{"product_id":"the-art-of-writing-reasonable-organic-reaction-mechanisms-9783030287320","title":"The Art of Writing Reasonable Organic Reaction","description":"\u003cb\u003eBook Synopsis\u003c\/b\u003e\u003cbr\u003e\u003cp\u003eIntended 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.\u003c\/p\u003e\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTable of Contents\u003c\/b\u003e\u003cbr\u003e\u003cp\u003e\u003c\/p\u003e\u003cp\u003e\u003cb\u003eChapter 1. The Basics.\u003c\/b\u003e\u003c\/p\u003e  \u003cp\u003e1.     Structure and Stability of Organic Compounds\u003c\/p\u003e  \u003cp\u003eo    Conventions of Drawing Structures; Grossman's Rule\u003c\/p\u003e  \u003cp\u003eo    Lewis Structures; Resonance Structures\u003c\/p\u003e  o    Molecular Shape; Hybridization\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Aromaticity\u003c\/p\u003e  \u003cp\u003e2.     Bronsted Acidity and Basicity\u003c\/p\u003e  \u003cp\u003eo    p\u003ci\u003eK\u003c\/i\u003e\u003csub\u003ea\u003c\/sub\u003e Values\u003c\/p\u003e  \u003cp\u003eo    Tautomerism\u003c\/p\u003e  \u003cp\u003e3.     Kinetics and Thermodynamics\u003c\/p\u003e  4.     Getting Started at Drawing a Mechanism\u003cbr\u003eo      Reading and balancing organic reaction equations\u003cbr\u003eo      Determining which bonds are made and broken in a reaction\u003cbr\u003e\u003cp\u003e\u003c\/p\u003e  \u003cp\u003e5.     Classes of Overall Transformations\u003c\/p\u003e  \u003cp\u003e6.     Classes of Mechanisms \u003c\/p\u003e\u003cp\u003eo    Polar Mechanisms\u003cbr\u003e\u003c\/p\u003e\u003cp\u003e§  Nucleophiles\u003cbr\u003e\u003c\/p\u003e\u003cp\u003e§  Electrophiles and Leaving Groups\u003c\/p\u003e\u003cp\u003e§  Acidic and Basic Conditions; The p\u003ci\u003eK\u003c\/i\u003e\u003csub\u003ea\u003c\/sub\u003e Rule\u003cbr\u003e\u003c\/p\u003e\u003cp\u003e§  A Typical Polar Mechanism\u003c\/p\u003e\u003cp\u003eo    Free-Radical Mechanisms\u003c\/p\u003e\u003cp\u003e\u003c\/p\u003e\u003cp\u003eo    Pericyclic Mechanisms\u003cbr\u003e\u003c\/p\u003e\u003cp\u003eo    Transition-Metal-Catalyzed and -Mediated Mechanisms\u003c\/p\u003e  \u003cp\u003e7.     Summary\u003c\/p\u003e\u003cp\u003e8.    End of Chapter Problems\u003c\/p\u003e     \u003cp\u003e\u003cb\u003eChapter 2. Polar Reactions under Basic Conditions.\u003c\/b\u003e\u003c\/p\u003e  \u003cp\u003e1.    Introduction to Substitution and Elimination\u003c\/p\u003e  \u003cp\u003eo    Substitution by the S\u003csub\u003eN\u003c\/sub\u003e2 Mechanism\u003c\/p\u003e  o    β-Elimination by the E2 and E1cb Mechanisms\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Predicting Substitution vs. Elimination\u003c\/p\u003e  \u003cp\u003e2.     Addition of Nucleophiles to Electrophilic π Bonds\u003c\/p\u003e  \u003cp\u003eo    Addition to Carbonyl Compounds\u003c\/p\u003e  o    Conjugate Addition; The Michael Reaction\u003cp\u003e\u003c\/p\u003e  \u003cp\u003e3.     