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A guidebook to Mechanism in organic chemistry 6 edition by Peter Sypes

A guidebook to Mechanism in organic chemistry 6 edition by Peter Sypes

A guidebook to Mechanism in organic chemistry 6 edition by Peter Sypes

MARCH’S ADVANCED ORGANIC CHEMISTRY

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<span style="font-size: x-large;">Free chemistry book download :March's Advanced Organic Chemistry 6th Edition</span></h2>
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Free chemistry book download :March's Advanced Organic Chemistry 6th Edition

Advanced Organic Chemistry-Part A: Structure and Mechanisms

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Advanced Organic Chemistry-Part A: Structure and Mechanisms

Chemistry and creativity : Advanced Organic Chemistry-Part A: Structure and Mechanisms

Advanced Organic Chemistry PartB - Reaction and Synthesis

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<span style="font-size: x-large;">Advanced Organic Chemistry PartB - Reaction and Synthesis by Francis A. Carey and Richard J. Sundberg</span></h2>
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<br /></div>
<h3>
<span style="font-size: small;">Advanced Organic Chemistry PartB - Reaction and Synthesis</span></h3>
<div>
<div>
EDITION</div>
<div>
Part B: <b>Reactions and Synthesis</b></div>
<div>
<div>
<b>Advanced Organic Chemistry</b></div>
<div>
PART A: <b>Structure and Mechanisms</b></div>
<div>
PART B: <b>Reactions and Synthesis</b></div>
</div>
<div>
</div>
</div>
<div>
<br /></div>
<div>
<div>
The focus of Part B is on the closely interrelated topics of <b>reactions and synthesis</b>. In</div>
<div>
each of the first twelve chapters, we consider a group of related reactions that have</div>
<div>
been chosen for discussion primarily on the basis of their usefulness in synthesis. For</div>
<div>
each reaction we present an outline of the mechanism, its regio- and <b>stereochemical</b></div>
<div>
characteristics, and information on typical reaction conditions. For the more commonly</div>
<div>
used <b>reactions</b>, the schemes contain several examples, which may include examples of</div>
<div>
the <b>reaction </b>in relatively simple molecules and in more complex structures. The goal of</div>
<div>
these chapters is to develop a fundamental base of knowledge about organic reactions</div>
<div>
in the context of <b>synthesis</b>. We want to be able to answer questions such as: What</div>
<div>
transformation does a reaction achieve? What is the mechanism of the reaction? What</div>
<div>
reagents and reaction conditions are typically used? What substances can catalyze</div>
<div>
the reaction? How sensitive is the reaction to other functional groups and the steric</div>
<div>
environment? What factors control the stereoselectivity of the <b>reaction</b>? Under what</div>
<div>
conditions is the reaction enantioselective?</div>
<div>
<b>Synthesis </b>is the application of one or more reactions to the preparation of a</div>
<div>
particular target compound, and can pertain to a single-step transformation or to a</div>
<div>
number of sequential steps. The selection of a reaction or series of reactions for a</div>
<div>
synthesis involves making a judgment about the most effective possibility among</div>
<div>
the available options. There may be a number of possibilities for the synthesis of a</div>
<div>
particular compound. For example, in the course of learning about the reactions in</div>
<div>
Chapter 1 to 12, we will encounter a number of ways of making ketones, as outlined</div>
<div>
in the scheme that follows.</div>
</div>
<div>
<br /></div>
<div>
<div>
Chapter 1. Alkylation of Enolates and Other Carbon Nucleophiles . . . . . . 1</div>
<div>
Introduction........................................................................................................... 1</div>
<div>
1.1. Generation and Properties of Enolates and Other Stabilized Carbanions... 2</div>
<div>
1.1.1. Generation of Enolates by Deprotonation ........................................ 2</div>
<div>
1.1.2. Regioselectivity and Stereoselectivity in Enolate Formation</div>
<div>
from Ketones and Esters ................................................................... 5</div>
<div>
1.1.3. Other Means of Generating Enolates................................................ 14</div>
<div>
1.1.4. Solvent Effects on Enolate Structure and Reactivity ....................... 17</div>
<div>
1.2. Alkylation of Enolates.................................................................................. 21</div>
<div>
1.2.1. Alkylation of Highly Stabilized Enolates ......................................... 21</div>
<div>
1.2.2. Alkylation of Ketone Enolates.......................................................... 24</div>
<div>
1.2.3. Alkylation of Aldehydes, Esters, Carboxylic Acids, Amides,</div>
<div>
and Nitriles ........................................................................................ 31</div>
<div>
1.2.4. Generation and Alkylation of Dianions............................................ 36</div>
<div>
1.2.5. Intramolecular Alkylation of Enolates.............................................. 36</div>
<div>
1.2.6. Control of Enantioselectivity in Alkylation Reactions..................... 41</div>
