Organic Chemistry II For Dummies E-Book

John T. Moore

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 322

Veröffentlichungsjahr: 2010

Beschreibung

A plain-English guide to one of the toughest courses around So, you survived the first semester of Organic Chemistry (maybe even by the skin of your teeth) and now it's time to get back to the classroom and lab! Organic Chemistry II For Dummies is an easy-to-understand reference to this often challenging subject. Thanks to this book, you'll get friendly and comprehensible guidance on everything you can expect to encounter in your Organic Chemistry II course. * An extension of the successful Organic Chemistry I For Dummies * Covers topics in a straightforward and effective manner * Explains concepts and terms in a fast and easy-to-understand way Whether you're confused by composites, baffled by biomolecules, or anything in between, Organic Chemistry II For Dummies gives you the help you need -- in plain English!

Leseprobe

Organic Chemistry II For Dummies®

Table of Contents

Introduction

About This Book

Conventions Used in This Book

What You’re Not to Read

Foolish Assumptions

How This Book Is Organized

Part I: Brushing Up on Important Organic Chemistry I Concepts

Part II: Discovering Aromatic (And Not So Aromatic) Compounds

Part III: Carbonyls: Good Alcohols Gone Bad

Part IV: Advanced Topics (Every Student’s Nightmare)

Part V: Pulling It All Together

Part VI: The Part of Tens

Icons Used in This Book

Where to Go from Here

Part I: Brushing Up on Important Organic Chemistry I Concepts

Chapter 1: Organic Chemistry II: Here We Go Again!

Recapping Organic Chemistry I

Intermolecular forces

Functional groups

Reactions

Spectroscopy

Isomerism and optical activity

Looking Ahead to Organic Chemistry II

Chapter 2: Remembering How We Do It: Mechanisms

Duck — Here Come the Arrows

Coming Around to Curved Arrows

Getting Ready for Some Basic Moves

Bond → lone pair

Bond → bond

Lone pair → bond

Combining the Basic Moves

Intermediates

Keys to substitution and elimination mechanisms

Revisiting Free-Radical Mechanisms

Part II: Discovering Aromatic (And Not So Aromatic) Compounds

Chapter 3: Alcohols and Ethers: Not Just for Drinking and Sleeping

Getting Acquainted with Alcohols

Structure and nomenclature of alcohols

Physical properties of alcohols

Making moonshine: Synthesis of alcohols

What will they do besides burn? Reactions of alcohols

Introducing Ether (Not the Ether Bunny)

Structure and nomenclature of ethers

Sleepy time: Physical properties of ethers

Synthesis of ethers

Reactions of ethers

Summarizing the Spectra of Alcohols and Ethers

Chapter 4: Conjugated Unsaturated Systems

When You Don’t Have Enough: Unsaturated Systems

Conjugated systems

The allylic radical

Butadiene

Delocalization and Resonance

Resonance rules

Stability of conjugated unsaturated systems

Reactions of Conjugated Unsaturated Systems

Put in the second string: Substitution reactions

Electrophilic addition

More than a tree: Diels-Alder reactions

Passing an Exam with Diels-Adler Questions

Indentifying the product

Identifying the reactants

Chapter 5: "Seeing" Molecules: Spectroscopy Revisited

Chemical Fingerprints: Infrared Spectroscopy

Double bonds

Triple bonds

O-H and N-H stretches

C-H stretches

Suntans and Beyond: Ultraviolet and Visible Spectroscopy

Not Weight Watchers, Mass Watchers: Mass Spectroscopy

The molecular ion

Fragmentation

No Glowing Here: NMR Spectroscopy

Proton

Carbon-13

Chapter 6: Introducing Aromatics

Benzene: Where It All Starts

Figuring out benzene’s structure

Understanding benzene’s resonance

The stability of benzene

Physical properties of benzene

Organic math — Hückel’s Rule

Other aromatics

Smelly Relatives: The Aromatic Family

Nomenclature of the aromatic family

Derivatives of benzene

Branches of aromatic groups

Black Sheep of the Family: Heterocyclic Aromatic Compounds

Aromatic nitrogen compounds

Aromatic oxygen and sulfur compounds

Spectroscopy of Aromatic Compounds

IR

UV-vis

NMR

Mass spec

Chapter 7: Aromatic Substitution Part I: Attack of the Electrophiles

Basics of Electrophilic Substitution Reactions

Reactions of Benzene

Halogenation of benzene

Nitration of benzene

Sulfonation of benzene

Friedel-Crafts Reactions

Alkylation

Acylation

Why Do an Alkylation?

