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March's Advanced Organic Chemistry : Reactions, Mechanisms, and Structure

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9780470462591

ISBN10:
0470462590
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Pub. Date:
4/8/2013
Publisher(s):
Wiley
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    March's Advanced Organic Chemistry : Reactions, Mechanisms, and Structure




Summary

The definitive resource for students and professionals in organic chemistry, the Seventh Edition of Marchs Advanced Organic Chemistry continues to prove to be a must-have resource for planning and execution of synthetic reactions. Each chapter has been updated to reflect the most recent reaction information with references to both the primary and review literature. Heavily revised throughout, this seventh edition clearly explains the theories and examples of organic chemistry and guides readers on planning and execution of multi-step synthetic reactions, with detailed descriptions of all the reactions.

Author Biography

MICHAEL B. SMITH, PhD, is Professor in the Department of Chemistry at the University of Connecticut. He is a coauthor of the fifth and sixth editions of March's Advanced Organic Chemistry and the author of Volumes 6 –12 of the Compendium of Organic Synthetic Methods (Wiley) as well as several other monographs.

Table of Contents

PREFACE

BIOGRAPHICAL STATEMENT

PART   1

CHAPTER 1     LOCALIZED CHEMICAL BONDING

1.A. COVALENT BONDING

1.B.  MULTIPLE VALENCE

1.C.  HYBRIDIZATION

1.D.  MULTIPLE BONDS

1.E.  PHOTOELECTRON SPECTROSCOPY

1.F.  ELECTRONIC STRUCTURES OF MOLECULES

1.G.  ELECTRONEGATIVITY

1.H. DIPOLE MOMENT

1.I.  INDUCTIVE AND FIELD EFFECTS

1.J.  BOND DISTANCES

1K.  BOND ANGLES

1.L.  BOND ENERGIES

CHAPTER TWO     DELOCALIZED CHEMICAL BONDING

2.A.   MOLECULAR ORBITALS

2.B.   BOND ENERGIES AND DISTANCES IN COMPOUNDS CONTAINING DELOCALIZED BONDS

2.C.   MOLECULES THAT HAVE DELOCALIZED BONDS

2.D.   CROSS CONJUGATION

2.E.   THE RULES OF RESONANCE

2.F.   THE RESONANCE EFFECT

2.G.   STERIC INHIBITION OF RESONANCE AND THE INFLUENCES OF STRAIN

2.H.   pπ-dπ BONDING.  YLIDS

2.I.   AROMATICITY

2.I.i.   Six-Membered Rings

2.I.ii.   Five, Seven, and Eight-Membered Rings

2.I.iii.   Other Systems Containing Aromatic Sextets

2.J.   ALTERNANT AND NONALTERNANT HYDROCARBONS

2.K.  AROMATIC SYSTEMS WITH ELECTRON NUMBERS OTHER THAN SIX

2.K.i.  Systems of Two Electrons

2.K.ii.  Systems of Four Electrons:  Antiaromaticity

2.K.iii.  Systems of Eight Electrons

2.K.iv.  Systems of Ten Electrons

2.K.v.  Systems of More than Ten Electrons: 4n + 2 Electrons

2.K.vi.  Systems of More Than Ten Electrons: 4n Electrons

2.L.  OTHER AROMATIC COMPOUNDS

2.M.  HYPERCONJUGATION

2.N.  TAUTOMERISM

2.N.i.  Keto-Enol Tautomerism

2.N.ii.  Other Proton-Shift Tautomerism

2.N.iii.  Valence Tautomerism

3     BONDING WEAKER THAN COVALENT

3.A. HYDROGEN BONDING

3.B. ?-? INTERACTIONS

3.C. ADDITION COMPOUNDS

3.C.i.   Electron Donor-Acceptor (EDA) Complexes

3.C.ii.  Crown Ether Complexes and Cryptates

3.C.iii.  Inclusion Compounds

3.C.iv.  Cyclodextrins

3.D. Catenanes and Rotaxanes

3.E.  Cucurbit[n]uril-Based Gyroscane

4     STEREOCHEMISTRY AND CONFORMATION

4.A. OPTICAL ACTIVITY AND CHIRALITY

4.B. Dependence of Rotation on Conditions of Measurement

4.C. What Kinds of Molecules Display Optical Activity?

