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Organic Chemistry

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Praise for the first edition: "Summing Up: Recommended"CHOICE, June 2011 "After a brief historical overview and a chapter on the a... Lire la suite
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Description

Praise for the first edition:

"Summing Up: Recommended"
CHOICE, June 2011

"After a brief historical overview and a chapter on the acid-base theme, the standard programme is rolled out, although with an almost unbroken emphasis on the acid-base approach
the body of the text is easy to read, and the well chosen questions following almost every paragraph encourage the reader to start digesting the provided information immediately."
Martina Lahmann in Education in Chemistry, May 2011

"This new book is designed to provide a new approach to teaching organic chemistry, to understand the relationships between functional group via an acid-base theme. In 28 chapters the author provides a mechanistic approach to teaching organic chemistry, focusing on fundamental principles rather than a comprehensive accumulation of factual knowledge."
Organic Process Research, 2011



Auteur

Michael B. Smith, University of Connecticut, Storrs, USA



Résumé

Based on the premise that many, if not most, reactions in organic chemistry can be explained by variations of fundamental acidbase concepts, Organic Chemistry: An AcidBase Approach provides a framework for understanding the subject that goes beyond mere memorization. Using several techniques to develop a relational understanding, it helps students fully grasp the essential concepts at the root of organic chemistry.

This new edition was rewritten largely with the feedback of students in mind and is also based on the author's classroom experiences using the first edition.

Highlights of the Second Edition Include:

  • Reorganized chapters that improve the presentation of material
  • Coverage of new topics, such as green chemistry
  • Adding photographs to the lectures to illustrate and emphasize important concepts
  • A downloadable solutions manual

The second edition of Organic Chemistry: An AcidBase Approach constitutes a significant improvement upon a unique introductory technique to organic chemistry. The reactions and mechanisms it covers are the most fundamental concepts in organic chemistry that are applied to industry, biological chemistry, biochemistry, molecular biology, and pharmacy. Using an illustrated conceptual approach rather than presenting sets of principles and theories to memorize, it gives students a more concrete understanding of the material.



Contenu

Introduction
Brief History of Organic Chemistry
Variety and Beauty of Organic Molecules
Notes

Why Is an AcidBase Theme Important?
Acids and Bases in General Chemistry
Acids and Bases in Organic Chemistry
There Are Two AcidBase Definitions: How Are They Related?
Acid and Base Strength
Electronegativity and Atom Size
Determination of AcidBase Strength Based on Electronegativity and Size Arguments
Lewis Acids and Bases
Why Is AcidBase Chemistry a Theme for Organic Chemistry?
Biological Relevance
Correlation of Concepts with Homework
Answers to In-Chapter Questions
Homework
Notes

Bonding
Orbitals and the Periodic Table
Ionic versus Covalent Chemical Bonds
Covalent Bonds
Strength of a Covalent Bond
Molecular Orbitals
Tetrahedral Carbons and sp3 Hybridization
Breaking Covalent Bonds
Polarized Covalent -Bonds
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Alkanes, Isomers, and an Introduction to Nomenclature
Fundamental Structure of Alkanes Based on the sp3-Hybrid Model
Millions of Alkane Hydrocarbons
Acid or Base Properties of Alkanes
Naming Millions of Isomers: Rules of Nomenclature: The IUPAC Rules of Nomenclature
Rings Made of Carbon: Cyclic Compounds
Combustion Analysis and Empirical Formulas
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Functional Groups
Introducing a Functional Group: Alkenes
AcidBase Properties of Alkenes
Hydrocarbon Functional Groups: Alkynes
Hydrocarbons with Several -Bonds
Heteroatoms and Polarized Covalent -Bonds
Formal Charge
Reactive Intermediates
Heteroatom Functional Groups
AcidBase Properties of Functional Groups
Physical Properties and Intermolecular Forces
Functional Groups with Polarized -Bonds
Benzene: A Special Cyclic Hydrocarbon
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Acids, Bases, Nucleophiles, and Electrophiles
AcidBase Equilibria
Factors That Influence Ka
Factors That Influence the Strength of a Carboxylic Acid
Energetics and Reaction Curves
Alcohols and Amines Are Acids
Hydrogen Atom Attached to a Carbon Is an Acid
AcidBase Reaction of Alkenes with Mineral Acids
Lewis Acids and Bases
Organic Bases
Nucleophiles
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Chemical Reactions, Bond Energy, and Kinetics
Chemical Reaction
Free Energy: Influence of Enthalpy and Entropy
Bond-Dissociation Enthalpy and Reactions
Transition States
Energetics: Starting Materials, Transition States, Intermediaries, and Products on a Reaction Curve
Competing Reactions
Reaction Curves and Intermediaries
Mechanisms
Why Does a Chemical Reaction Occur? Defining a "Reactive" Center
Reversible Chemical Reactions
Kinetics
No Reaction
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Rotamers and Conformation
Rotamers
Longer Chain Alkanes
Conformations of Alkenes and Alkynes: Introducing -Bonds
Influence of Heteroatoms on the Rotamer Population
Cyclic Alkanes
Substituted Cyclohexanes
Larger Rings
Cyclic Alkenes
Introducing Heteroatoms into a Ring
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Stereoisomers: Chirality, Enantiomers, and Diastereomers
Stereogenic Carbons and Stereoisomers
Absolute Configuration [(R) and (S) Nomenclature]
Specific Rotation: A Physical Property
Relationship of Specific Rotation and Absolute Configuration
Mixtures of Enantiomers and Racemates
Alkenes
Diastereomers
Stereogenic Centers in Cyclic Molecules
Stereogenic Centers in Complex Molecules
Optical Resolution
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