Changing Things: Modifying the Reactivity of an Aromatic

Lights, camera, action: Directing

Turning it on, turning it off: Activating and deactivating

Steric hindrance

Limitations of Electrophilic Substitution Reactions

Chapter 8: Aromatic Substitution Part II: Attack of the Nucleophiles and Other Reactions

Coming Back to Nucleophilic Substitution Reactions

Mastering the Mechanisms of Nucleophilic Substitution Reactions

Losing and Gaining: Mechanisms of Elimination/Addition Reactions

Benzyne

The elimination/addition mechanism

Synthetic Strategies for Making Aromatic Compounds

Briefly Exploring Other Reactions

Part III: Carbonyls: Good Alcohols Gone Bad

Chapter 9: Comprehending Carbonyls

Carbonyl Basics

Considering compounds containing the carbonyl group

Getting to know the acidic carbonyl

Polarity of Carbonyls

Resonance in Carbonyls

Reactivity of the Carbonyl Group

Spectroscopy of Carbonyls

Infrared spectroscopy

Ultraviolet-visible (electronic) spectroscopy

Nuclear magnetic resonance (NMR) spectroscopy

Mass spectroscopy

Chapter 10: Aldehydes and Ketones

Meeting Alcohol’s Relatives: Structure and Nomenclature

Defining Physical Properties of Aldehydes and Ketones

Creating Aldehydes and Ketones with Synthesis Reactions

Oxidation reactions

Reduction reactions

Other reactions

Taking Them a Step Further: Reactions of Aldehydes and Ketones

Nucleophilic attack of aldehydes and ketones

Oxidation of aldehydes and ketones

The Baeyer-Villiger reaction

Checking Out Spectroscopy Specs

Chapter 11: Enols and Enolates

Getting to Know Enols and Enolates

Enough already: Structure of enols and enolates

I thought I saw a tautomer

Studying the Synthesis of Enols and Enolates

Thinking Through Reactions of Enols and Enolates

Haloform reactions

Aldol reactions and condensations

Addition reactions to unsaturated aldehydes and ketones

Other enolate-related reactions

Miscellaneous reactions

Chapter 12: Carboxylic Acids and Their Derivatives

Seeing the Structure and Nomenclature of Carboxylic Acids and Derivatives

Structure

Nomenclature

Checking Out Some Physical Properties of Carboxylic Acids and Derivatives

Carboxylic acids

Esters

Amides

Considering the Acidity of Carboxylic Acids

Determining How Carboxylic Acids and Derivatives Are Synthesized

Synthesizing carboxylic acids

Developing acyl halides with halogen

Removing water to form acid anhydrides

Uniting acids and alcohols to make esters

Bringing acids and bases together to create amides

Exploring Reactions

Generous carboxylic acids

Simple acyl halide and anhydride reactions

Hydrolysis of esters

Amide reactions, ester’s cousins

Other reactions of carboxylic acids and derivatives

Taking a Look at Spectroscopy and Chemical Tests

Identifying compounds with spectral data

Using chemical tests

Part IV: Advanced Topics (Every Student’s Nightmare)

Chapter 13: Amines and Friends

Breaking Down the Structure and Nomenclature of Nitrogen Compounds

Primary amines

Secondary and tertiary amines

Quaternary amines (quaternary ammonium salts)