4.D.  THE FISCHER PROJECTION

4.E.  ABSOLUTE CONFIGURATION

4.E.i.  THE CAHN-INGOLD-PRELOG SYSTEM

4.E.ii.  METHODS OF DETERMINING CONFIGURATION

4.F.  THE CAUSE OF OPTICAL ACTIVITY

4.G.  MOLECULES WITH MORE THAN ONE STEREOGENIC CENTER

4.H.  ASYMMETRIC SYNTHESIS

4.I.  METHODS OF RESOLUTION

4.J.  OPTICAL PURITY

4.K.  CIS-TRANS ISOMERISM

4.K.i.      Cis-Trans Isomerism Resulting from Double Bonds

4.K.ii.  Cis-Trans Isomerism of Monocyclic Compounds

4.K.iii.  Cis-Trans Isomerism of Fused and Bridged Ring Systems

4.L.  OUT-IN ISOMERISM

4.M.  ENANTIOTOPIC AND DIASTEREOTOPIC ATOMS, GROUPS, AND FACES

4.N.  STEREOSPECIFIC AND STEREOSELECTIVE SYNTHESES

4.O.  CONFORMATIONAL ANALYSIS

4.O.i.  Conformation in Open-Chain Systems

4.O.ii.  Conformation in Six-Membered Rings

4.O.iii.  Conformation in Six-Membered Rings Containing Heteroatoms

4.O.iv.  Conformation in Other Rings

4.P.  MOLECULAR MECHANICS

4.Q.  STRAIN

4.Q.i.  Strain in Small Rings

4.Q.ii.  Strain in Other Rings

4.Q.iii.  Unsaturated Rings

4.Q.iv.  Strain Due to Unavoidable Crowding

5   CARBOCATIONS, CARBANIONS, FREE RADICALS, CARBENES, AND NITRENES

5.A. CARBOCATIONS

5.A.i. Nomenclature

5.A.ii.  Stability and Structure of Carbocations

5.A.iii.  THE GENERATION AND FATE OF CARBOCATIONS

5.B.  CARBANIONS

5.B.i.  Stability and Structure

5.B.ii.  THE STRUCTURE OF ORGANOMETALLIC COMPOUNDS

5.B.iii.  THE GENERATION AND FATE OF CARBANIONS

5.C.  FREE RADICALS

5.C.i.  Stability and Structure

5.C.ii.  THE GENERATION AND FATE OF FREE RADICALS

5.C.iii.  RADICAL IONS

5.D.  CARBENES

5.D.i.  Stability and Structure

5.D.ii.  THE GENERATION AND FATE OF CARBENES

5.E.  NITRENES

6     MECHANISMS AND METHODS OF DETERMINING THEM

6.A.  TYPES OF MECHANISM

6.B.  TYPES OF REACTION

6.C.  THERMODYNAMIC REQUIREMENTS FOR REACTION

6.D.  KINETIC REQUIREMENTS FOR REACTION

6.E.   THE BALDWIN RULES FOR RING CLOSURE

6.F.  KINETIC AND THERMODYNAMIC CONTROL

6.G.  THE HAMMOND POSTULATE

6.H.  MICROSCOPIC REVERSIBILITY

6.I.  MARCUS THEORY

6.J.  METHODS OF DETERMINING MECHANISMS

6.J.i.  Identification of Products

6.J.ii.  Determination of the Presence of an Intermediate

6.J.iii.  The Study of Catalysis

