Foreword |
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xi | |
Inspiration |
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xv | |
Acknowledgements |
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xvii | |
Additional Resources |
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xix | |
Style and Substance |
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xxi | |
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SECTION 1 LAYING THE FOUNDATIONS |
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1 | (2) |
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Basics 1 Structures of Organic Compounds |
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3 | (10) |
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Habit 1 Always Draw Structures with Realistic Geometry |
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11 | (2) |
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Basics 2 Functional Groups and `R' Groups |
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13 | (6) |
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Basics 3 Naming Organic Compounds |
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19 | (10) |
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Practice 1 Drawing Structures from Chemical Names |
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26 | (3) |
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Basics 4 Isomerism in Organic Chemistry-Constitutional Isomers |
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29 | (15) |
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Practice 2 Constitutional Isomers and Chemical Names |
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31 | (2) |
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Habit 2 Identifying When a Formula is Possible |
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33 | (3) |
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Practice 3 Double Bond Equivalents |
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36 | (3) |
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Common Error 1 Formulae, Functional Groups, and Double Bond Equivalents |
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39 | (3) |
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Habit 3 Ignore What Doesn't Change |
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42 | (2) |
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Basics 5 Electronegativity, Bond Polarization, and Inductive Effects |
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44 | (4) |
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Practice 4 Bond Polarization and Electronegativity |
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46 | (2) |
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Basics 6 Bonding in Organic Compounds |
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48 | (14) |
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59 | (3) |
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Basics 7 Bonding and Antibonding Orbitals |
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62 | (3) |
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Basics 8 Introduction to Curly Arrows |
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65 | (18) |
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Fundamental Reaction Type 1 Nucleophilic Substitution at Saturated Carbon |
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72 | (4) |
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Practice 6 Electronegativity in Context |
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76 | (2) |
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Fundamental Reaction Type 2 Elimination Reactions |
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78 | (5) |
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SECTION 2 BUILDING ON THE FOUNDATIONS |
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83 | (2) |
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Basics 9 Breaking Bonds-Linking Curly Arrows and Molecular Orbitals |
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85 | (10) |
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Common Error 2 Curly Arrows |
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93 | (2) |
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Basics 10 Conjugation and Resonance |
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95 | (10) |
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Basics 11 Thermodynamic Definitions |
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105 | (3) |
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Basics 12 Bond Dissociation Energy |
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108 | (3) |
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Basics 13 Calculating Enthalpy of Reaction from Bond Dissociation Energies |
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111 | (12) |
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Perspective 1 A Closer Look at Bond Dissociation Energies |
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114 | (4) |
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Practice 7 Calculating Enthalpy of Reaction from Bond Dissociation Energy |
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118 | (5) |
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Basics 14 Energetics and Reaction Profiles |
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123 | (5) |
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Basics 15 How Fast Are Reactions? |
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128 | (3) |
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Basics 16 Introduction to Carbocations, Carbanions, and Free-Radicals |
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131 | (9) |
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Basics 17 Carbocations 2-More Factors Affecting Stability |
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140 | (8) |
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Basics 18 Carbanions 2-Stability and pKa |
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148 | (31) |
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Perspective 2 A Scale for Carbocation Stability |
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159 | (8) |
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Common Error 3 Methyl Groups are Electron-Releasing |
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167 | (3) |
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Practice 8 Drawing Resonance Forms for Carbocations and Carbanions |
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170 | (6) |
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176 | (3) |
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Basics 19 The Hammond Postulate |
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179 | (4) |
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Basics 20 Conjugation and Stability-The Evidence |
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183 | (6) |
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Common Error 5 Carbocations and Carbanions |
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187 | (2) |
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Basics 21 Reactivity of Conjugated Systems |
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189 | (2) |
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Basics 22 Acid Catalysis in Organic Reactions Part 1 |
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191 | (18) |
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Reaction Detail 1 Nucleophilic Substitution at Saturated Carbon |
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196 | (13) |
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Basics 23 What Defines a Transition State? |
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209 | (14) |
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Perspective 3 Bonding Beyond Hybridization |
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212 | (9) |
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Fundamental Knowledge Recap 1 Bond Lengths and Strengths |
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221 | (1) |
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Fundamental Knowledge Recap 2 pKa |
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222 | (1) |
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SECTION 3 A FOCUS ON SHAPE |
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223 | (5) |
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Habit 4 Representing Stereochemistry-Flying Wedge and Newman Projections |
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225 | (3) |
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Basics 24 Isomerism in Organic Chemistry-Configurational Isomers |
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228 | (32) |
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Habit 5 Getting Used to Drawing Stereoisomers |
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232 | (8) |
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Practice 9 Getting Used to Stereoisomers |
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240 | (3) |
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Habit 6 Assignments of Stereochemsitry--The Cahn-Ingold-Prelog Rules |
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243 | (11) |