Heterocyclics

Sizing Up the Physical Properties

Understanding the Basicity of Nitrogen Compounds

Synthesizing Nitrogen Compounds

Nucleophilic substitution reactions

Reduction preparations

Seeing How Nitrogen Compounds React

Reactions with nitrous acid

Replacement reactions

Coupling reactions of diazonium salts

Reactions with sulfonyl chlorides

Exploring elimination reactions

Mastering Multistep Synthesis

Identifying Nitrogen Compounds with Analysis and Spectroscopy

Chapter 14: Metals Muscling In: Organometallics

Grignard Reagents: Grin and Bear It

Preparation of Grignard reagents

Reactions of Grignard reagents

Organolithium Reagents

Formation of Other Organometallics

Putting It Together

Chapter 15: More Reactions of Carbonyl Compounds

Checking Out the Claisen Condensation and Its Variations

Doing the two-step: Claisen condensation

Circling around: Dieckmann condensation

Doubling Up: Crossed Claisen condensation

Other carbanions

Exploring Acetoacetic Ester Synthesis

Defining Malonic Ester Synthesis

Working with Other Active Hydrogen Atoms

Reacting with Knoevenagel Condensation

Looking at Mannich Reactions

Creating Enamines: Stork Enamine Synthesis

Putting It All Together with Barbiturates

Chapter 16: Living Large: Biomolecules

Delving into Carbohydrate Complexities

Introducing carbohydrates

Examining the many reactions of monosaccharides

Synthesizing and degrading monosaccharides

Meeting the (D-)aldose family

Checking out a few disaccharides

Looking at some polysaccharides

Discovering nitrogen-containing sugars

Lipids: Storing Energy Now So You Can Study Longer Later

Pondering the properties of fats

Soaping up with saponification

Bulking Up on Amino Acids and Proteins

Introducing amino acids

Perusing the physical properties of amino acids

Studying the synthesis of amino acids

Part V: Pulling It All Together

Chapter 17: Overview of Synthesis Strategies

Working with One-Step Synthesis

Tackling Multistep Synthesis

Practicing Retrosynthetic and Synthetic Analysis

Example 1

Example 2

Example 3

Example 4

Example 5

Chapter 18: Roadmaps and Predicting Products

Preparing with Roadmap Basics

Practicing Roadmap Problems

Problem one

Solution one

Problem two

Solution two

Problem three

Solution three

Predicting Products

Part VI: The Part of Tens

Chapter 19: Ten Surefire Ways to Fail Organic Chemistry II

Simply Read and Memorize Concepts

Don’t Bother Working the Homework Problems and Exercises

Don’t Buy a Model Kit

Don’t Worry About Falling Behind

Don’t Bother Learning Reactions

If Your Textbook Confuses You, Don’t Bother with Additional Resources

Don’t Bother Reading the Chapter before Attending Class

Attend Class Only When You Feel Like It

Don’t Bother Taking Notes — Just Listen (When You Aren’t Sleeping or Texting)

Don’t Bother Asking Questions

Chapter 20: More than Ten Ways to Increase Your Score on an Organic Chemistry Exam

Don’t Cram the Night before a Test

Try Doing the Problem Sets and Practice Tests Twice

Study the Mistakes You Made on Previous Exams

Know Precisely Where, Why, and How the Electrons Are Moving

Relax and Get Enough Sleep before the Exam

Think Before You Write

Include Formal Charges in Your Structures When Appropriate

Check That You Haven’t Lost Any Carbon Atoms

Include E/Z, R/S, cis/trans Prefixes in Naming Organic Structures

Think of Spectroscopy, Especially NMR, As a Puzzle

Make Sure That Each Carbon Atom Has Four Bonds

Appendix: Named Reactions

Organic Chemistry II For Dummies®

by John T. Moore, EdD, and Richard H. Langley, PhD

Organic Chemistry II For Dummies®

Published byWiley Publishing, Inc.111 River St.Hoboken, NJ 07030-5774www.wiley.com

Copyright © 2010 by Wiley Publishing, Inc., Indianapolis, Indiana

Published simultaneously in Canada

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About the Authors

John T. Moore, EdD, grew up in the foothills of western North Carolina. He attended the University of North Carolina–Asheville where he received his bachelor’s degree in chemistry. He earned his master’s degree in chemistry from Furman University in Greenville, South Carolina. After a stint in the United States Army, he decided to try his hand at teaching. In 1971 he joined the chemistry faculty of Stephen F. Austin State University in Nacogdoches, Texas, where he still teaches chemistry. In 1985 he went back to school part time and in 1991 received his doctorate in education from Texas A&M University. For the past several years he has been the co-editor (along with one of his former students) of the “Chemistry for Kids” feature of The Journal of Chemical Education. In 2003 his first book, Chemistry For Dummies, was published by Wiley, soon to be followed by Chemistry Made Simple (Broadway) and Chemistry Essentials For Dummies (Wiley). John enjoys cooking and making custom knife handles from exotic woods.