6.J.iv.  Isotopic Labeling

6.J.v.  Stereochemical Evidence

6.J.vi.  Kinetic Evidence

6.J.vii.  Isotope Effects

7     IRRADIATION PROCESSES IN ORGANIC CHEMISTRY

7.A.  PHOTOCHEMISTRY

7.A.i.  Excited States and the Ground State

7.A.ii.  Singlet and Triplet States:  "Forbidden" Transitions

7.A.iii.  Types of Excitation

7.A.iv.  Nomenclature and Properties of Excited States

7.A.v.  Photolytic Cleavage

7.A.vi.  The Fate of the Excited Molecule: Physical Processes

7.A.vii.  The Fate of the Excited Molecule: Chemical Processes

7.A.viii.  The Determination of Photochemical Mechanisms

7.B.  SONOCHEMISTRY

7.C.  MICROWAVE CHEMISTRY

8       ACIDS AND BASES

8.A. BR?NSTED THEORY

8.A.i.  Bronsted Acids

8.A.ii.  Bronsted Bases

8.B.  THE MECHANISM OF PROTON TRANSFER REACTIONS

8.C. MEASUREMENTS OF SOLVENT ACIDITY

8.D. ACID AND BASE CATALYSIS

8.E. LEWIS ACIDS AND BASES

8.E.i.  Hard And Soft Acids And Bases

8.F. THE EFFECTS OF STRUCTURE ON THE STRENGTHS OF ACIDS AND BASES

8.G. THE EFFECTS OF THE MEDIUM ON ACID AND BASE STRENGTH

9     EFFECTS OF STRUCTURE AND MEDIUM ON REACTIVITY

9.A.  RESONANCE AND FIELD EFFECTS

9.B.  STERIC EFFECTS

9.C.  QUANTITATIVE TREATMENTS OF THE EFFECT OF STRUCTURE ON REACTIVITY

9.D.  EFFECT OF MEDIUM ON REACTIVITY AND RATE

9.D.i.  HIGH PRESSURE

9.D.ii.  WATER AND OTHER NON-ORGANIC SOLVENTS

9.D.iii.  IONIC SOLVENTS

9.D.iv.  SOLVENTLESS REACTIONS

PART   2

9.E.  IUPAC NOMENCLATURE FOR TRANSFORMATIONS

9.E.i.  Substitutions 

9.E.ii.  Additions 

9.F.  IUPAC SYSTEM FOR SYMBOLIC REPRESENTATION OF MECHANISMS

9.G.  ORGANIC SYNTHESES REFERENCES

10     ALIPHATIC SUBSTITUTION, NUCLEOPHILIC AND ORGANOMETALLIC

10.A.  MECHANISMS

10.A.i.  The SN2 Mechanism

10.A.ii.  The SN1 Mechanism

10.A.iii.  Ion Pairs in the SN1 Mechanism

10.A.iv.  Mixed SN1 and SN2 Mechanisms

10.B.   SET Mechanisms

10.C.  The Neighboring-Group Mechanism

10.C.i.  Neighboring-Group Participation by π and ? Bonds:  Nonclassical Carbocations

10.D.  The SNi Mechanism

10.E.  Nucleophilic Substitution at an Allylic Carbon:  Allylic Rearrangements

10.F.   Nucleophilic Substitution at an Aliphatic Trigonal Carbon:  The Tetrahedral Mechanism