AcidBase Reactions of -Bonds: Addition Reactions
Alkenes and AcidBase Chemistry
Carbocation Intermediates
Alkenes React with Weak Acids in the Presence of an Acid Catalyst
Alkenes React as Lewis Bases with Dihalogens
Alkenes React as Lewis Bases with Borane
Alkenes React as Lewis Bases with Mercury(II) Compounds
Alkynes React as BrønstedLowry Bases or Lewis Bases
Oxidation Reactions of Alkenes
Nonionic Reactions: Radicals and Alkene Polymerization
Synthetic Transformations
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Nucleophiles: Lewis Base-Like Reactions at sp3 Carbon
Alkyl Halides, Sulfonate Esters, and the Electrophilic C-X Bond
Nucleophiles and Bimolecular Substitution (the SN2 Reaction)
Functional Group Transformations via the SN2 Reaction
Tertiary Halide Reacts with a Nucleophile When the Solvent Is Water
Solvolysis Reactions of Alkyl Halides
Preparation of Halides by Substitution Reactions
Reactions of Ethers
Free Radical Halogenation of Alkanes
Synthetic Transformations
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Bases-Induced Elimination Reactions
Bimolecular Elimination
Stereochemical Consequences of the E2 Reaction
E2 Reaction in Cyclic Molecules
Unimolecular Elimination: The E1 Reaction
Intramolecular Elimination
1,3-Elimination: Decarboxylation
Elimination Reactions of Vinyl Halides: Formation of Alkynes
Functional Group Exchanges Based on Elimination
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Substitution and Elimination Reactions Can Compete
Few Simplifying Assumptions
Protic versus Aprotic and Water
Nucleophilic Strength versus Base Strength
Nature of the Halide
What about Secondary Halides?
Strength and Limitations of the Simplifying Assumptions
When Do the Assumptions Fail?
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Spectroscopic Methods of Identification
Light and Energy
Mass Spectrometry
Infrared Spectroscopy
Nuclear Magnetic Resonance Spectroscopy
Identifying Monofunctional Molecules
Carbon-13 NMR Spectroscopy: Counting the Carbons
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Organic Molecules That Contain Alkali Metals or Transition Metals (Organometallics)
Introducing Magnesium into a Molecule
Reaction of Aryl and Vinyl Halides with Magnesium
Grignard Reagents Are Bases
Grignard Reagents Are Poor Nucleophiles with Alkyl Halides
Organolithium Reagents
Organocuprates
Organometallic Disconnections
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Carbonyl Compounds: Structure, Nomenclature, Reactivity
Carbonyl Group
Aldehydes and Ketones: Nomenclature
Chemical Reactivity of Ketones and Aldehydes
Carboxylic Acids: Nomenclature and Properties
Dicarboxylic Acids
Dicarboxylic Acids Have Two pKa Values
Carboxylic Acid Derivatives: Structure and Nomenclature
Acyl Substitution with Carboxylic Acid Derivatives
Sulfonic Acids
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Oxidation
Defining and Oxidation
Oxidation of Alcohols with Chromium (VI)
Oxidation of Alkenes Revisited
Oxidative Cleavage
Summary of Functional Group Exchanges
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Reactions of Aldehydes and Ketones
Chemical Reactivity of the Carbonyl Group
Reaction of Aldehydes or Ketones with Strong Nucleophiles
Weak Nucleophiles: Reversible versus Irreversible Acyl Addition
Alcohols: Weak Nucleophiles That Yield Reactive Products
Amines Are Nucleophiles
CarbonCarbon Bond-Forming Reactions and Functional Group Modification
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Reduction
Defining a Reduction
Hydrides as Reducing Agents
Hydride Reduction of Other Functional Groups
Catalytic Hydrogenation
Dissolving Metal Reductions
Summary of Functional Group Exchanges
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Carboxylic Acid Derivatives and Acyl Substitution
Chemical Reactivity of Carboxylic Acid Derivatives
Acyl Substitution: Hydrolysis of Acid Derivatives