Substitution at C(sp\u003csup\u003e2\u003c\/sup\u003e)–X  \u003ci\u003es \u003c\/i\u003eBonds\u003c\/p\u003e  \u003cp\u003eo    Substitution at Carbonyl C\u003c\/p\u003e  \u003cp\u003eo    Substitution at Alkenyl and Aryl C\u003c\/p\u003e  \u003cp\u003eo    Metal Insertion; Halogen–Metal Exchange\u003c\/p\u003e  4.     Substitution and Elimination at C(sp\u003csup\u003e3\u003c\/sup\u003e)–X σ Bonds\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Substitution by the S\u003csub\u003eRN\u003c\/sub\u003e1 Mechanism\u003c\/p\u003e  \u003cp\u003eo    Substitution by the Elimination–Addition Mechanism\u003c\/p\u003e  \u003cp\u003eo    Substitution by the One-Electron Transfer Mechanism\u003c\/p\u003e  o    Metal Insertion; Halogen–Metal Exchange\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    α-Elimination; Generation and Reactions of Carbenes\u003c\/p\u003e  \u003cp\u003e5.     Base-Promoted Rearrangements\u003c\/p\u003e  \u003cp\u003eo    Migrations from C to C\u003c\/p\u003e  o    Migrations from C to O\u003cbr\u003eo    Migrations from C to \tN\u003cbr\u003e\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Migrations from B to C or O\u003c\/p\u003e  \u003cp\u003e6.     Two Multistep Reactions\u003c\/p\u003e  \u003cp\u003eo   The Swern Oxidation\u003c\/p\u003e  o   The Mitsunobu Reaction\u003cp\u003e\u003c\/p\u003e  \u003cp\u003e7.     Summary\u003c\/p\u003e\u003cp\u003e8.    End of Chapter Problems\u003cbr\u003e\u003c\/p\u003e\u003cp\u003e\u003cbr\u003e\u003c\/p\u003e     \u003cp\u003e\u003cb\u003eChapter 3. Polar Reactions under Acidic Conditions.\u003c\/b\u003e\u003c\/p\u003e  \u003cp\u003e1.     Carbocations\u003c\/p\u003e  o    Carbocation Stability\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Carbocation Generation; The Role of Protonation\u003c\/p\u003e  \u003cp\u003eo    Typical Reactions of Carbocations; Rearrangements\u003c\/p\u003e  \u003cp\u003e2.     Substitution and β-Elimination Reactions at C(sp\u003csup\u003e3\u003c\/sup\u003e)–X\u003c\/p\u003e  \u003cp\u003eo    Substitution by the S\u003csub\u003eN\u003c\/sub\u003e1 and S\u003csub\u003eN\u003c\/sub\u003e2 Mechanisms\u003c\/p\u003e  o    Elimination by the E1 Mechanism\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Predicting Substitution vs. Elimination\u003c\/p\u003e  \u003cp\u003e3.     Electrophilic Addition to Nucleophilic C=C π Bonds\u003c\/p\u003e  \u003cp\u003e4.     Substitution at Nucleophilic C=C π Bonds\u003c\/p\u003e  o    Electrophilic Aromatic Substitution\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Aromatic Substitution of Anilines via Diazonium Salts\u003c\/p\u003e  \u003cp\u003eo    Electrophilic Aliphatic Substitution\u003c\/p\u003e  \u003cp\u003e5.     Nucleophilic Addition to and Substitution at Electrophilic π Bonds.\u003c\/p\u003e  o    Heteroatom Nucleophiles\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Carbon Nucleophiles\u003c\/p\u003e  \u003cp\u003e6.     Catalysis Involving Iminium Ions\u003c\/p\u003e  \u003cp\u003e7.     Summary\u003c\/p\u003e\u003cp\u003e8.    End of Chapter Problems\u003cbr\u003e\u003c\/p\u003e     \u003cp\u003e\u003cb\u003eChapter 4. Pericyclic Reactions.