This text is specifically designed to help introductory Organic Chemistry students understand the fundamental concepts covered in undergraduate organic chemistry. The purpose of this book is three-fold: to explode the misconceptions and misgivings that are prevalent regarding this vast subject, provide additional insight for students on a number of concepts essential to mastery of organic chemistry, and explore alternative learning strategies to assist the beginning organic chemistry student in applying a specialized problem solving technique which centers on structure, function and a mechanistic approach. Examples of key chemical transformations are dissected and analyzed to assist students in improving their problem-solving skills. Each chapter contains a number of additional problems and the solutions to those problems are provided at the end of each chapter.

Succeeding in Organic Chemistry

A Systematic Problem-Solving Approach to Mastering Structure, Function and MechanismBy Joseph C. Sloop

AuthorHouse

Copyright © 2010 Joseph C. Sloop
All right reserved.
ISBN: 978-1-4520-1737-2

Contents

Chapter 1 - Studying for Success.........................................................1Chapter 2 - Fundamentals.................................................................6Chapter 3 - Drawing Chemical Structures..................................................23Chapter 4 - Stability of Carbon Compounds and Reactive Intermediates.....................31Chapter 5 - Isomerism and Stereochemistry................................................52Chapter 6 - Function of Reagents in Organic Chemistry....................................64Chapter 7 - Step-by-Step: How Reactions Occur............................................68Appendix A - Reducing Agents.............................................................125Appendix B - Oxidizing Agents............................................................128Index of Key Terms.......................................................................132Index of Chemical Species................................................................134

Chapter One

Studying for Success

1.1 Exploding the Myth

A frequent comment heard from beginning organic chemistry students is that "I'll never be able to learn this - there's too much to memorize." At least part of this statement is true - there is too much material to commit to memory. Unfortunately, many students attack organic chemistry this way, that is, they never get past the idea that memorization is the only key to success.

For those who take foreign languages, learning a foreign alphabet, numbers, grammatical rules and certain idiomatic expressions are necessary before being able to speak, read and write in that language with some degree of fluency. Much of this requires memorization. It is the continued use of these components of a language and not the fact that you memorized the rudiments that eventually leads to an understanding of how to put words together in spoken and written forms.

Organic chemistry is similar. It has a unique language students must know. So, some memorization of the lexicon early is critical. Without it, we could never get to the good part of organic chemistry - understanding how and why chemical reactions take place. Once we can speak, read and write of organic chemistry using the accepted terminology, grasping concepts that are based in that common language no longer need be just memorized - they can be understood and applied. It is the continued use of these concepts through a systematic method of working and solving problems in organic chemistry that moves the true student of organic chemistry beyond the memorization mode.

1.2 Being the Student of a Subject

The difference between simply taking a course and being a student of a subject cannot be overstated. Although on the surface these may have similar implications, e.g. grades and movement into more advanced science coursework, the road a student takes to negotiate organic chemistry will be established early. What this means is that someone learning about organic chemistry can either see this fascinating subject as the beginning of a journey to greater understanding or, as is often the case, a means to some end - another block checked on the way to graduation, preparation for postbaccalaureate studies, etc.

The truth is organic chemistry is not like the general chemistry courses that most undergraduates study. Although it is a survey of many topics in this field, it is something more important: it is the gateway and linch pin for other chemical and life science courses a student may study. Without a firm grasp of the concepts in organic chemistry, chemical engineering, biology, biochemistry, toxicology, and other advanced chemistry courses do not make as much sense as they should. Once you understand this external thread of continuity, the reason for learning organic chemistry is obvious.

In addition, an internal thread of continuity runs through organic chemistry. Think of it as a grand, unfinished play - one with many acts and scenes, tied together by the plot. There may be numerous characters, but they propel the play forward within the context of the plot. While organic chemistry contains many subjects, certain fundamental concepts of structure and function, if studied and understood early, will propel you, as a student forward toward better understanding of this subject and enable you to solve the many different types of problems you will encounter.

One last thing. Organic chemistry is, as are all sciences, a snapshot in time. As students, we must realize that new discoveries, investigations and research continually change organic chemistry. The dozens of academic journals devoted to organic chemistry produce upwards of 100,000 pages of new research results annually. This may add to the complexity of it, but it also makes clear the relevance of learning the fundamentals, so that we may apply them to new cases we may learn of later.

1.3 Studying Organic Chemistry

Now that you understand a bit more about why you want to be a student of organic chemistry, what steps can be taken to enable your success? As in every course, success in organic chemistry depends on many factors - but a few bear special discussion. These include:

* knowing and using all available study resources, * creating an effective study environment and * implementing study sessions using a review, read and practice, preview methodology. * Solving problems using a systematic approach.

Let's look at the first of these, the study resources available for your course.

Knowing and Using All Available Resources

o Frame of mind is key. While institutions choose organic chemistry texts and a variety of other resources in print or electronic media to suit the needs of the chemistry curriculum, you bring the most valuable resource to the table - your mindset. As you prepare to study, your frame of mind will determine, in large part, how well you will retain the subject material when studying. Without a positive attitude, the other reference materials will not be of much use.

o Learning is your responsibility. The teacher cannot force you to learn, you control it. How effectively you study and learn is influenced by your external surroundings and internal level of commitment - factors you determine. By the time you take organic chemistry, you have probably developed some sort of study habits, good and bad. In the end, you must be the judge of what works for you, but remain open to the idea that you may have to "unlearn" some poor study habits and replace them with better ones.

o Use your visual resources - text packages, electronic media and modeling kits. The study of organic chemistry is visually oriented. A wide variety of media is available to enhance your learning experience. Only if you explore the options can you decide what will help you the most.

More than twenty undergraduate organic chemistry texts are available and in use today. For the most part, these text packages are more than satisfactory, providing coverage of essential theory, practical reactions and discussions of how key transformations take place. In that the choice of text is made for you, your success begins with getting the most out of it.

Nowadays, many texts offer study...