Arrow-Pushing in Organic Chemistry

1 - Title Page [Seite 5]
2 - Copyright Page [Seite 6]
3 - Contents [Seite 9]
4 - Preface [Seite 13]
5 - Acknowledgements [Seite 15]
6 - About the Author [Seite 17]
7 - Chapter 1 Introduction [Seite 19]
7.1 - 1.1 DEFINITION OF ARROW?PUSHING [Seite 19]
7.2 - 1.2 FUNCTIONAL GROUPS [Seite 23]
7.3 - 1.3 NUCLEOPHILES AND LEAVING GROUPS [Seite 25]
7.4 - 1.4 SUMMARY [Seite 26]
7.5 - PROBLEMS [Seite 27]
8 - Chapter 2 Free Radicals [Seite 37]
8.1 - 2.1 WHAT ARE FREE RADICALS? [Seite 37]
8.2 - 2.2 HOW ARE FREE RADICALS FORMED? [Seite 39]
8.2.1 - 2.2.1 Free Radical Initiators [Seite 40]
8.2.2 - 2.2.2 Electron Transfer [Seite 41]
8.3 - 2.3 FREE RADICAL STABILITY [Seite 41]
8.4 - 2.4 WHAT TYPES OF REACTIONS INVOLVE FREE RADICALS? [Seite 43]
8.4.1 - 2.4.1 Halogenation Reactions [Seite 44]
8.4.2 - 2.4.2 Polymerization Reactions [Seite 46]
8.4.3 - 2.4.3 Oxidation Reactions [Seite 48]
8.5 - 2.5 SUMMARY [Seite 49]
8.6 - PROBLEMS [Seite 50]
9 - Chapter 3 Acids [Seite 55]
9.1 - 3.1 WHAT ARE ACIDS? [Seite 55]
9.2 - 3.2 WHAT IS RESONANCE? [Seite 56]
9.3 - 3.3 HOW IS ACIDITY MEASURED? [Seite 59]
9.4 - 3.4 RELATIVE ACIDITIES [Seite 60]
9.5 - 3.5 INDUCTIVE EFFECTS [Seite 65]
9.6 - 3.6 INDUCTIVE EFFECTS AND RELATIVE ACIDITIES [Seite 67]
9.7 - 3.7 RELATIVE ACIDITIES OF HYDROCARBONS [Seite 68]
9.8 - 3.8 SUMMARY [Seite 69]
9.9 - PROBLEMS [Seite 70]
10 - Chapter 4 Bases and Nucleophiles [Seite 79]
10.1 - 4.1 WHAT ARE BASES? [Seite 79]
10.2 - 4.2 WHAT ARE NUCLEOPHILES? [Seite 84]
10.3 - 4.3 LEAVING GROUPS [Seite 88]
10.4 - 4.4 SUMMARY [Seite 88]
10.5 - PROBLEMS [Seite 89]
11 - Chapter 5 SN2 Substitution Reactions [Seite 99]
11.1 - 5.1 WHAT IS AN SN2 REACTION? [Seite 99]
11.2 - 5.2 WHAT ARE LEAVING GROUPS? [Seite 101]
11.3 - 5.3 WHERE CAN SN2 REACTIONS OCCUR? [Seite 102]
11.4 - 5.4 SN2? REACTIONS [Seite 103]
11.5 - 5.5 SUMMARY [Seite 106]
11.6 - PROBLEMS [Seite 107]
12 - Chapter 6 SN1 Substitution Reactions [Seite 115]
12.1 - 6.1 WHAT IS AN SN1 REACTION? [Seite 115]
12.2 - 6.2 HOW ARE SN1 REACTIONS INITIATED? [Seite 116]
12.3 - 6.3 THE CARBOCATION [Seite 117]
12.3.1 - 6.3.1 Molecular Structure and Orbitals [Seite 118]
12.3.2 - 6.3.2 Stability of Carbocations [Seite 121]
12.4 - 6.4 CARBOCATION REARRANGEMENTS [Seite 123]
12.4.1 - 6.4.1 1,2?Hydride Shifts [Seite 123]
12.4.2 - 6.4.2 1,2?Alkyl Shifts [Seite 124]
