Dewick is the author of the successful Medicinal Natural Product, 2/E and is a well-respected academic within his field.

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