10.G.  REACTIVITY

10.G.i.  The Effect of Substrate Structure

10.G.ii.  The Effect of the Attacking Nucleophile

10.G.iii.  The Effect of the Leaving Group

10.G.iv.  The Effect of the Reaction Medium

10.G.v.  Phase-Transfer Catalysis

10.G.vi.  Influencing Reactivity by External Means

10.G.vii.  Ambident (Bidentant) Nucleophiles:  Regioselectivity

10.G.viii.  Ambident Substrates

10.H.  REACTIONS

10.H.i.  OXYGEN NUCLEOPHILES

10.H.ii.  SULFUR NUCLEOPHILES

10.H.iii.  NITROGEN NUCLEOPHILES

10.H.iv.  HALOGEN NUCLEOPHILES

10.H.v.  CARBON NUCLEOPHILES

11       AROMATIC SUBSTITUTION, ELECTROPHILIC

11.A.  MECHANISMS

11.A.i.  The Arenium Ion Mechanism

11.A.ii.  The SE1 Mechanism

11.B.  ORIENTATION AND REACTIVITY

11.B.i.  Orientation and Reactivity in Monosubstituted Benzene Rings

11.B.ii.  The Ortho/Para Ratio

11.B.iii.  Ipso Attack

11.B.iv.  Orientation in Benzene Rings With More Than One Substituent

11.B.v.  Orientation in Other Ring Systems

11.C.  Quantitative Treatments of Reactivity in the Substrate

11.D.  A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship

11.E.  The Effect of the Leaving Group

11.F.  REACTIONS

11.F.i.  Hydrogen as the Leaving Group in Simple Substitution Reactions

11.F.ii.  HYDROGEN AS THE LEAVING GROUP IN REARRANGEMENT REACTIONS

11.F.iii.   OTHER LEAVING GROUPS

12.   ALIPHATIC, ALKENYL, AND ALKYNYL SUBSTITUTION, ELECTROPHILIC AND ORGANOMETALLIC

12.A.  MECHANISMS

12.A.i.  Bimolecular Mechanisms.  SE2 and SEi

12.A.ii.  THE SE1 MECHANISM

12.A.iii.  Electrophilic Substitution Accompanied by Double-Bond Shifts

12.A.iv.  Other Mechanisms

12.B.  REACTIVITY

12.C.  REACTIONS

12.C.i.  Hydrogen as Leaving Group

12.C.ii.  METALS AS LEAVING GROUPS

12.C.iii.  HALOGEN AS LEAVING GROUP

12.C.iv.  CARBON LEAVING GROUPS

12.C.v.  ELECTROPHILIC SUBSTITUTION AT NITROGEN

13.   AROMATIC SUBSTITUTION, NUCLEOPHILIC AND ORGANOMETALLIC

13.A.  MECHANISMS

13.A.i.  The SNAr Mechanism

13.A.ii.  The SN1 Mechanism

13.A.iii.  The Benzyne Mechanism

13.A.iv.  The SRN1 Mechanism

13.A.v.  Other Mechanisms

13.B.  REACTIVITY

13.B.i.  The Effect of Substrate Structure

13.B.ii.  The Effect of the Leaving Group

13.B.iii.  The Effect of the Attacking Nucleophile

13.C.  REACTIONS

13.C.i.  ALL LEAVING GROUPS EXCEPT HYDROGEN AND N2+

13.C.ii.  HYDROGEN AS LEAVING GROUP

13.C.iii.  NITROGEN AS LEAVING GROUP

13.C.iv.  REARRANGEMENTS

14          SUBSTITUTION REACTIONS, RADICAL

14.A. MECHANISMS

14.A.i.  Radical Mechanisms in General

14.A.ii. Free-Radical Substitution Mechanisms

14.A.iii.  Mechanisms at an Aromatic Substrate

14.A.iv.  Neighboring-Group Assistance in Free-Radical Reactions

14.B.  REACTIVITY

14.B.i.  Reactivity for Aliphatic Substrates

14.B.ii.  Reactivity at a Bridgehead

14.B.iii.  Reactivity in Aromatic Substrates

14.B.iv.  Reactivity in the Attacking Radical

14.B.v.  The Effect of Solvent on Reactivity

14.C.  REACTIONS

14.C.i.  HYDROGEN AS LEAVING GROUP

14.C.ii.  N2 AS LEAVING GROUP

14.C.iii.  METALS AS LEAVING GROUPS

14.C.iv.  HALOGEN AS LEAVING GROUP

14.C.v.  SULFUR AS LEAVING GROUP

14.C.vi.  CARBON AS LEAVING GROUP

15     ADDITION TO CARBON-CARBON MULTIPLE BONDS

15.A.  MECHANISMS

15.A.i  Electrophilic Addition

15.A.ii.  Nucleophilic Addition

15.A.iii.  Free-Radical Addition

15.A.iv.  Cyclic Mechanisms

15.B.  ORIENTATION AND REACTIVITY

15.B.i.  Reactivity

15.B.ii.  Orientation

15.B.iii.  Stereochemical Orientation

15.B.iv.  Addition to Cyclopropane Rings

15.C.  REACTIONS

15.C.i.  Isomerization Of Double And Triple Bonds

15.C.ii.  Reactions In Which Hydrogen Adds To One Side

15.C.ii.  Reactions In Which Hydrogen Adds To Neither Side

15.C.iii.  Cycloaddition Reactions

C16     ADDITION TO CARBON-HETERO MULTIPLE BONDS

16.A.  MECHANISM AND REACTIVITY

16.A.i.  Nucleophilic Substitution at an Aliphatic Trigonal Carbon. The Tetrahedral Mechanism

