
The Art of Writing Reasonable Organic Reaction Mechanisms
Hardcover | 1 December 2002 | Edition Number 2
At a Glance
374 Pages
Revised
23.39 x 15.6 x 2.24
Hardcover
$129.00
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Industry Reviews
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 andup-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 thecase 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 fuer 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 Huegel, Chemistry in Australia, 2003)
| Preface to the Student | p. v |
| Preface to the Instructor | p. ix |
| The Basics | p. 1 |
| Structure and Stability of Organic Compounds | p. 1 |
| Conventions of Drawing Structures; Grossman's Rule | p. 1 |
| Lewis Structures; Resonance Structures | p. 3 |
| Molecular Shape; Hybridization | p. 9 |
| Aromaticity | p. 13 |
| Bronsted Acidity and Basicity | p. 16 |
| pK[subscript a] Values | p. 16 |
| Tautomerism | p. 19 |
| Kinetics and Thermodynamics | p. 20 |
| Getting Started in Drawing a Mechanism | p. 22 |
| Classes of Overall Transformations | p. 25 |
| Classes of Mechanisms | p. 26 |
| Polar Mechanisms | p. 27 |
| Free-Radical Mechanisms | p. 38 |
| Pericyclic Mechanisms | p. 41 |
| Transition-Metal-Catalyzed and -Mediated Mechanisms | p. 42 |
| Summary | p. 42 |
| Problems | p. 43 |
| Polar Reactions under Basic Conditions | p. 50 |
| Substitution and Elimination at C(sp[superscript 3])-X [sigma] Bonds, Part I | p. 50 |
| Substitution by the S[subscript N]2 Mechanism | p. 51 |
| [beta]-Elimination by the E2 and Elcb Mechanisms | p. 53 |
| Predicting Substitution vs. Elimination | p. 56 |
| Addition of Nucleophiles to Electrophilic [pi] Bonds | p. 58 |
| Addition to Carbonyl Compounds | p. 58 |
| Conjugate Addition; The Michael Reaction | p. 67 |
| Substitution at C(sp[superscript 2])-X [sigma] Bonds | p. 69 |
| Substitution at Carbonyl C | p. 69 |
| Substitution at Alkenyl and Aryl C | p. 74 |
| Metal Insertion; Halogen-Metal Exchange | p. 78 |
| Substitution and Elimination at C(sp[superscript 3])-X [sigma] Bonds, Part II | p. 80 |
| Substitution by the S[subscript RN]1 Mechanism | p. 80 |
| Substitution by the Elimination-Addition Mechanism | p. 81 |
| Substitution by the One-Electron Transfer Mechanism | p. 82 |
| Metal Insertion; Halogen-Metal Exchange | p. 83 |
| [alpha]-Elimination; Generation and Reactions of Carbenes | p. 84 |
| Base-Promoted Rearrangements | p. 87 |
| Migration from C to C | p. 88 |
| Migration from C to O or N | p. 90 |
| Migration from B to C or O | p. 91 |
| Two Multistep Reactions | p. 92 |
| The Swern Oxidation | p. 92 |
| The Mitsunobu Reaction | p. 94 |
| Summary | p. 95 |
| Problems | p. 97 |
| Polar Reactions Under Acidic Conditions | p. 105 |
| Carbocations | p. 105 |
| Carbocation Stability | p. 106 |
| Carbocation Generation; The Role of Protonation | p. 109 |
| Typical Reactions of Carbocations; Rearrangements | p. 112 |
| Substitution and [beta]-Elimination Reactions at C(sp[superscript 3])-X | p. 117 |
| Substitution by the S[subscript N]1 and S[subscript N]2 Mechanisms | p. 117 |
| [beta]-Elimination by the E1 Mechanism | p. 120 |
| Predicting Substitution vs. Elimination | p. 122 |
| Electrophilic Addition to Nucleophilic C=C [pi] Bonds | p. 122 |
| Substitution at Nucleophilic C=C [pi] Bonds | p. 125 |
| Electrophilic Aromatic Substitution | p. 125 |
| Aromatic Substitution of Anilines via Diazonium Salts | p. 129 |
| Electrophilic Aliphatic Substitution | p. 131 |
| Nucleophilic Addition to and Substitution at Electrophilic [pi] Bonds | p. 132 |
| Heteroatom Nucleophiles | p. 132 |
| Carbon Nucleophiles | p. 136 |
| Summary | p. 140 |
| Problems | p. 141 |
