The Art of Writing Reasonable Organic Reaction Mechanisms (eBook, PDF) - Grossman, Robert B.
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Intended for students of intermediate organic chemistry, this text shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is the case in most textbooks. Each chapter discusses common mechanistic pathways and suggests practical tips for drawing them. Worked problems are included in the discussion of each mechanism, and "common error alerts" are scattered throughout the text to warn readers about pitfalls and misconceptions…mehr

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Produktbeschreibung
Intended for students of intermediate organic chemistry, this text shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is the case in most textbooks. Each chapter discusses common mechanistic pathways and suggests practical tips for drawing them. Worked problems are included in the discussion of each mechanism, and "common error alerts" are scattered throughout the text to warn readers about pitfalls and misconceptions that bedevil students. Each chapter is capped by a large problem set.


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  • Produktdetails
  • Verlag: Springer-Verlag GmbH
  • Seitenzahl: 435
  • Erscheinungstermin: 23. November 2019
  • Englisch
  • ISBN-13: 9783030287337
  • Artikelnr.: 58427747
Autorenporträt
¿Robert B. Grossman earned his A.B. degree at Princeton University and his Ph.D. at MIT. He then moved from Cambridge, Massachusetts to Cambridge, England for his postdoctoral work. In 1994, he moved from the United Kingdom (UK) to the University of Kentucky (UK), where he has been ever since. At UK, Dr. Grossman maintains an active research program focused on synthetic methodology, target-directed synthesis, and biosynthesis. He is also the creator of ACE Organic, a Web-based organic chemistry homework program. Dr. Grossman has also served two terms as one of the two faculty representatives on the UK Board of Trustees.
Inhaltsangabe
1 The Basics. 2 Polar Reactions under Basic Conditions. 3 Polar Reactions under Acidic Conditions. 4 Pericyclic Reactions. 5 Free-Radical Reactions. 6 Transition-Metal-Mediated and -Catalyzed Reactions. 7 Mixed-Mechanism Problems.

Chapter 1. The Basics.

1. Structure and Stability of Organic Compounds

o Conventions of Drawing Structures; Grossman's Rule

o Lewis Structures; Resonance Structures

o Molecular Shape; Hybridization

o Aromaticity

2. Bronsted Acidity and Basicity

o pKa Values

o Tautomerism

3. Kinetics and Thermodynamics

4. Getting Started at Drawing a Mechanism
o Reading and balancing organic reaction equations
o Determining which bonds are made and broken in a reaction

5. Classes of Overall Transformations

6. Classes of Mechanisms

o Polar Mechanisms

Nucleophiles

Electrophiles and Leaving Groups

Acidic and Basic Conditions; The pKa Rule

A Typical Polar Mechanism

o Free-Radical Mechanisms

o Pericyclic Mechanisms

o Transition-Metal-Catalyzed and -Mediated Mechanisms

7. Summary

8. End of Chapter Problems

Chapter 2. Polar Reactions under Basic Conditions.

1. Introduction to Substitution and Elimination

o Substitution by the SN2 Mechanism

o beta-Elimination by the E2 and E1cb Mechanisms

o Predicting Substitution vs. Elimination

2. Addition of Nucleophiles to Electrophilic pi Bonds

o Addition to Carbonyl Compounds

o Conjugate Addition; The Michael Reaction

3. Substitution at C(sp2)-X s Bonds

o Substitution at Carbonyl C

o Substitution at Alkenyl and Aryl C

o Metal Insertion; Halogen-Metal Exchange

4. Substitution and Elimination at C(sp3)-X s Bonds

o Substitution by the SRN1 Mechanism

o Substitution by the Elimination-Addition Mechanism

o Substitution by the One-Electron Transfer Mechanism

o Metal Insertion; Halogen-Metal Exchange

o -Elimination; Generation and Reactions of Carbenes

5. Base-Promoted Rearrangements

o Migrations from C to C

o Migrations from C to O
o Migrations from C to N

o Migrations from B to C or O

6. Two Multistep Reactions

o The Swern Oxidation

o The Mitsunobu Reaction

7. Summary

8. End of Chapter Problems

Chapter 3. Polar Reactions under Acidic Conditions.