<div>
1.3. The Nitrogen Analogs of Enols and Enolates: Enamines</div>
<div>
and Imine Anions ......................................................................................... 46</div>
<div>
General References............................................................................................... 55</div>
<div>
Problems ............................................................................................................... 56</div>
</div>
<div>
<div>
Chapter 2. Reactions of Carbon Nucleophiles</div>
<div>
with Carbonyl Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 63</div>
<div>
Introduction........................................................................................................... 63</div>
<div>
2.1. Aldol Addition and Condensation Reactions............................................... 64</div>
<div>
2.1.1. The General Mechanism ................................................................... 64</div>
<div>
2.1.2. Control of Regio- and Stereoselectivity of Aldol Reactions</div>
<div>
of Aldehydes and Ketones ................................................................ 65</div>
<div>
2.1.3. Aldol Addition Reactions of Enolates of Esters</div>
<div>
and Other Carbonyl Derivatives ....................................................... 78</div>
<div>
2.1.4. The Mukaiyama Aldol Reaction....................................................... 82</div>
<div>
2.1.5. Control of Facial Selectivity in Aldol and Mukaiyama Aldol</div>
<div>
Reactions............................................................................................ 86</div>
<div>
2.1.6. Intramolecular Aldol Reactions and the Robinson Annulation ....... 134</div>
<div>
2.2. Addition Reactions of Imines and Iminium Ions ........................................ 139</div>
<div>
2.2.1. The Mannich Reaction ...................................................................... 140</div>
<div>
2.2.2. Additions to N-Acyl Iminium Ions ................................................... 145</div>
<div>
2.2.3. Amine-Catalyzed Condensation Reactions....................................... 147</div>
<div>
2.3. Acylation of Carbon Nucleophiles............................................................... 148</div>
<div>
2.3.1. Claisen and Dieckmann Condensation Reactions ............................ 149</div>
<div>
2.3.2. Acylation of Enolates and Other Carbon Nucleophiles ................... 150</div>
<div>
2.4. Olefination Reactions of Stabilized Carbon Nucleophiles .......................... 157</div>
<div>
2.4.1. The Wittig and Related Reactions of Phosphorus-Stabilized</div>
<div>
Carbon Nucleophiles ......................................................................... 157</div>
<div>
2.4.2. Reactions of  -Trimethylsilylcarbanions with Carbonyl</div>
<div>
Compounds........................................................................................ 171</div>
<div>
2.4.3. The Julia Olefination Reaction ......................................................... 174</div>
<div>
2.5. Reactions Proceeding by Addition-Cyclization ........................................... 177</div>
<div>
2.5.1. Sulfur Ylides and Related Nucleophiles........................................... 177</div>
<div>
2.5.2. Nucleophilic Addition-Cyclization of  -Haloesters......................... 182</div>
<div>
2.6. Conjugate Addition by Carbon Nucleophiles .............................................. 183</div>
<div>
2.6.1. Conjugate Addition of Enolates........................................................ 183</div>
<div>
2.6.2. Conjugate Addition with Tandem Alkylation .................................. 189</div>
<div>
2.6.3. Conjugate Addition by Enolate Equivalents..................................... 190</div>
<div>
2.6.4. Control of Facial Selectivity in Conjugate</div>
<div>
Addition Reactions ............................................................................ 193</div>
<div>
2.6.5. Conjugate Addition of Organometallic Reagents............................. 197</div>
<div>
2.6.6. Conjugate Addition of Cyanide Ion.................................................. 198</div>
<div>
General References............................................................................................... 200</div>
<div>
Problems ............................................................................................................... 200</div>
<div>
Chapter 3. Functional Group Interconversion</div>
<div>
by Substitution, Including Protection and Deprotection . . . . . . 215</div>
<div>
Introduction........................................................................................................... 215</div>
<div>
3.1. Conversion of Alcohols to Alkylating Agents............................................. 216</div>
<div>
3.1.1. Sulfonate Esters ................................................................................. 216</div>
<div>
3.1.2. Halides ............................................................................................... 217</div>
</div>
<div>
<div>
3.2. Introduction of Functional Groups by Nucleophilic Substitution</div>
<div>
at Saturated Carbon ...................................................................................... 223</div>
<div>
