Organic Chemistry, 3rd Edition by David R. Klein

Book Preface

WHY I WROTE THIS BOOK

Students who perform poorly on organic chemistry exams often report having invested countless hours studying. Why do many students have difficulty preparing themselves for organic chemistry exams? Certainly, there are several contributing factors, including inefficient study habits, but perhaps the most dominant factor is a fundamental disconnect between what students learn in the lecture hall and the tasks expected of them during an exam. To illustrate the disconnect, consider the following analogy.

Imagine that a prestigious university offers a course entitled “Bike-Riding 101.” Throughout the course, physics and engineering professors explain many concepts and principles (for example, how bicycles have been engineered to minimize air resistance). Students invest significant time studying the information that was presented, and on the last day of the course, the final exam consists of riding a bike for a distance of 100 feet. A few students may have innate talents and can accomplish the task without falling. But most students will fall several times, slowly making it to the finish line, bruised and hurt; and many students will not be able to ride for even one second without falling. Why? Because there is a disconnect between what the students learned and what they were expected to do for their exam.

Many years ago, I noticed that a similar disconnect exists in traditional organic chemistry instruction. That is, learning organic
chemistry is much like bicycle riding; just as the students in the bike-riding analogy were expected to ride a bike after attending lectures, it is often expected that organic chemistry students will independently develop the necessary skills for solving problems. While a few students have innate talents and are able to develop the necessary skills independently, most students require guidance. This guidance was not consistently integrated within existing textbooks, prompting me to write the first edition of my textbook, Organic Chemistry. The main goal of my text was to employ a skills-based approach to bridge the gap between theory (concepts) and practice (problem-solving skills). The second edition further supported this goal by introducing hundreds of additional problems based on the chemical literature, thereby exposing students to exciting real-world examples of chemical research being conducted in real laboratories. The phenomenal success of the first two editions has been extremely gratifying because it provided strong evidence that my skills-based approach is indeed effective at bridging the gap described above.

I firmly believe that the scientific discipline of organic chemistry is NOT merely a compilation of principles, but rather, it is a disciplined method of thought and analysis. Students must certainly understand the concepts and principles, but more importantly, students must learn to think like organic chemists . . . that is, they must learn to become proficient at approaching new situations methodically, based on a repertoire of skills. That is the true essence of organic chemistry.

A SKILLS-BASED APPROACH

To address the disconnect in organic chemistry instruction, I have developed a skills-based approach to instruction. The textbook includes all of the concepts typically covered in an organic chemistry textbook, complete with conceptual checkpoints that promote mastery of the concepts, but special emphasis is placed on skills development through SkillBuilders to support these concepts.

Each SkillBuilder contains three parts: Learn the Skill: contains a solved problem that demonstrates a particular skill.

Practice the Skill: includes numerous problems (similar to the solved problem in Learn the Skill) that give students valuable opportunities to practice and master the skill.

Apply the Skill: contains one or two more problems in which the student must apply the skill to solve real-world problems (as reported in the chemical literature). These problems include conceptual, cumulative, and applied problems that encourage students to think outside of the box. Sometimes problems that foreshadow concepts introduced in later chapters are also included. At the end of each SkillBuilder, a Need More Practice? reference suggests end-of-chapter problems that students can work to practice the skill.

This emphasis upon skills development provides students with a greater opportunity to develop proficiency in the key skills necessary to succeed in organic chemistry. Certainly, not all necessary skills can be covered in a textbook. However, there are certain skills that are fundamental to all other skills.

As an example, resonance structures are used repeatedly throughout the course, and students must become masters of resonance structures early in the course. Therefore, a significant portion of Chapter 2 is devoted to pattern-recognition for drawing resonance structures. Rather than just providing a list of rules and then a few follow-up problems, the skills-based approach provides students with a series of skills, each of which must be mastered in sequence. Each skill is reinforced with numerous practice problems. The sequence of skills is designed to foster and develop proficiency in drawing resonance structures.

The skills-based approach to organic chemistry instruction is a unique approach. Certainly, other textbooks contain tips for problem solving, but no other textbook consistently presents skills development as the primary vehicle for instruction.

Brief Contents
1 A Review of General Chemistry: Electrons, Bonds, and Molecular Properties 1
2 Molecular Representations 49
3 Acids and Bases 93
4 Alkanes and Cycloalkanes 132
5 Stereoisomerism 181
6 Chemical Reactivity and Mechanisms 226
7 Alkyl Halides: Nucleophilic Substitution and Elimination Reactions 271
8 Addition Reactions of Alkenes 343
9 Alkynes 400
10 Radical Reactions 435
11 Synthesis 479
12 Alcohols and Phenols 505
13 Ethers and Epoxides; Thiols and Sulfides 556
14 Infrared Spectroscopy and Mass Spectrometry 602
15 Nuclear Magnetic Resonance Spectroscopy 649
16 Conjugated Pi Systems and Pericyclic Reactions 701
17 Aromatic Compounds 751
18 Aromatic Substitution Reactions 790
19 Aldehydes and Ketones 844
20 Carboxylic Acids and Their Derivatives 898
21 Alpha Carbon Chemistry: Enols and Enolates 954
22 Amines 1008
23 Introduction to Organometallic Compounds 1054
24 Carbohydrates 1107
25 Amino Acids, Peptides, and Proteins 1147
26 Lipids 1190
27 Synthetic Polymers 1227