1. Carbocations

o Carbocation Stability

o Carbocation Generation; The Role of Protonation

o Typical Reactions of Carbocations; Rearrangements

2. Substitution and beta-Elimination Reactions at C(sp3)-X

o Substitution by the SN1 and SN2 Mechanisms

o Elimination by the E1 Mechanism

o Predicting Substitution vs. Elimination

3. Electrophilic Addition to Nucleophilic C=C pi Bonds

4. Substitution at Nucleophilic C=C pi Bonds

o Electrophilic Aromatic Substitution

o Aromatic Substitution of Anilines via Diazonium Salts

o Electrophilic Aliphatic Substitution

5. Nucleophilic Addition to and Substitution at Electrophilic pi Bonds.

o Heteroatom Nucleophiles

o Carbon Nucleophiles

6. Catalysis Involving Iminium Ions

7. Summary

8. End of Chapter Problems

Chapter 4. Pericyclic Reactions.

1. Introduction

o Classes of Pericyclic Reactions

o Polyene MOs

2. Electrocyclic Reactions

o Typical Reactions

o Stereospecificity

o Stereoselectivity

3. Cycloadditions

o Typical Reactions

The Diels-Alder Reaction

Other Cycloadditions

o Regioselectivity

o Stereospecificity

o Stereoselectivity

4. Sigmatropic Rearrangements

o Typical Reactions

o Stereospecificity

o Stereoselectivity

5. Ene Reactions.

6. Summary
7. End of Chapter Problems

Chapter 5. Free Radical Reactions.

1. Free Radicals

o Stability

o Generation from Closed-Shell Species

o Typical Reactions

o Chain vs. Nonchain Mechanisms

2. Chain Free-Radical Reactions

o Substitution Reactions

o Addition and Fragmentation Reactions
Carbon-Heteroatom Bond-Forming Reactions
Carbon-Carbon Bond-Forming and -Cleaving Reactions

3. Nonchain Free-Radical Reactions

o Photochemical Reactions

o Reductions and Oxidations with Metals

Addition of H2 across pi Bonds

Reduction of C-X Bonds. Reductive Coupling

One-Electron Oxidations

o Cycloaromatizations

4. Miscellaneous Radical Reactions

o 1,2-Anionic Rearrangements; Lone-Pair Inversion

o Triplet Carbenes and Nitrenes

5. Summary
6. End of Chapter Problems

Chapter 6. Transition-Metal-Mediated and -Catalyzed Reactions.

1. Introduction to the Chemistry of Transition Metals

o Conventions of Drawing Structures

o Counting Electrons

Typical Ligands; Total Electron Count

Oxidation State and d Electron Count

o Typical Reactions

o Stoichiometric vs. Catalytic Mechanisms

2. Addition Reactions

o Late-Metal-Catalyzed Hydrogenation and Hydrometallation (Pd, Pt, Rh)

o Hydroformylation (Co, Rh)

o Hydrozirconation (Zr)

o Alkene Polymerization (Ti, Zr, Sc, and others)

o Cyclopropanation, Epoxidation, and Aziridination of Alkenes (Cu, Rh, Mn, Ti)

o Dihydroxylation and Aminohydroxylation of Alkenes (Os)

o Nucleophilic Addition to Alkenes and Alkynes (Hg, Pd)

o Conjugate Addition Reactions (Cu)

o Reductive Coupling Reactions (Ti, Zr)

o Pauson-Khand Reaction (Co)

o Dötz Reaction (Cr)

o Metal-Catalyzed Cycloaddition and Cyclotrimerization (Co, Ni, Rh)

3. Substitution Reactions

o Hydrogenolysis (Pd)

o Carbonylation of Alkyl Halides (Pd, Rh)

o Heck Reaction (Pd)

o Metal-Caatalyzed Nucleophilic Substitution Reactions: Kumada, Stille, Suzuki, Negishi, Buchwald-Hartwig, Sonogashira, and Ullmann Reactions (Ni, Pd, Cu)

o Allylic Substitution (Pd)

o Pd-Catalyzed Nucleophilic Substitution of Alkenes; Wacker Oxidation

o C-H Activation (Pd, Ru, Rh)

o Tebbe Reaction (Ti)

o Propargyl Substitution in Co-Alkyne Complexes

4. Rearrangement Reactions

o Alkene Isomerization (Rh)

o Olefin and Alkyne Metathesis (Ru, W, Mo, Ti)

5. Elimination Reactions

o Oxidation of Alcohols (Cr, Ru)

o Decarbonylation of Aldehydes (Rh)

6. Summary

7. End of Chapter Problems

Chapter 7. Mixed Mechanism Problems.