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Practice 10 Assigning Stereochemistry |
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254 | (2) |
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Habit 7 Stereoisomers with Symmetry |
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256 | (4) |
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Basics 25 Properties of Stereoisomers |
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260 | (19) |
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Reaction Detail 2 Stereochemical Aspects of Substitution Reactions |
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263 | (8) |
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Common Error 6 Substitution Reactions |
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271 | (2) |
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Reaction Detail 3 Substitution with Retention of Configuration |
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273 | (2) |
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Common Error 7 Stereochemical Errors |
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275 | (4) |
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SECTION 4 TYPES OF SELECTIVITY |
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279 | (2) |
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Basics 26 Selectivity in Organic Chemistry-Chemoselectivity |
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281 | (1) |
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Basics 27 Selectivity in Organic Chemistry-Regioselectivity |
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282 | (1) |
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Basics 28 Selectivity in Organic Chemistry-Stereoselectivity |
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283 | (7) |
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Basics 29 Stereochemical Definitions Relating to Reactions |
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290 | (5) |
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SECTIONS 5 BONDS CAN ROTATE |
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293 | (2) |
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Basics 30 Isomerism in Organic Chemistry-Conformational Isomers |
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295 | (20) |
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Practice 11 Conformational Analysis |
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300 | (3) |
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Applications 1 Conformational Isomers 2 |
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303 | (5) |
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Applications 2 SN2 Substitution Reactions Forming Three-Membered Rings |
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308 | (7) |
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Basics 31 Introduction to Cyclohexanes |
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315 | (20) |
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Practice 12 Drawing Cyclohexanes |
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326 | (3) |
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Applications 3 Substitution Reactions of Cyclohexanes |
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329 | (6) |
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Basics 32 Quantifying Conformers of Cyclohexanes |
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335 | (7) |
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Basics 33 More Conformers of Cyclohexanes and Related Compounds |
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342 | (11) |
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Practice 13 Drawing More Complex Cyclohexanes |
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347 | (3) |
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Common Error 8 Cyclohexanes |
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350 | (3) |
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SECTION 6 ELIMINATING THE LEARNING |
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353 | (5) |
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Reaction Detail 4 Elimination Reactions |
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358 | (6) |
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Perspective 4 A Continuum of Mechanisms |
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364 | (4) |
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Basics 34 More Substituted Alkenes Are More Stable |
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368 | (4) |
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Basics 35 Enthalpy Changes for Reactions Involving Anionic Species |
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372 | (2) |
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Applications 4 Stereochemistry of Elimination Reactions |
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375 | (6) |
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Basics 36 Stereospecificity |
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381 | (2) |
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Applications 5 Elimination Reactions of Cyclohexanes |
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383 | (7) |
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Common Error 9 Elimination Reactions |
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390 | (1) |
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Reaction Detail 5 Allylic Substitution |
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391 | (6) |
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SECTION 7 BUILDING SKILLS |
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397 | (2) |
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Worked Problem 1 Curly Arrows and Reaction Profiles |
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399 | (4) |
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Worked Problem 2 Competing SN1 Substitution and E1 Elimination |
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403 | (3) |
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Worked Problem 3 Competing SN2 Substitution and E2 Elimination |
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406 | (4) |
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Worked Problem 4 Acid Catalysis in Organic Reactions Part 2 |
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410 | (4) |
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Worked Problem 5 Epoxide Opening Reactions |
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414 | (3) |
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Worked Problem 6 Is cis-Cyclohexane-1, 2-diol Really Achiral? |
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417 | (2) |
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Worked Problem 7 The Furst-Plattner Rule |
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419 | (4) |
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Worked Problem 8 SN2' Stereochemistry and Conformations |
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423 | (3) |
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Worked Problem 9 Complex Substitution Stereochemistry |
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426 | (4) |
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Worked Problem 10 Cyclization Reactions |
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430 | (4) |
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Solution to Problem 1 Curly Arrows and Reaction Profiles |
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434 | (4) |
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Solution to Problem 2 Competing SN1 Substitution and El Elimination |
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438 | (6) |
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Solution to Problem 3 Competing SN2 Substitution and E2 Elimination |
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444 | (5) |
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Solution to Problem 4 Acid Catalysis in Organic Reactions Part 2 |
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449 | (5) |
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Solution to Problem 5 Epoxide Opening Reactions |
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454 | (3) |
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Solution to Problem 6 Is cis-Cyclohexane-1,2-diol Really Achiral? |
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457 | (4) |
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Solution to Problem 7 The Furst-Plattner Rule |
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461 | (9) |
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Solution to Problem 8 SN2' Stereochemistry and Conformations |
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470 | (6) |
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Solution to Problem 9 Complex Substitution Stereochemistry |
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476 | (6) |
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Solution to Problem 10 Cyclization Reactions |
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482 | (5) |
Afterword |
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487 | (2) |
Index |
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489 | |