\u003c\/b\u003e\u003c\/p\u003e  \u003cp\u003e1.     Introduction\u003c\/p\u003e  \u003cp\u003eo    Classes of Pericyclic Reactions\u003c\/p\u003e  \u003cp\u003eo    Polyene MOs\u003c\/p\u003e  2.     Electrocyclic Reactions\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Typical Reactions\u003c\/p\u003e  \u003cp\u003eo    Stereospecificity\u003c\/p\u003e  \u003cp\u003eo    Stereoselectivity \u003c\/p\u003e  3.     Cycloadditions\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Typical Reactions\u003c\/p\u003e  \u003cp\u003e§  The Diels–Alder Reaction\u003c\/p\u003e  \u003cp\u003e§  Other Cycloadditions\u003c\/p\u003e  o    Regioselectivity \u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Stereospecificity\u003c\/p\u003e  \u003cp\u003eo    Stereoselectivity \u003c\/p\u003e  \u003cp\u003e4.     Sigmatropic Rearrangements\u003c\/p\u003e  o    Typical Reactions\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Stereospecificity \u003c\/p\u003e  \u003cp\u003eo    Stereoselectivity\u003c\/p\u003e  \u003cp\u003e5.     Ene Reactions.\u003c\/p\u003e  6.     Summary\u003cbr\u003e7.    End of Chapter Problems\u003cbr\u003e\u003cp\u003e\u003c\/p\u003e     \u003cp\u003e\u003cb\u003eChapter 5. Free Radical Reactions.\u003c\/b\u003e\u003c\/p\u003e  \u003cp\u003e1.     Free Radicals\u003c\/p\u003e  \u003cp\u003eo    Stability\u003c\/p\u003e  \u003cp\u003eo    Generation from Closed-Shell Species\u003c\/p\u003e  o    Typical Reactions\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Chain vs. Nonchain Mechanisms\u003c\/p\u003e  \u003cp\u003e2.     Chain Free-Radical Reactions\u003c\/p\u003e  \u003cp\u003eo    Substitution Reactions\u003c\/p\u003e  o    Addition and Fragmentation Reactions\u003cbr\u003e§  Carbon-Heteroatom Bond-Forming Reactions\u003cbr\u003e§  Carbon-Carbon Bond-Forming and -Cleaving Reactions\u003cbr\u003e\u003cp\u003e\u003c\/p\u003e  \u003cp\u003e3.     Nonchain Free-Radical Reactions\u003c\/p\u003e  \u003cp\u003eo    Photochemical Reactions\u003c\/p\u003e  \u003cp\u003eo    Reductions and Oxidations with Metals\u003c\/p\u003e\u003cp\u003e§  Addition of H2 across π Bonds \u003c\/p\u003e\u003cp\u003e§  Reduction of C-X Bonds. Reductive Coupling\u003cbr\u003e\u003c\/p\u003e\u003cp\u003e§  One-Electron Oxidations\u003cbr\u003e\u003c\/p\u003e\u003cp\u003e o    Cycloaromatizations\u003c\/p\u003e\u003cp\u003e\u003c\/p\u003e  \u003cp\u003e4.     Miscellaneous Radical Reactions\u003c\/p\u003e  \u003cp\u003eo    1,2-Anionic Rearrangements; Lone-Pair Inversion\u003c\/p\u003e  \u003cp\u003eo    Triplet Carbenes and Nitrenes\u003c\/p\u003e  5.     Summary\u003cbr\u003e6.    End of Chapter Problems\u003cbr\u003e\u003cp\u003e\u003c\/p\u003e     \u003cp\u003e\u003cb\u003eChapter 6. Transition-Metal-Mediated and -Catalyzed Reactions.\u003c\/b\u003e\u003c\/p\u003e  \u003cp\u003e1.     