3.2.1. General Solvent Effects..................................................................... 224</div>
<div>
3.2.2. Nitriles ............................................................................................... 225</div>
<div>
3.2.3. Oxygen Nucleophiles ........................................................................ 226</div>
<div>
3.2.4. Nitrogen Nucleophiles....................................................................... 229</div>
<div>
3.2.5. Sulfur Nucleophiles ........................................................................... 233</div>
<div>
3.2.6. Phosphorus Nucleophiles .................................................................. 233</div>
<div>
3.2.7. Summary of Nucleophilic Substitution at Saturated Carbon ........... 234</div>
<div>
3.3. Cleavage of Carbon-Oxygen Bonds in Ethers and Esters........................... 238</div>
<div>
3.4. Interconversion of Carboxylic Acid Derivatives ......................................... 242</div>
<div>
3.4.1. Acylation of Alcohols ....................................................................... 243</div>
<div>
3.4.2. Fischer Esterification......................................................................... 252</div>
<div>
3.4.3. Preparation of Amides....................................................................... 252</div>
<div>
3.5. Installation and Removal of Protective Groups........................................... 258</div>
<div>
3.5.1. Hydroxy-Protecting Groups .............................................................. 258</div>
<div>
3.5.2. Amino-Protecting Groups ................................................................. 267</div>
<div>
3.5.3. Carbonyl-Protecting Groups.............................................................. 272</div>
<div>
3.5.4. Carboxylic Acid–Protecting Groups ................................................. 275</div>
<div>
Problems ............................................................................................................... 277</div>
<div>
Chapter 4. Electrophilic Additions to Carbon-Carbon Multiple Bonds . . . 289</div>
<div>
Introduction........................................................................................................... 289</div>
<div>
4.1. Electrophilic Addition to Alkenes................................................................ 290</div>
<div>
4.1.1. Addition of Hydrogen Halides.......................................................... 290</div>
<div>
4.1.2. Hydration and Other Acid-Catalyzed Additions of Oxygen</div>
<div>
Nucleophiles ...................................................................................... 293</div>
<div>
4.1.3. Oxymercuration-Reduction ............................................................... 294</div>
<div>
4.1.4. Addition of Halogens to Alkenes ..................................................... 298</div>
<div>
4.1.5. Addition of Other Electrophilic Reagents ........................................ 305</div>
<div>
4.1.6. Addition Reactions with Electrophilic Sulfur and Selenium</div>
<div>
Reagents............................................................................................. 307</div>
<div>
4.2. Electrophilic Cyclization .............................................................................. 310</div>
<div>
4.2.1. Halocyclization .................................................................................. 311</div>
<div>
4.2.2. Sulfenylcyclization and Selenenylcyclization................................... 320</div>
<div>
4.2.3. Cyclization by Mercuric Ion ............................................................. 324</div>
<div>
4.3. Electrophilic Substitution <span class="Apple-tab-span" style="white-space: pre;"> </span> to Carbonyl Groups........................................ 328</div>
<div>
4.3.1. Halogenation <span class="Apple-tab-span" style="white-space: pre;"> </span> to Carbonyl Groups ................................................ 328</div>
<div>
4.3.2. Sulfenylation and Selenenylation <span class="Apple-tab-span" style="white-space: pre;"> </span> to Carbonyl Groups ................ 331</div>
<div>
4.4. Additions to Allenes and Alkynes ............................................................... 333</div>
<div>
4.5. Addition at Double Bonds via Organoborane Intermediates ...................... 337</div>
<div>
4.5.1. Hydroboration.................................................................................... 337</div>
<div>
4.5.2. Reactions of Organoboranes ............................................................. 344</div>
<div>
4.5.3. Enantioselective Hydroboration ........................................................ 347</div>
<div>
4.5.4. Hydroboration of Alkynes................................................................. 352</div>
<div>
4.6. Hydroalumination, Carboalumination, Hydrozirconation,</div>
<div>
and Related Reactions .................................................................................. 353</div>
</div>
<div>
<div>
Chapter 5. Reduction of Carbon-Carbon Multiple Bonds, Carbonyl</div>
<div>
Groups, and Other Functional Groups . . . . . . . . . . . . . . . . . . . . . . 367</div>
<div>
Introduction........................................................................................................... 367</div>
<div>