| Pericyclic Reactions | p. 148 |
| Introduction | p. 148 |
| Classes of Pericyclic Reactions | p. 148 |
| Polyene MOs | p. 154 |
| Electrocyclic Reactions | p. 156 |
| Typical Reactions | p. 156 |
| Stereospecificity | p. 163 |
| Stereoselectivity | p. 168 |
| Cycloadditions | p. 170 |
| Typical Reactions | p. 170 |
| Regioselectivity | p. 183 |
| Stereospecificity | p. 184 |
| Stereoselectivity | p. 191 |
| Sigmatropic Rearrangements | p. 195 |
| Typical Reactions | p. 195 |
| Stereospecificity | p. 201 |
| Stereoselectivity | p. 206 |
| Ene Reactions | p. 210 |
| Summary | p. 213 |
| Problems | p. 215 |
| Free-Radical Reactions | p. 224 |
| Free Radicals | p. 224 |
| Stability | p. 224 |
| Generation from Closed-Shell Species | p. 227 |
| Typical Reactions | p. 232 |
| Chain vs. Nonchain Mechanisms | p. 238 |
| Chain Free-Radical Reactions | p. 239 |
| Substitution Reactions | p. 239 |
| Addition and Fragmentation Reactions | p. 244 |
| Nonchain Free-Radical Reactions | p. 252 |
| Photochemical Reactions | p. 252 |
| Reductions and Oxidations with Metals | p. 254 |
| Cycloaromatizations | p. 261 |
| Miscellaneous Radical Reactions | p. 261 |
| 1,2-Anionic Rearrangements; Lone-Pair Inversion | p. 261 |
| Triplet Carbenes and Nitrenes | p. 262 |
| Summary | p. 264 |
| Problems | p. 264 |
| Transition-Metal-Mediated and -Catalyzed Reactions | p. 270 |
| Introduction to the Chemistry of Transition Metals | p. 270 |
| Conventions of Drawing Structures | p. 270 |
| Counting Electrons | p. 271 |
| Typical Reactions | p. 276 |
| Stoichiometric vs. Catalytic Mechanisms | p. 282 |
| Addition Reactions | p. 283 |
| Late-Metal-Catalyzed Hydrogenation and Hydrometallation (Pd, Pt, Rh) | p. 283 |
| Hydroformylation (Co, Rh) | p. 286 |
| Hydrozirconation (Zr) | p. 287 |
| Alkene Polymerization (Ti, Zr, Sc, and others) | p. 288 |
| Cyclopropanation, Epoxidation, and Aziridination of Alkenes (Cu, Rh, Mn, Ti) | p. 290 |
| Dihydroxylation and Aminohydroxylation of Alkenes (Os) | p. 292 |
| Nucleophilic Addition to Alkenes and Alkynes (Hg, Pd) | p. 294 |
| Conjugate Addition Reactions (Cu) | p. 297 |
| Reductive Coupling Reactions (Ti, Zr) | p. 297 |
| Pauson-Khand Reaction (Co) | p. 301 |
| Dotz Reaction (Cr) | p. 303 |
| Metal-Catalyzed Cycloaddition and Cyclotrimerization (Co, Ni, Rh) | p. 306 |
| Substitution Reactions | p. 309 |
| Hydrogenolysis (Pd) | p. 309 |
| Carbonylation of Alkyl Halides (Pd, Rh) | p. 311 |
| Heck Reaction (Pd) | p. 313 |
| Coupling Reactions Between Nucleophiles and C(sp[superscript 2])-X: Kumada, Stille, Suzuki, Negishi, Buchwald-Hartwig, Sonogashira, and Ullmann Reactions (Ni, Pd, Cu) | p. 314 |
| Allylic Substitution (Pd) | p. 318 |
| Pd-Catalyzed Nucleophilic Substitution of Alkenes; Wacker Oxidation | p. 319 |
| Tebbe Reaction (Ti) | p. 321 |
| Propargyl Substitution in Co-Alkyne Complexes | p. 322 |
| Rearrangement Reactions | p. 323 |
| Alkene Isomerization (Rh) | p. 323 |
| Olefin and Alkyne Metathesis (Ru, W, Mo, Ti) | p. 323 |
| Elimination Reactions | p. 326 |
| Oxidation of Alcohols (Cr, Ru) | p. 326 |
| Decarbonylation of Aldehydes (Rh) | p. 326 |
| Summary | p. 327 |
| Problems | p. 328 |
| Mixed-Mechanism Problems | p. 334 |
| A Final Word | p. 339 |
| Index | p. 341 |
| Table of Contents provided by Rittenhouse. All Rights Reserved. |
ISBN: 9780387954684
ISBN-10: 0387954686
Published: 1st December 2002
Format: Hardcover
Language: English
Number of Pages: 374
Audience: General Adult
Publisher: Springer Nature B.V.
Country of Publication: GB
Edition Number: 2
Edition Type: Revised
Dimensions (cm): 23.39 x 15.6 x 2.24
Weight (kg): 0.68
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