Organic Chemistry An Acid-Base Approach by Michael B.Smith
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Organic Chemistry An Acid-Base Approach by Michael B.Smith

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Author of Organic Chemistry An Acid-Base Approach PDF

Michael B. Smith is a professor of chemistry in the Department of Chemistry at the University of Connecticut at Storrs.

His research interests focus on the identification of bioactive lipids from the dental pathogen Porphyromonas gingivalis, exploration of the use of conducting polymers as a reaction medium for chemical transformations, development of fluorescent probes for the detection of cancerous tumors, and the synthesis of phenanthridine alkaloids.

He is the author of volumes 6–12 of the Compendium of Organic Synthetic Methods and author of the fifth and sixth editions and the upcoming seventh edition of March’s Advanced Organic Chemistry.

He is also the author of the first and second editions and the upcoming third edition of the graduate-level textbook Organic Synthesis, as well as several monographs.

Dr. Smith received his Ph.D. in organic chemistry from Purdue University in 1977, a BS in chemistry from Virginia Polytechnic Institute in 1969, and an AA from Ferrum College in 1967.

Postdoctoral work at the Cancer ResearchInstitute at Arizona State University and at Massachusetts Institute of Technology preceded his appointment at the University of Connecticut.

Organic Chemistry An Acid-Base Approach Contents

  • Chapter 2: Why Is an Acid-Base Theme Important?
  • Chapter 3: Bonding
  • Chapter 4: Alkanes, Isomers, and an Introduction to Nomenclature
  • Chapter 5: Functional Groups
  • Chapter 6: Acids, Bases, Nucleophiles, and Electrophiles
  • Chapter 7: Chemical Reactions, Bond Energy, and Kinetics
  • Chapter 8: Rotamers and Conformation
  • Chapter 9: Stereoisomers: Chirality, Enantiomers, and Diastereomers
  • Chapter 10: Acid-Base Reactions of π-Bonds
  • Chapter 11: Nucleophiles: Lewis Base-Like Reactionsat sp3 Carbon
  •  Chapter 12: Base-Induced Elimination Reactions
  • Chapter 13: Substitution and Elimination Reactions Can Compete
  • Chapter 14: Spectroscopic Methods of Identification
  • Chapter 15: Organometallic Reagents
  • Chapter 16: Carbonyl Compounds: Structure, Nomenclature, Reactivity
  •  Chapter 17: Oxidation
  • Chapter 18: Reactions of Aldehydes and Ketones
  • Chapter 19: Reduction
  • Chapter 20: Carboxylic Acid Derivatives and Acyl Substitution
  • Chapter 21: Aromatic Compounds and Benzene Derivatives
  • Chapter 22: Enolate Anions: Acyl Addition and Acyl Substitution
  • Chapter 23: Difunctional Molecules: Dienes and Conjugated Carbonyl Compounds
  • Chapter 24: Difunctional Molecules: Pericyclic Reaction
  • Chapter 25: Disconnections and Synthesis
  • Chapter 26: Heteroaromatic Compounds
  • Chapter 27: Multifunctional Compounds: Amino Acids and Peptides
  • Chapter 28: Multifunctional Compounds: Carbohydrates

Preface to Organic Chemistry An Acid-Base Approach PDF

Perhaps the most common fable about organic chemistry is the one often heard in the first few days of the course: Organic chemistry is a memorization course. Memorize what you need and regurgitate it on the test and you will pass.

This assessment is wrong on so many levels that it serves as a starting point to describe this book. One reason for the fable is that it may be difficult to ascertain a fundamental theme that ties organic chemistry together.

The other issue is the fact that organic chemistry builds from the first day to the last and is not compartmentalized.

For this reason, a theme is even more important. Is there a common, underlying theme for organic chemistry that allows one to understand it rather than simply memorize it? In this book, acids and bases provide the theme.

It is important to understand the relationships among functional groups. How are they similar and what structural motifs make them react differently? What is the relationship between structure and chemical reactivity?

These questions point to understanding not only the chemical reactions that populate an organic chemistry book, but also the mechanisms used to describe those reactions.

The theme of this book is the premise that many if not most reactions in organic chemistry can be explained by variations of fundamental acid-base chemistry concepts. Moreover, the individual steps in many important mechanisms rely on acid-base reactions.

The ability to see these relationships makes understanding organic chemistry easier and, perhaps more importantly, allows one to make predictions about reactivity when memory fails. Apart from the acid-base theme, this book uses several techniques to assist students in their studies.

A list of concepts that the student should know before reading the chapter is listed at the beginning of virtually every chapter. A list of concepts that should be known after the chapter is completed is also provided at the beginning of most chapters.

Each chapter concludes with this same list of the concepts that should now have been learned, and a correlation of each concept with the homework problems is provided. The intent is to help identify concepts that need to work apart from those that are readily understood.

Each chapter has a number of embedded problems. They will help the student think about the concept and possibly review something from a previous chapter that's pertinent, with the goal of better understanding that section.

The answers to these problems are provided at the end of each chapter. Regular homework problems are given with the intention of offering help in understanding the concepts in the chapter.

For additional material and a solutions manual, please see the book Web site ( Experimental details are provided for key reactions to introduce the reaction.

The point is to show that the experiment shows a result and then we try to understand that result in the context of the structural features of the reactive species. Mechanisms are given as part of the discussion of key reactions.

The mechanism is discussed in most cases first as a walk-through of the reaction to understand how the transformation occurred, and then structures for the walkthrough are provided that constitute the mechanism.