5.1. Addition of Hydrogen at Carbon-Carbon Multiple Bonds.......................... 368</div>
<div>
5.1.1. Hydrogenation Using Heterogeneous Catalysts ............................... 368</div>
<div>
5.1.2. Hydrogenation Using Homogeneous Catalysts ................................ 374</div>
<div>
5.1.3. Enantioselective Hydrogenation........................................................ 376</div>
<div>
5.1.4. Partial Reduction of Alkynes ............................................................ 387</div>
<div>
5.1.5. Hydrogen Transfer from Diimide ..................................................... 388</div>
<div>
5.2. Catalytic Hydrogenation of Carbonyl and Other Functional Groups ......... 390</div>
<div>
5.3. Group III Hydride-Donor Reagents ............................................................. 396</div>
<div>
5.3.1. Comparative Reactivity of Common Hydride</div>
<div>
Donor Reagents ................................................................................. 396</div>
<div>
5.3.2. Stereoselectivity of Hydride Reduction ............................................ 407</div>
<div>
5.3.3. Enantioselective Reduction of Carbonyl Compounds...................... 415</div>
<div>
5.3.4. Reduction of Other Functional Groups by Hydride Donors............ 422</div>
<div>
5.4. Group IV Hydride Donors ........................................................................... 425</div>
<div>
5.4.1. Reactions Involving Silicon Hydrides .............................................. 425</div>
<div>
5.4.2. Hydride Transfer from Carbon ......................................................... 429</div>
<div>
5.5. Reduction Reactions Involving Hydrogen Atom Donors............................ 431</div>
<div>
5.6. Dissolving-Metal Reductions ....................................................................... 434</div>
<div>
5.6.1. Addition of Hydrogen ....................................................................... 435</div>
<div>
5.6.2. Reductive Removal of Functional Groups ....................................... 439</div>
<div>
5.6.3. Reductive Coupling of Carbonyl Compounds.................................. 444</div>
<div>
5.7. Reductive Deoxygenation of Carbonyl Groups........................................... 452</div>
<div>
5.7.1. Reductive Deoxygenation of Carbonyl Groups to Methylene ......... 452</div>
<div>
5.7.2. Reduction of Carbonyl Compounds to Alkenes............................... 454</div>
<div>
5.8. Reductive Elimination and Fragmentation................................................... 457</div>
<div>
Problems ............................................................................................................... 462</div>
<div>
Chapter 6. Concerted Cycloadditions, Unimolecular Rearrangements,</div>
<div>
and Thermal Eliminations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 473</div>
<div>
Introduction........................................................................................................... 473</div>
<div>
6.1. Diels-Alder Reactions................................................................................... 474</div>
<div>
6.1.1. The Diels-Alder Reaction: General Features.................................... 474</div>
<div>
6.1.2. Substituent Effects on the Diels-Alder Reaction.............................. 475</div>
<div>
6.1.3. Lewis Acid Catalysis of the Diels-Alder Reaction .......................... 481</div>
<div>
6.1.4. The Scope and Synthetic Applications</div>
<div>
of the Diels-Alder Reaction .............................................................. 487</div>
<div>
6.1.5. Diastereoselective Diels-Alder Reactions</div>
<div>
Using Chiral Auxiliaries ................................................................... 499</div>
<div>
6.1.6. Enantioselective Catalysts for Diels-Alder Reactions...................... 505</div>
<div>
6.1.7. Intramolecular Diels-Alder Reactions............................................... 518</div>
</div>
<div>
<div>
6.2. 1,3-Dipolar Cycloaddition Reactions ........................................................... 526</div>
<div>
6.2.1. Regioselectivity and Stereochemistry ............................................... 528</div>
<div>
6.2.2. Synthetic Applications of Dipolar Cycloadditions ........................... 531</div>
<div>
6.2.3. Catalysis of 1,3-Dipolar Cycloaddition Reactions ........................... 535</div>
<div>
6.3. [2 + 2] Cycloadditions and Related Reactions Leading</div>
<div>
to Cyclobutanes ............................................................................................ 538</div>
<div>
6.3.1. Cycloaddition Reactions of Ketenes and Alkenes............................ 539</div>
<div>
6.3.2. Photochemical Cycloaddition Reactions........................................... 544</div>
<div>
6.4. [3,3]-Sigmatropic Rearrangements............................................................... 552</div>
<div>
6.4.1. Cope Rearrangements........................................................................ 552</div>
<div>
6.4.2. Claisen and Modified Claisen Rearrangements................................ 560</div>
<div>
6.5. [2,3]-Sigmatropic Rearrangements............................................................... 581</div>
<div>
6.5.1. Rearrangement of Allylic Sulfoxides, Selenoxides,</div>
<div>