Rezensionen
From the reviews of the second edition:

"... Grossman's book differs from others in the scale of the worked examples. The number of problems incorporated into the text is extraordinary. The author provides the student a Web site that includes the detailed mechanisms for every problem in the book, each of which includes explanation and commentary, and the answer set, when printed, exceeds 250 pages! . . . In style, The Art of... is unique in that it does not read like a typical textbook. Instead, the feel is like that of having a personal tutor next to you walking you through the chemistry in a step-by-step fashion. The writing is clear, concise, engaging, and, at times, outright entertaining. The lively style includes "Common Error Alerts" that teach students what not to do and includes tips and advice on how to solve problems . . . The highest compliment a reviewer can give is to adopt the text that he reviews. The next advanced course I teach will use The Art of Writing Reasonable Reaction Mechanisms with the goal that students will be able to posit a plausible mechanism for any new reaction that they encounter. To those of you who have taught traditional physical organic chemistry out of the classic texts, I ask you to consider trying something, well... completely different. The Art of Writing Reasonable Reaction Mechanisms might just change the way you do things."

-Journal of Chemical Education

"The Art of Writing Reasonable Organic Reaction Mechanisms has an entirely different scope, dedicated to teaching the application of first principles to the construction of organic mechanisms. ... The number of problems incorporated into the text is extraordinary. The author provides the student a Web site that includes the detailed mechanisms for every problem in the book ... . The writing is clear, concise, engaging and, at times, outright entertaining. ... All sections are expertly written, well organized and up-to-date." (R. W. Holman, Journal of Chemical Education, Vol. 80 (11), 2003)

"In principle, most mechanisms are derived from a basis set of fundamental steps. ... Grossman has succeeded in explaining these fundamentals in detail in an easily accessible monograph. ... Readers can reinforce their incipient skills with practical illustrations, and are challenged throughout with complicated examples. ... the present text offers additional lucid explanations and ideal opportunities for practice. This work will thus be indispensable for students who are interested in mechanisms, or who wish to gain an additional perspective." (www.organische-chemie.ch, July, 2004)

"This text shows how to write a reasonable mechanism for an organic chemical transformation. ... It can be used either in a formal course or by students working on their own, and will be particularly useful for graduate students studying for qualifying examinations. It will also be useful to students and researchers in biochemistry, pharmacology, and inorganic chemistry." (Chimie Nouvelle, Vol. 84 (21), 2003)

"Robert Grossman in his book attempts to familiarize the student with the awesome power of reaction mechanisms ... . What makes this book special and praise-worthy is the clarity of its presentation of the subject matter. The text is lucid and sharp-edged throughout. The production quality of the book is first-class, too. Paper, printing and binding are excellent, the reproduction of the numerous formulae and reaction schemes is outstanding. ... Full marks for this 'survival guide' to the 'organic jungle'." (T. Lazar, Synthesis, Issue 17, 2003)

"The book entitled 'The Art of Writing Reasonable Organic Reaction Mechanisms' ... shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is the case in most textbooks. ... Each chapter is capped by a large problem set. ... The book will be useful to students and researchers in intermediate organic chemistry, biochemistry, pharmacology, and inorganic chemistry." (Process - Magazin für Chemietechnik, Vol. 6 (3), 2003)

"Robert Grossman discusses ideas on organic chemical reactivity, selectivity and structure in a logical way that gives the student confidence in attempting the many practice problems provided. ... This book provides a snapshot of examples of how to consider and approach the writing of simple and sophisticated examples of pushing electrons in and out of orbitals. Students will enormously benefit from using the principles and concepts in this book in writing their own mechanisms." (Helmut Hügel, Chemistry in Australia, 2003)

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