## Study Guide and Solutions Manual for Organic Chemistry, Eighth Edition

By Neil E. Schore

**Contents:**

Preface

General Introduction

Chapter 1 Structure and Bonding in Organic Molecules

Solutions to Problems

Chapter 2 Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules

Solutions to Problems

Chapter 3 Reactions of Alkanes: Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity

Solutions to Problems

Chapter 4 Cycloalkanes

Solutions to Problems

Chapter 5 Stereoisomers

Solutions to Problems

Chapter 6 Properties and Reactions of Haloalkanes: Bimolecular Nucleophilic Substitution

Solutions to Problems

Chapter 7 Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

Solutions to Problems

Chapter 8 Hydroxy Functional Group: Alcohols: Properties, Preparation, and Strategy of Synthesis

Solutions to Problems

Chapter 9 Further Reactions of Alcohols and the Chemistry of Ethers

Solutions to Problems

Chapter 10 Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure

Solutions to Problems

Chapter 11 Alkenes; Infrared Spectroscopy and Mass Spectrometry

Solutions to Problems

Chapter 12 Reactions of Alkenes

Solutions to Problems

Chapter 13 Alkynes: The Carbon–Carbon Triple Bond

Solutions to Problems

Chapter 14 Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy

Solutions to Problems

Chapter 15 Benzene and Aromaticity: **Electrophilic Aromatic Substitution**

Solutions to Problems

Chapter 16 Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity

Solutions to Problems

Chapter 17 Aldehydes and Ketones: The Carbonyl Group

Solutions to Problems

Chapter 18 Enols, Enolates, and the Aldol Condensation: α, β-Unsaturated Aldehydes and Ketones

Solutions to Problems

Chapter 19 Carboxylic Acids

Solutions to Problems

Chapter 20 Carboxylic Acid Derivatives

Solutions to Problems

Chapter 21 Amines and Their Derivatives: Functional Groups Containing Nitrogen

Solutions to Problems

Chapter 22 Chemistry of Benzene Substituents: Alkylbenzenes, Phenols, and Anilines

Solutions to Problems

Chapter 23 Ester Enolates and the Claisen Condensation: Synthesis of β-Dicarbonyl Compounds; Acyl Anion Equivalents

Solutions to Problems

Chapter 24 Carbohydrates: Polyfunctional Compounds in Nature

Solutions to Problems

Chapter 25 Heterocycles: Heteroatoms in Cyclic Organic Compounds

Solutions to Problems

Chapter 26 Amino Acids, Peptides, Proteins, and Nucleic Acids: Nitrogen-Containing Polymers in Nature

Solutions to Problems

Glossary

**Preface:**

From One Organic Chemistry Teacher to Another “I study all the time, I understand what you’re saying in the lecture, and I do all the problems. So how come I got a ‘12’ on the exam?” Ouch! We’ve all heard this from our students, haven’t we? (At least I assume I’m not the only one.) Why is it that perfectly reasonable students of perfectly reasonable intelligence sometimes wind up being hopelessly buried by this course? More to the point, what, if anything, can we do about it?

Clearly, in a perfect world, where students have ample time to do everything they’re supposed to do and know everything that they need to know from freshman chemistry, things would be better. Typically, however, that is not the case. Students are pressed to budget their time and divide it among their courses, their jobs, and their lives. Because they often can’t spend sufficient time studying for each course during the term, they sometimes lag so far behind in their studying that, come exam time, they fall into the “Big Trap”: they try to memorize everything. And then they get those “12”s and wonder what went wrong.

Well, we’re the teachers, and we ought to know what’s gone wrong and how to help the students do better. My experience has taught me that two critical factors almost always contribute to these predicaments: flawed understanding of basic concepts and lack of ability to apply the concepts to new, unfamiliar situations. The first involves an unsure grasp of mostly descriptive, informational material. Students must learn this fundamental material as surely as they learn the grammar and vocabulary of a foreign language. The basics can usually be mastered by serious study. Continuing emphasis on concepts and mechanisms, including the self-consistent, functional use of color in the textbook, and reemphasis in terms of relationships among topics in the “Introduction” and “Keys” sections of each chapter of this study guide are intended to make this process as manageable as possible for students.

The second factor is the killer for teachers: how to teach struggling students to (1) sort out the concepts and **patterns** relevant to a given problem and then (2) apply them in a logical way to the development of an answer. We all recognize that what we are trying to teach is not simply a body of information, but a thought process. How does one go about teaching a thought process? I use the “WHIP” strategy to lead students through a problem step-by-step, so they can experience the process, even if initially only from the outside looking in. They must be shown the choices that need to be made, why some are wrong and can be dismissed immediately, and how to evaluate the others. My goal in the preparation of the solutions to the end-of-chapter problems in the text was precisely this: to illustrate the thought process involved in getting from the problem to a reasonable answer. I’ve provided the greatest amount of detail in the earlier chapters, and I’ve deliberately omitted details in answers to some problems toward the end of the book. The learning process almost always requires direct experience on the students’ part. It isn’t enough for students to read an answer even if it is fully understood! Students must have opportunities to carry out the mental process for themselves.

Therefore in many cases I’ve begun an answer with a hint, asking students to go back and attempt the problem again if they had difficulty the first time. Getting started is often the hard part, and this ploy at least gives serious students a second chance to make the connections required to proceed to a solution. It’s a technique I use in helping students during office hours, and it seems to work.

I’ve also tried to be as rigorous and as complete as possible in the presentation of mechanisms, even to the extent of showing two-electron arrows in simple proton transfer processes. This might seem excessive to some, but remember, here we are dealing with students who may be in a position to derive clarifying insight from even the most insignificant of points. In the end, we must face the fact that our job is not really to “teach students organic chemistry.” Our goal really has to be to teach students how to learn what organic chemistry is all about and how it works. Teaching students “how to learn” can be a difficult task. I hope the approach taken in this book is helpful in achieving that end.

Neil E. Schore

Davis, California