and Amine Oxides............................................................................. 581</div>
<div>
6.5.2. Rearrangement of Allylic Sulfonium and Ammonium Ylides......... 583</div>
<div>
6.5.3. Anionic Wittig and Aza-Wittig Rearrangements ............................. 587</div>
<div>
6.6. Unimolecular Thermal Elimination Reactions............................................. 590</div>
<div>
6.6.1. Cheletropic Elimination..................................................................... 591</div>
<div>
6.6.2. Decomposition of Cyclic Azo Compounds ...................................... 593</div>
<div>
6.6.3.  -Eliminations Involving Cyclic Transition Structures.................... 596</div>
<div>
Problems ............................................................................................................... 604</div>
<div>
Chapter 7. Organometallic Compounds of Group I and II Metals . . . . . . . 619</div>
<div>
Introduction........................................................................................................... 619</div>
<div>
7.1. Preparation and Properties of Organomagnesium</div>
<div>
and Organolithium Reagents ........................................................................ 620</div>
<div>
7.1.1. Preparation and Properties of Organomagnesium Reagents ............ 620</div>
<div>
7.1.2. Preparation and Properties of Organolithium Compounds .............. 624</div>
<div>
7.2. Reactions of Organomagnesium and Organolithium Compounds .............. 634</div>
<div>
7.2.1. Reactions with Alkylating Agents .................................................... 634</div>
<div>
7.2.2. Reactions with Carbonyl Compounds .............................................. 637</div>
<div>
7.3. Organometallic Compounds of Group IIB and IIIB Metals ....................... 650</div>
<div>
7.3.1. Organozinc Compounds .................................................................... 650</div>
<div>
7.3.2. Organocadmium Compounds............................................................ 661</div>
<div>
7.3.3. Organomercury Compounds ............................................................. 662</div>
<div>
7.3.4. Organoindium Reagents .................................................................... 663</div>
<div>
7.4. Organolanthanide Reagents.......................................................................... 664</div>
<div>
General References............................................................................................... 666</div>
<div>
Problems ............................................................................................................... 667</div>
<div>
Chapter 8. Reactions Involving Transition Metals. . . . . . . . . . . . . . . . . . . . . . . 675</div>
<div>
Introduction........................................................................................................... 675</div>
<div>
8.1. Organocopper Intermediates......................................................................... 675</div>
<div>
8.1.1. Preparation and Structure of Organocopper Reagents ..................... 675</div>
<div>
8.1.2. Reactions Involving Organocopper Reagents</div>
<div>
and Intermediates............................................................................... 680</div>
</div>
<div>
<div>
8.2. Reactions Involving Organopalladium Intermediates.................................. 706</div>
<div>
8.2.1. Palladium-Catalyzed Nucleophilic Addition</div>
<div>
and Substitution ................................................................................. 709</div>
<div>
8.2.2. The Heck Reaction............................................................................ 715</div>
<div>
8.2.3. Palladium-Catalyzed Cross Coupling ............................................... 723</div>
<div>
8.2.4. Carbonylation Reactions ................................................................... 748</div>
<div>
8.3. Reactions Involving Other Transition Metals.............................................. 754</div>
<div>
8.3.1. Organonickel Compounds................................................................. 754</div>
<div>
8.3.2. Reactions Involving Rhodium and Cobalt........................................ 759</div>
<div>
8.4. The Olefin Metathesis Reaction................................................................... 761</div>
<div>
8.5. Organometallic Compounds with </div>
<div>
-Bonding.............................................. 767</div>
<div>
General References............................................................................................... 771</div>
<div>
Problems ............................................................................................................... 771</div>
<div>
Chapter 9. Carbon-Carbon Bond-Forming Reactions</div>
<div>
of Compounds of Boron, Silicon, and Tin. . . . . . . . . . . . . . . . . . . . 783</div>
<div>
Introduction........................................................................................................... 783</div>
<div>
9.1. Organoboron Compounds............................................................................. 784</div>
<div>
9.1.1. <b>Synthesis </b>of Organoboranes.............................................................. 784</div>
<div>
9.1.2. Carbonylation and Other One-Carbon</div>