Introduction to the Chemistry of Transition Metals\u003c\/p\u003e  \u003cp\u003eo    Conventions of Drawing Structures\u003c\/p\u003e  \u003cp\u003eo    Counting Electrons\u003c\/p\u003e  §  Typical Ligands; Total Electron Count\u003cp\u003e\u003c\/p\u003e  \u003cp\u003e§  Oxidation State and d Electron Count\u003c\/p\u003e  \u003cp\u003eo    Typical Reactions\u003c\/p\u003e  \u003cp\u003eo    Stoichiometric vs. Catalytic Mechanisms\u003c\/p\u003e  2.     Addition Reactions\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Late-Metal-Catalyzed Hydrogenation and Hydrometallation (Pd, Pt, Rh)\u003c\/p\u003e  \u003cp\u003eo    Hydroformylation (Co, Rh)\u003c\/p\u003e  \u003cp\u003eo    Hydrozirconation (Zr)\u003c\/p\u003e  o    Alkene Polymerization (Ti, Zr, Sc, and others)\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Cyclopropanation, Epoxidation, and Aziridination of Alkenes (Cu, Rh, Mn, Ti)\u003c\/p\u003e  \u003cp\u003eo    Dihydroxylation and Aminohydroxylation of Alkenes (Os)\u003c\/p\u003e  \u003cp\u003eo    Nucleophilic Addition to Alkenes and Alkynes (Hg, Pd)\u003c\/p\u003e  o    Conjugate Addition Reactions (Cu)\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Reductive Coupling Reactions (Ti, Zr)\u003c\/p\u003e  \u003cp\u003eo    Pauson–Khand Reaction (Co)\u003c\/p\u003e  \u003cp\u003eo    Dötz Reaction (Cr)\u003c\/p\u003e  o    Metal-Catalyzed Cycloaddition and Cyclotrimerization (Co, Ni, Rh)\u003cp\u003e\u003c\/p\u003e  \u003cp\u003e3.     Substitution Reactions\u003c\/p\u003e  \u003cp\u003eo    Hydrogenolysis (Pd)\u003c\/p\u003e\u003cp\u003eo    Carbonylation of Alkyl Halides (Pd, Rh)\u003c\/p\u003e\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Heck Reaction (Pd)\u003c\/p\u003e  \u003cp\u003eo    Metal-Caatalyzed Nucleophilic Substitution Reactions: Kumada, Stille, Suzuki, Negishi, Buchwald–Hartwig, Sonogashira, and Ullmann Reactions (Ni, Pd, Cu)\u003c\/p\u003e  \u003cp\u003eo    Allylic Substitution (Pd)\u003c\/p\u003e  \u003cp\u003eo    Pd-Catalyzed Nucleophilic Substitution of Alkenes; Wacker Oxidation\u003c\/p\u003e\u003cp\u003eo    C–H Activation (Pd, Ru, Rh)\u003cbr\u003e\u003c\/p\u003e  \u003cp\u003eo    Tebbe Reaction (Ti)\u003c\/p\u003e  o    Propargyl Substitution in Co–Alkyne Complexes\u003cp\u003e\u003c\/p\u003e  \u003cp\u003e4.     Rearrangement Reactions\u003c\/p\u003e  \u003cp\u003eo    Alkene Isomerization (Rh)\u003c\/p\u003e  \u003cp\u003eo    Olefin and Alkyne Metathesis (Ru, W, Mo, Ti)\u003c\/p\u003e  5.     Elimination Reactions\u003cp\u003e\u003c\/p\u003e  \u003cp\u003eo    Oxidation of Alcohols (Cr, Ru)\u003c\/p\u003e  \u003cp\u003eo    Decarbonylation of Aldehydes (Rh)\u003c\/p\u003e  \u003cp\u003e6.     Summary\u003c\/p\u003e\u003cp\u003e7.     End of Chapter Problems\u003c\/p\u003e     \u003cp\u003e\u003cb\u003eChapter 7. Mixed Mechanism Problems.\u003c\/b\u003e\u003c\/p\u003e\u003cbr\u003e\u003cp\u003e\u003c\/p\u003e","brand":"Springer Nature Switzerland AG","offers":[{"title":"Default Title","offer_id":50470468747607,"sku":"9783030287320","price":64.99,"currency_code":"GBP","in_stock":true}],"url":"https:\/\/bookcurl.com\/products\/the-art-of-writing-reasonable-organic-reaction-mechanisms-9783030287320","provider":"Book Curl","version":"1.0","type":"link"}