12.4.3 - 6.4.3 Preventing Side Reactions [Seite 127]
12.5 - 6.5 SUMMARY [Seite 127]
12.6 - PROBLEMS [Seite 128]
13 - Chapter 7 Elimination Reactions [Seite 133]
13.1 - 7.1 E1 ELIMINATIONS [Seite 133]
13.2 - 7.2 E1cB ELIMINATIONS [Seite 136]
13.3 - 7.3 E2 ELIMINATIONS [Seite 138]
13.4 - 7.4 HOW DO ELIMINATION REACTIONS WORK? [Seite 139]
13.5 - 7.5 E1cB ELIMINATIONS VERSUS E2 ELIMINATIONS [Seite 142]
13.6 - 7.6 SUMMARY [Seite 142]
13.7 - PROBLEMS [Seite 144]
14 - Chapter 8 Addition Reactions [Seite 151]
14.1 - 8.1 ADDITION OF HALOGENS TO DOUBLE BONDS [Seite 151]
14.2 - 8.2 MARKOVNIKOV'S RULE [Seite 153]
14.3 - 8.3 ADDITIONS TO CARBONYLS [Seite 155]
14.3.1 - 8.3.1 1,2?Additions [Seite 155]
14.3.2 - 8.3.2 1,4?Additions [Seite 156]
14.3.3 - 8.3.3 Addition-Elimination Reactions [Seite 159]
14.4 - 8.4 SUMMARY [Seite 161]
14.5 - PROBLEMS [Seite 162]
15 - Chapter 9 Carbenes [Seite 171]
15.1 - 9.1 WHAT ARE CARBENES? [Seite 171]
15.2 - 9.2 HOW ARE CARBENES FORMED? [Seite 172]
15.3 - 9.3 REACTIONS WITH CARBENES [Seite 174]
15.3.1 - 9.3.1 Carbene Dimerization [Seite 174]
15.3.2 - 9.3.2 Cyclopropanation Reactions [Seite 175]
15.3.3 - 9.3.3 O-H Insertion Reactions [Seite 179]
15.4 - 9.4 CARBENES VERSUS CARBENOIDS [Seite 180]
15.5 - 9.5 SUMMARY [Seite 181]
15.6 - PROBLEMS [Seite 182]
16 - Chapter 10 Pericyclic Reactions [Seite 189]
16.1 - 10.1 WHAT ARE PERICYCLIC REACTIONS? [Seite 189]
16.2 - 10.2 ELECTROCYCLIC REACTIONS [Seite 190]
16.3 - 10.3 CYCLOADDITION REACTIONS [Seite 193]
16.3.1 - 10.3.1 The Diels-Alder Reaction [Seite 193]
16.3.2 - 10.3.2 The Ene Reaction [Seite 196]
16.3.3 - 10.3.3 Dipolar Cycloaddition Reactions [Seite 198]
16.4 - 10.4 SIGMATROPIC REACTIONS [Seite 200]
16.4.1 - 10.4.1 The Cope Rearrangement [Seite 201]
16.4.2 - 10.4.2 The Claisen Rearrangement [Seite 202]
16.5 - 10.5 SUMMARY [Seite 205]
16.6 - PROBLEMS [Seite 207]
17 - Chapter 11 Moving Forward [Seite 213]
17.1 - 11.1 FUNCTIONAL GROUP MANIPULATIONS [Seite 213]
17.2 - 11.2 NAME REACTIONS [Seite 214]
17.3 - 11.3 REAGENTS [Seite 226]
17.4 - 11.4 FINAL COMMENTS [Seite 226]
17.5 - PROBLEMS [Seite 227]
18 - Appendix 1 pKa Values of Protons Associated with Common Functional Groups [Seite 237]
19 - Appendix 2 Answers and Explanations to Problems [Seite 241]
20 - Appendix 3 Student Reaction Glossary [Seite 387]
21 - Index [Seite 391]
22 - Periodic Table of Elements [Seite 419]
23 - EULA [Seite 420]