<div>
Homologation Reactions ................................................................... 786</div>
<div>
9.1.3. Homologation via <span class="Apple-tab-span" style="white-space: pre;"> </span>-Halo Enolates .................................................. 792</div>
<div>
9.1.4. Stereoselective Alkene Synthesis...................................................... 793</div>
<div>
9.1.5. Nucleophilic Addition of Allylic Groups from</div>
<div>
Boron Compounds............................................................................. 797</div>
<div>
9.2. Organosilicon Compounds ........................................................................... 809</div>
<div>
9.2.1. Synthesis of Organosilanes ............................................................... 809</div>
<div>
9.2.2. General Features of Carbon-Carbon Bond-Forming Reactions</div>
<div>
of Organosilicon Compounds ........................................................... 814</div>
<div>
9.2.3. Additions <b>Reactions </b>with Aldehydes and Ketones .......................... 815</div>
<div>
9.2.4. Reaction with Iminium Ions.............................................................. 825</div>
<div>
9.2.5. Acylation Reactions........................................................................... 826</div>
<div>
9.2.6. Conjugate Addition Reactions .......................................................... 830</div>
<div>
9.3. Organotin Compounds.................................................................................. 833</div>
<div>
9.3.1. Synthesis of Organostannanes........................................................... 833</div>
<div>
9.3.2. Carbon-Carbon Bond-Forming Reactions ........................................ 836</div>
<div>
9.4. Summary of Stereoselectivity Patterns ........................................................ 851</div>
<div>
General References............................................................................................... 852</div>
<div>
Problems ............................................................................................................... 853</div>
<div>
Chapter 10. <b>Reactions </b>Involving Carbocations, Carbenes,</div>
<div>
and Radicals as Reactive Intermediates . . . . . . . . . . . . . . . . . . . . . 861</div>
<div>
Introduction............................................................................................................. 861</div>
<div>
10.1. Reactions and Rearrangement Involving Carbocation Intermediates ......... 862</div>
<div>
10.1.1. Carbon-Carbon Bond Formation Involving Carbocations ............. 862</div>
<div>
10.1.2. Rearrangement of Carbocations ...................................................... 883</div>
<div>
10.1.3. Related Rearrangements.................................................................. 892</div>
<div>
10.1.4. Fragmentation Reactions ................................................................. 897</div>
</div>
<div>
<div>
10.2. Reactions Involving Carbenes and Related Intermediates .......................... 903</div>
<div>
10.2.1. Reactivity of Carbenes .................................................................... 905</div>
<div>
10.2.2. Generation of Carbenes................................................................... 909</div>
<div>
10.2.3. Addition <b>Reactions </b>.......................................................................... 916</div>
<div>
10.2.4. Insertion <b>Reactions </b>.......................................................................... 934</div>
<div>
10.2.5. Generation and Reactions of Ylides</div>
<div>
by Carbenoid Decomposition.......................................................... 938</div>
<div>
10.2.6. Rearrangement Reactions................................................................ 940</div>
<div>
10.2.7. Related <b>Reactions </b>............................................................................ 941</div>
<div>
10.2.8. Nitrenes and Related Intermediates ................................................ 944</div>
<div>
10.2.9. Rearrangements to Electron-Deficient Nitrogen ............................ 947</div>
<div>
10.3. Reactions Involving Free Radical Intermediates ......................................... 956</div>
<div>
10.3.1. Sources of Radical Intermediates.................................................... 957</div>
<div>
10.3.2. Addition Reactions of Radicals with Substituted Alkenes............. 959</div>
<div>
10.3.3. Cyclization of Free Radical Intermediates ..................................... 967</div>
<div>
10.3.4. Additions to C=N Double Bonds................................................... 973</div>
<div>
10.3.5. Tandem Radical Cyclizations and Alkylations............................... 979</div>
<div>
10.3.6. Fragmentation and Rearrangement Reactions ................................ 984</div>
<div>
10.3.7. Intramolecular Functionalization by Radical Reactions................. 989</div>
<div>
Problems ................................................................................................................. 992</div>
<div>
Chapter 11. Aromatic Substitution Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1003</div>
<div>
Introduction............................................................................................................. 1003</div>