16.B.  REACTIONS

16.B.i.  Reactions In Which Hydrogen Or A Metallic Ion Adds To The Heteroatom

16.B.ii.  Acyl Substitution Reactions

16.B.iii.  Reactions In Which Carbon Adds To The Heteroatom

16.B.iv.  Addition To Isocyanides

16.B.v.  Nucleophilic Substitution At A Sulfonyl Sulfur Atom

CHAPTER 17     ELIMINATIONS

17.A. MECHANISMS AND ORIENTATION

17.A.i.  The E2 Mechanism

17.A.ii.  The E1 Mechanism

17.A.iii.  The E1cB Mechanism

17.A.iv.  The E1-E2-E1cB Spectrum

17.A.v.  The E2C Mechanism

17.B.  Regiochemistry of the Double Bond

17.C.  Stereochemistry of the Double Bond

17.D.  REACTIVITY

17.D.i.  Effect of Substrate Structure

17.D.ii.  Effect of the Attacking Base

17.D.iii.  Effect of the Leaving Group

17.D.iv.  Effect of the Medium

17.E.  MECHANISMS AND ORIENTATION IN PYROLYTIC ELIMINATIONS

17.E.i.  Mechanisms

17.E.ii.  Orientation in Pyrolytic Eliminations

17.E.iii.  1,4 Conjugate Eliminations

17.F.  REACTIONS

17.F.i.  Reactions In Which C=C And C?C Bonds Are Formed

17.F.ii.  Fragmentations

17.F.iii.  Reactions In Which C?N Or C=N Bonds Are Formed

17.F.iv.  Reactions In Which C=O Bonds Are Formed

17.F.v.  Reactions In Which N=N Bonds Are Formed

17.F.vi.  Extrusion Reactions

CHAPTER 18     REARRANGEMENTS

18.A.  MECHANISMS

18.A.i.  Nucleophilic Rearrangements

18.A.ii.  The Actual Nature of the Migration

18.A.iii.  Migratory Aptitudes

18.A.iv.  Memory Effects

18.B.  Longer Nucleophilic Rearrangements

18.C.  Free-Radical Rearrangements

18.D.  Carbene Rearrangements

18.E.  Electrophilic Rearrangements

18.F.  REACTIONS

18.F.i.  1,2-Rearrangements

18.F.ii.  Non-1,2 Rearrangements

CHAPTER 19     OXIDATIONS AND REDUCTIONS

19.A.  MECHANISMS

19.B.  REACTIONS

19.B.i.  Oxidations

19.B.ii.  Reductions

APPENDIX A     THE LITERATURE OF ORGANIC CHEMISTRY

A. PRIMARY SOURCES

A.i. Journals

A.ii. Patents

B. SECONDARY SOURCES

B.i. Listings of Titles

B.ii. Abstracts

B.iii. Beilstein

B.iv.  Tables of Information

C. REVIEWS

C.i. Annual Reviews

C.ii. Awareness Services

C.iii. General Treatises

C.iv. Monographs and Treatises on Specific Areas

C.v. Textbooks

C.vi.  Other Books

D.  LITERATURE SEARCHING

D.i.  Literature Searching Using Printed Materials

D.ii.  Literature Searching Online

D.iii.  Sci-Finder - the CAS database

D.iv.  Science Citation Index

D.v.  How to Locate Journal Articles

D.vi.  REAXYS

APPENDIX B

CLASSIFICATION OF REACTIONS BY TYPE OF COMPOUNDS SYNTHESIZED

AUTHOR INDEX

INDEX



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