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Advanced organic chemistry : reactions and mechanisms / Bernard Miller

Miller, Bernard.
Material type: materialTypeLabelBook; Format: print Publisher: New Jersey : Prentice Hall , 2004Edition: 2ª ed.Description: 411 p. : il. ; 24 cm.ISBN: 0131219286.Subject(s): Química orgánica
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Enhanced descriptions from Syndetics:

For undergraduate/graduate level courses in organic reactions and mechanisms.

This text discusses important organic reactions and mechanisms not usually covered in depth in Introductory Organic Chemistry courses. By stressing new material, it avoids student's hostility to repeating material previously studied, while still offering the opportunity to review important concepts and principles in novel settings. This is an ideal text for all students who have previously taken a one-year course in Organic Chemistry, as well as serving students who have already had specialized courses in Physical Organic Chemistry, Stereochemistry, Spectroscopy, etc,. and who need additional knowledge about Organic Reactions.

Indice.Bibliografía

Table of contents provided by Syndetics

  • 1 Introduction
  • Mechanisms of Reactions. Electron Delocalization and Resonance
  • 2 Electrocyclic Reactions
  • Introduction
  • Conrotatory and Disrotatory Processes
  • Explanations for the Woodward-Hoffman Rules
  • Electrocyclic Reactions with Odd Numbers of Atoms
  • Photochemical Cyclizations
  • 3 Cycloaddiction and Cycloreversion Reactions
  • Introduction
  • Suprafacial and Antarafacial Addition
  • Selection Rules for Cycloaddition and Cycloreversion Reactions
  • Examples of Thermal Cycloaddition Reactions
  • Photochemical Cycloadditions
  • 4 Sigmatropic Reactions
  • Theory of Sigmatropic Shifts
  • Experimental Observations
  • Sigmatropic Rearrangements of Charged Systems
  • 5 Linear Free-Energy Relationships
  • The Hammett Equation
  • Separation of Polar, Resonance, and Steric Effects
  • 6 Migrations to Electron-Deficient Centers
  • Migrations to Electron-Deficient Carbons
  • The Nature of the Migrating Groups
  • Rearrangements of Carbocations. Long-Distance Migrations
  • Migrations to Nitrogen and Oxygen
  • 7 Neighboring-Group Effects and Nonclassical Cations
  • Substitution with Retention of Configuration
  • Cyclic Halonium Ions
  • Sulfur and Nitrogen Mustards
  • Trans/Cis Rate Ratios. Neighboring Acetoxy Groups
  • Cyclic Phenonium Ions. Double Bonds as Neighboring Groups
  • Cyclopropane Rings as Neighboring Groups
  • Neighboring Alkyl Groups: 2-Norbornyl Cations
  • 8 Rearrangements of Carbanions and Free Radicals
  • Carbanion Rearrangements
  • Rearrangements of Free Radicals
  • 9 Carbenes, Carbenoids, and Nitrenes
  • Introduction
  • Formation of Carbenes and Nitrenes
  • Singlet and Triplet Carbenes. Additions to Double Bonds
  • Insertion Reactions. Rearrangements
  • 10 Six-Membered Heterocyclic Rings
  • Aromatic Heterocyclic Molecules
  • Reactions of Pyridine and Its Analogs
  • Synthesis of Six-Membered Heterocyclic Rings
  • 11 Five-Membered Heterocyclic Rings
  • Introduction
  • Electron Delocalization and Aromaticity
  • Reactions of Five-Membered Heterocyclic Rings
  • Synthesis of Five-Membered Heteroaromatic Rings
  • Index

Excerpt provided by Syndetics

Among the rewards I've reaped for having written, Advanced Organic Chemistry: Reactions and Mechanisms, are the conversations and correspondence I've had with the users (or perhaps just perusers) of this text. I greatly appreciate the contributions from those of you who have taken the time to inform me of misprints in the first edition. (No errors of fact, I'm happy to say.) The publisher and I have tried to correct those errors in later printings. I'm also grateful for your suggestions of additional subjects to incorporate into the second edition. (I appreciate your faith that there would be a second edition.) Several of you were rightfully indignant that I had skipped so briefly over photochemistry, aside from pericylic photochemical reactions. The complaint is a valid one, and I have tried to make up for the earlier lapse by including a chapter on photochemistry in this edition. A smaller number of readers offered a suggestion that I had thought of as well: the great and increasing importance of synthetic reagents incorporating phosphorus and sulfur atoms makes a discussion of the mechanisms by which those reagents act imperative. I have therefore added a chapter on those reactions to the text of this edition. Of course, a principal purpose of a second edition is to bring the subject matter up-to-date. This edition includes material (and many problems) from the literature through the summer of 2002. I can't really claim that our understanding of organic reaction mechanisms has been revolutionized in the past half-decade, but there have been some fascinating examples of applications of known processes. There have been notable advances in some areas, such as the dehydro Diels-Alder reaction and the Bergman and Meyers-Saito reactions, and in perhaps my favorite example (because of its elegant simplicity), Bakke's demonstration, contradicting a century of experience that pyridime can be easily nitrated in high yield and under mild conditions--provided you know how. I am looking forward to hearing from you in regard to this latest version of my text. I can be reached at miller@chem.umass.edu. Bernard Miller Amherst, MA Excerpted from Advanced Organic Chemistry by Bernard Miller All rights reserved by the original copyright owners. Excerpts are provided for display purposes only and may not be reproduced, reprinted or distributed without the written permission of the publisher.

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