<div>
11.1. Electrophilic Aromatic Substitution ............................................................. 1004</div>
<div>
11.1.1. Nitration........................................................................................... 1004</div>
<div>
11.1.2. Halogenation.................................................................................... 1008</div>
<div>
11.1.3. Friedel-Crafts Alkylation................................................................. 1014</div>
<div>
11.1.4. Friedel-Crafts Acylation.................................................................. 1017</div>
<div>
11.1.5. Related Alkylation and Acylation Reactions.................................. 1023</div>
<div>
11.1.6. Electrophilic Metallation ................................................................. 1026</div>
<div>
11.2. Nucleophilic Aromatic Substitution ............................................................. 1027</div>
<div>
11.2.1. Aryl Diazonium Ions as Synthetic Intermediates........................... 1027</div>
<div>
11.2.2. Substitution by the Addition-Elimination Mechanism................... 1035</div>
<div>
11.2.3. Substitution by the Elimination-Addition Mechanism................... 1039</div>
<div>
11.3. Transition Metal–Catalyzed Aromatic Substitution Reactions.................... 1042</div>
<div>
11.3.1. Copper-Catalyzed Reactions ........................................................... 1042</div>
<div>
11.3.2. Palladium-Catalyzed Reactions....................................................... 1045</div>
<div>
11.4. Aromatic Substitution Reactions Involving Radical Intermediates............. 1052</div>
<div>
11.4.1. Aromatic Radical Substitution ........................................................ 1052</div>
<div>
11.4.2. Substitution by the SRN 1 Mechanism ............................................. 1053</div>
<div>
Problems ................................................................................................................. 1056</div>
<div>
Chapter 12. Oxidations. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1063</div>
<div>
Introduction............................................................................................................. 1063</div>
<div>
12.1. Oxidation of Alcohols to Aldehydes, Ketones, or Carboxylic Acids ......... 1063</div>
<div>
12.1.1. Transition Metal Oxidants............................................................... 1063</div>
<div>
12.1.2. Other Oxidants................................................................................. 1070</div>
<div>
<br /></div>
<div>
Contents</div>
<div>
12.2. Addition of Oxygen at Carbon-Carbon Double Bonds ............................... 1074</div>
<div>
12.2.1. Transition Metal Oxidants............................................................... 1074</div>
<div>
12.2.2. Epoxides from Alkenes and Peroxidic Reagents............................ 1091</div>
<div>
12.2.3. Subsequent Transformations of Epoxides ...................................... 1104</div>
<div>
12.3. Allylic Oxidation .......................................................................................... 1116</div>
<div>
12.3.1. Transition Metal Oxidants............................................................... 1116</div>
<div>
12.3.2. Reaction of Alkenes with Singlet Oxygen ..................................... 1117</div>
<div>
12.3.3. Other Oxidants................................................................................. 1124</div>
<div>
12.4. Oxidative Cleavage of Carbon-Carbon Double Bonds ............................... 1126</div>
<div>
12.4.1. Transition Metal Oxidants............................................................... 1126</div>
<div>
12.4.2. Ozonolysis ....................................................................................... 1129</div>
<div>
12.5. Oxidation of Ketones and Aldehydes .......................................................... 1131</div>
<div>
12.5.1. Transition Metal Oxidants............................................................... 1131</div>
<div>
12.5.2. Oxidation of Ketones and Aldehydes by Oxygen</div>
<div>
and Peroxidic Compounds .............................................................. 1134</div>
<div>
12.5.3. Oxidation with Other Reagents....................................................... 1143</div>
<div>
12.6. Selective Oxidative Cleavages at Functional Groups.................................. 1144</div>
<div>
12.6.1. Cleavage of Glycols ........................................................................ 1144</div>
<div>
12.6.2. Oxidative Decarboxylation.............................................................. 1145</div>
<div>
12.7. Oxidations at Unfunctionalized Carbon....................................................... 1148</div>
<div>
Problems ................................................................................................................. 1151</div>
<div>
Chapter 13. Multistep Syntheses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1163</div>
<div>
Introduction............................................................................................................. 1163</div>
<div>
13.1. <b>Synthetic Analysis</b> and Planning.................................................................. 1164</div>