Preparation of Acid Chlorides
Preparation of Acid Anhydrides
Preparation of Esters
Preparation of Amides
Reaction of Carboxylic Acid Derivatives with Carbon Nucleophiles
Reaction of Organometallics with Electrophilic "Carbonyl" Molecules
Dicarboxylic Acid Derivatives
BaeyerVilliger Oxidation
Sulfonic Acids and Derivatives
Nitrate Esters, Sulfate Esters, and Phosphate Esters
Nitriles Are Carboxylic Acid Derivatives
CarbonCarbon Bond-Forming Reactions and Functional Group Exchanges of Acid Derivatives
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Aromatic Compounds and Benzene Derivatives
Benzene and Aromaticity
Functionalized Benzene Derivatives and a New Nomenclature System
Electrophilic Aromatic Substitution
Disubstituted Benzene Derivatives
Polysubstituted Benzene Derivatives
Reduction of Aromatic Compounds
Aromaticity in Monocyclic Molecules Other than Benzene
Polynuclear Aromatic Hydrocarbons
Nucleophilic Aromatic Substitution
Aromatic Amines and Diazonium Salts
Benzyne Intermediates
Aromatic Disconnections and Functional Group Exchange Reactions
Synthesis of Aromatic Compounds
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Enolate Anions: Acyl Addition and Acyl Substitution
Aldehydes and Ketones Are Weak Acids
Nonnucleophilic Bases
Enolate Alkylation
Acyl Addition Reactions
Enolate Anions from Unsymmetrical Ketones
Intramolecular Aldol Condensation
Ester Enolate Anions
Decarboxylation
Knoevenagel Reaction, the Malonic Ester Synthesis, and the Acetoacetic Acid Synthesis
Phosphorus Ylids and the Wittig Reaction
New Synthetic Possibilities
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Difunctional Molecules: Dienes and Conjugated Carbonyl Compounds
Conjugated Dienes
Conjugated Carbonyl Compounds
Detecting Conjugation with Spectroscopy
Reactions of Conjugated -Bonds
Michael Addition
Hydroperoxide Anions and Conjugated Carbonyls
Synthetic Possibilities
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Difunctional Molecules: Pericyclic Reactions
The DielsAlder Reaction
Reactivity of Dienes and Alkenes
Selectivity in the DielsAlder Reaction
Sigmatropic Rearrangements
Review of Synthetic Transformations
Organization of Reaction Types
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Retrosynthesis and Synthesis
What Is Synthesis?
Synthesis Based on a Specified Starting Material for a Given Target
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Heteroaromatic Compounds
Nitrogen in an Aromatic Ring
Oxygen and Sulfur in an Aromatic Ring
Substitution Reactions in Monocyclic Heterocyclic Aromatic Compounds
Reduced Forms of Heterocycles
Heteroaromatic Compounds with More Than One Ring
Aromatic Substitution Reactions of Polycyclic Heterocycles
Biological Relevance
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Multifunctional Compounds: Amino Acids and Peptides
Review of Reactions That Form Amines
Reactions of Amines
Difunctional Molecules: Amino Acids
Synthesis of -Amino Acids
Biological Relevance: Peptides Are Poly(amides) of Amino Acid Residues
Biological Relevance: Proteins and Enzymes Are Poly(peptides)
Determination of the Primary Structure of a Peptide
New Synthetic Methodology
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Multifunctional Compounds: Carbohydrates
Polyhydroxy Carbonyl Compounds
Disaccharides, Trisaccharides, Oligosaccharides, and Polysaccharides
Reactions of Carbohydrates
Biological Relevance: Nucleosides and Nucleotides
Biological Relevance: Polynucleotides
Correlation of Homework with Concepts
Answers to In-Chapter Questions
Homework
Notes

Informations sur le produit

Titre: Organic Chemistry
Auteur:
Code EAN: 9781138624474
ISBN: 978-1-138-62447-4
Format: Couverture cartonnée
Editeur: Taylor and Francis
Genre: Chimie
nombre de pages: 1128
Poids: g
Taille: H279mm x B216mm
Année: 2018
Auflage: 2. A.

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