Many of these mechanistic steps will involve acid-base reactions—both Brønsted–Lowry and Lewis. The book begins with an introduction to organic chemistry that describes what it is as well as individuals who have contributed to building organic chemistry as a scientific discipline.

Chapter 2 provides a bridge between the acid-base discussions in a typical general chemistry book and those in this organic chemistry book.

An understanding of bonding is critical to understanding the structure of organic molecules; this is provided in Chapter 3, followed by Chapter 4 with an introduction to alkanes, the basic structure of organic molecules, and the fundamental rules of nomenclature.

Chapter 5 introduces the concept of functional groups as well as several important functional groups that appear in organic molecules.

This chapter includes an extension of the basic nomenclature rules to include functional groups. Chapter 6 returns to the acid-base theme to give a direct correlation between acid-base reactions and organic chemical reactions that involve the functional groups just introduced in Chapter 5.

Chapter 7 extends the acid-base concept of equilibrium reactions to discuss bond energetics and kinetics. Rotation about single covalent bonds leads to different orientations of atoms and groups within a molecule, known as conformations; this is presented in Chapter 8.

Chapter 9 introduces the concept of chirality and the relationship between chirality and structure. Chapter 10 introduces the acid-base chemistry of molecules that contain the C=C and C≡C functional groups.

Related reactions that do not fall under the acid-base category are also presented. Chapter 11 uses nucleophiles, which are loosely categorized as specialized Lewis bases, in reactions with alkyl halides. These are substitution reactions.

Chapter 12 shows the acid-base reaction of alkyl halides that leads to alkenes (an elimination reaction), and Chapter 13 ties Chapters 11 and 12 together with a series of simplifying assumptions that allow one to make predictions concerning the major product.

Chapter 14 introduces the methods used to identify the structure of organic molecules: mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectroscopy.

This chapter is in the middle of the book, but it may be presented in either semester, and homework problems associated with this chapter are incorporated throughout.

All homework problems requiring the information in Chapter 14 are clearly marked and segregated from the other problems. Therefore, this chapter may be introduced in either semester and the associated homework problems can be easily found.

Chapter 15 provides a brief introduction to commonly used organic molecules that also have a carbon-metal bond—organometallics.

Chapter 16 introduces the fundamental characteristics of molecules that contain the carbon functional group, along with a review of the nomenclature of carbonyl-containing molecules.

Carbonyl compounds are often prepared by oxidation reactions, and several key oxidation reactions are discussed in Chapter 17.

Oxidation reactions of a few other functional groups are included. Chapter 18 elaborates on the chemical reactions of the carbonyl-containing molecules known as aldehydes and ketones. This chemistry is dominated by the acyl addition reaction introduced in Chapter 16.

Chapter 19 in effect continues the chemistry of carbonyls by introducing reduction reactions. Carbonyl-containing molecules, as well as molecules that contain other functional groups, may be reduced to different functional groups, and such reactions are discussed in this chapter.

Chapter 20 continues carbonyl chemistry by discussing chemical reactions of the carboxylic acid derivatives introduced in Chapter 16, with a focus on acyl substitution reactions.

Chapter 21 discusses the concept of aromaticity as well as the nomenclature and the specialized chemical reactions of aromatic compounds such as benzene and its derivatives.

This chapter comes late in the book, with the notion that the chemistry of aliphatic compounds is simply used more often.

The acid-base theme is continued with the recognition that the fundamental substitution chemistry associated with benzene derivatives may be explained by the reaction of aromatic rings as Lewis bases or nucleophiles with electrophilic reagents.

The reactions of benzene derivatives with strong bases and good nucleophiles are also presented.

Chapter 22 returns to carbonyl chemistry and a discussion of the acid-base properties of carbonyl compounds.

The proton on the α-carbon (directly attached to the carbonyl) is slightly acidic and removal with a suitable base leads to an enolate anion. Enolate anions react as nucleophiles in aliphatic substitution, acyl addition, and acyl substitution reactions.

Chapter 23 begins a discussion of multifunctional molecules that will conclude the book and, in many courses, may be considered as special topic material, beginning with simple conjugated dienes and conjugated carbonyl compounds.

Ultraviolet spectroscopy is discussed in the context of identifying conjugated compounds.

Chapter 24 continues this discussion with pericyclic reactions that involve dienes and other multifunctional compounds.

Chapter 25 is a stand-alone chapter to introduce the retrosynthetic approach to synthesis. It is presented as part of the discussion on multifunctional molecules, but it may be taught at any point in the course.

As with spectroscopy, synthesis problems are clearly marked homework problems in several chapters and are segregated from the other problems so that they are easily found. The book concludes with three chapters that involve multifunctional molecules.

Heterocycles are introduced in Chapter 26, with nomenclature and structure as well as some elementary chemical reactions of heterocyclic compounds. Amino acids and peptides are discussed in Chapter 27 and carbohydrates and nucleic acids are discussed in Chapter 28.

These last three chapters are, arguably, the most important to biological chemistry. This book constitutes an important introduction to organic chemistry.

The reactions and mechanisms contained herein describe its most fundamental concepts, which are used in industry, biological chemistry and biochemistry, molecular biology, and pharmacy. These concepts constitute the fundamental basis of life processes, which means that they are pertinent to the study of medicine.

For that reason, most chapters end with a brief section that describes biological applications for each concept.

The last two chapters (27 and 28) have more than one section that discusses biological applications because these molecules make up the proteins, enzymes, cellular structure, and DNA and RNA found in living systems.

It is hoped that this course will provide the skills to go to the next level of study using this fundamental understanding of acids and bases applied to organic transformations and organic molecules.

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