<div>
13.1.1. Retrosynthetic Analysis................................................................... 1164</div>
<div>
13.1.2. Synthetic Equivalent Groups........................................................... 1166</div>
<div>
13.1.3. Control of <b>Stereochemistry </b>............................................................. 1171</div>
<div>
13.2. Illustrative <b>Syntheses</b>.................................................................................... 1173</div>
<div>
13.2.1. Juvabione ......................................................................................... 1174</div>
<div>
13.2.2. Longifolene...................................................................................... 1186</div>
<div>
13.2.3. Prelog-Djerassi Lactone .................................................................. 1196</div>
<div>
13.2.4. Baccatin III and Taxol .................................................................... 1210</div>
<div>
13.2.5. Epothilone A.................................................................................... 1220</div>
<div>
13.2.6. Discodermolide................................................................................ 1231</div>
<div>
13.3. Solid Phase <b>Synthesis</b>................................................................................... 1245</div>
<div>
13.3.1. Solid Phase Polypeptide <b>Synthesis </b>................................................. 1245</div>
<div>
13.3.2. Solid Phase <b>Synthesis </b>of Oligonucleotides..................................... 1250</div>
<div>
13.4. Combinatorial <b>Synthesis</b>............................................................................... 1252</div>
<div>
General References................................................................................................. 1259</div>
<div>
Problems ................................................................................................................. 1260</div>
</div>
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Writing Reaction Mechanisms in Organic Chemistry

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The Art of Writing Reasonable Organic Reaction Mechanisms

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Reaction Mechanisms in Organic Synthesis free books

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<span style="color: red; font-size: large;">Reaction Mechanisms in Organic Synthesis -Free chemistry books Wiley-Blackwell</span></h3>
<b>Organic chemistry</b> is a core part of the <b>chemistry </b>curricula, and advanced levels texts often obscure the essential framework underlying and uniting the vast numbers of reactions as a result of the high level of detail presented. The material in this <b>book </b>is condensed into a manageable text of 350 pages and presented in a clear and logical fashion, focusing purely on the basics of the subject without going through exhaustive detail or repetitive examples. The <b>book </b>aims to bridge the gap between undergraduate organic chemistry textbooks and advanced level textbooks, beginning with a basic introductory course and arranging the reaction mechanisms according to an ascending order of difficulty. As such, the author believes the book will be excellent primer for advanced postgraduates<br />
<br />
<b>Reaction Mechanisms in Organic Synthesis</b> is written from the point of view of the <b>synthetic organic chemist</b>, enabling students and researchers to understand and expand on reactions covered in foundation courses, and to apply them in a practical context by designing <b>syntheses</b>. As a further aid to the practical research student, the content is organized according to the conditions under which a reaction is executed rather than by the types of <b>mechanisms</b>. Particular emphasis is placed on controlling stereospecificity and regiospecificity.<br />
<br />
Topics covered include:<br />
<br />
Transition metal mediated carbon-carbon bond formation reactions<br />
Use of stabilized carbanions, ylides and enamines for carbon-carbon bond formation reactions,<br />
Advanced level use of oxidation and reduction reagents in synthesis.<br />
As a modern text, this book stands out from its competitors due to its comprehensive coverage of recently published research. The book contains specific examples from the latest literature, covering modern reactions and the latest procedural modifications. The focus on contemporary and synthetically useful reactions ensures that the contents are specifically relevant and attractive to postgraduate students and industrial organic chemists.<br />
<br />
<span style="font-size: x-large;">Table of Contents</span><br />
<br />
<span style="font-size: large;">About the author</span><br />
Rakesh Kumar Parashar is a Reader at the Chemistry Deparment, Kirori Mal College, University of Delhi, India<br />
<br />
<br />
<ul>
<li>SYNTHETIC STRATEGIES.</li>
<li>REACTIVE INTERMEDIATES.</li>
<li>STABILIZED CARBANIONS, ENAMINES AND YLIDES.</li>
<li>CARBON – CARBON DOUBLE BOND FORMING REACTIONS.</li>
<li>TRANSITION METALS MEDIATED CARBON-CARBON BOND FORMING REACTIONS.</li>
<li>REDUCTIONS.</li>
<li>OXIDATIONS.</li>
<li>PERICYCLIC REACTIONS</li>
</ul>
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