Richard H. Langley, PhD, grew up in southwestern Ohio. He attended Miami University in Oxford, Ohio, where he received bachelor’s degrees in chemistry and in mineralogy and a master’s degree in chemistry. His next stop was the University of Nebraska in Lincoln, Nebraska, where he received his doctorate in chemistry. Afterwards he took a postdoctoral position at Arizona State University in Tempe, Arizona, followed by a visiting assistant professor position at the University of Wisconsin–River Falls. In 1982 he moved to Stephen F. Austin State University. For the past several years he and John have been graders for the free-response portion of the AP Chemistry Exam. He and John have collaborated on several writing projects, including 5 Steps to a Five AP Chemistry and Chemistry for the Utterly Confused (both published by McGraw-Hill). Rich enjoys jewelry making and science fiction.

Dedication

John: I dedicate this book to my wife, Robin; sons, Matthew and Jason; my wonderful daughter-in-law, Sara; and the two most wonderful grandkids in the world, Zane and Sadie. I love you guys.

Rich: I dedicate this book to my mother.

Authors’ Acknowledgments

We would not have had the opportunity to write this book without the encouragement of our agent Grace Freedson. We would also like to thank Chrissy Guthrie for her support and assistance in the early portion of this project and to Sarah Faulkner who helped us complete it. We would also like to thank our copy editor, Caitie Copple, and our technical editors, Susan Klein and Joe Burnell.

Many thanks to our colleagues Russell Franks and Jim Garrett who helped with suggestions and ideas. Rich would also like to acknowledge Danica Dizon for her suggestions, ideas, and inspiration. Thanks to all of the people at Wiley publishing who help bring this project from concept to publication.

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Introduction

Welcome to Organic Chemistry II For Dummies. We’re certainly happy you decided to delve further into the fascinating world of organic chemistry. It’s a complex area of chemistry, but understanding organic chemistry isn’t really that difficult. It simply takes hard work, attention to detail, some imagination, and the desire to know. Organic chemistry, like any area of chemistry, is not a spectator sport. You need to interact with the material, try different study techniques, and ask yourself why things happen the way they do.

Organic Chemistry II is a more intricate course than the typical freshman introductory chemistry course, and you may find that it’s also more involved than Organic I. You may actually need to use those things you learned (and study habits you developed) in Organic I to be successful in Organic II. But if you work hard, you can get through your Organic II course. More importantly, you may grow to appreciate the myriad chemical reactions that take place in the diverse world of organic chemistry.

About This Book

Organic Chemistry II For Dummies is an overview of the material covered in the second half of a typical college-level organic chemistry course. We have made every attempt to keep the material as current as possible, but the field of chemistry is changing ever so quickly as new reactions are developed and the fields of biochemistry and biotechnology inspire new avenues of research. The basics, however, stay the same, and they are where we concentrate our attention.

As you flip through this book, you see a lot of chemical structures and reactions. Much of organic chemistry involves knowing the structures of the molecules involved in organic reactions. If you’re in an Organic Chemistry II course, you made it through the first semester of organic chemistry, so you recognize many of the structures, or at least the functional groups, from your previous semester’s study.

If you bought this book just to gain general knowledge about a fascinating subject, try not to get bogged down in the details. Skim the chapters. If you find a topic that interests you, stop and dive in. Have fun learning something new.

If you’re taking an organic chemistry course, you can use this rather inexpensive book to supplement that very expensive organic textbook.

Conventions Used in This Book

We have organized this book in a logical progression of topics; your second semester organic chemistry course may progress similarly. In addition, we set up the following conventions to make navigating this book easier:

Italicsintroduce new terms that you need to know.

Bold text highlights keywords within a bulleted list.

We make extensive use of illustrations of structures and reactions. While reading, try to follow along in the associated figures, whether they be structures or reactions.

What You’re Not to Read

You don’t have a whole lot of money invested in this book, so don’t feel obliged to read what you don’t need. Concentrate on the topic(s) in which you need help. Feel free to skip over any text in a gray shaded box (which we refer to as sidebars). Although interesting, they aren’t required reading.

Foolish Assumptions

We assume — and we all know about the perils of assumptions — that you are one of the following:

A student taking a college-level organic chemistry course.

A student reviewing organic chemistry for some type of standardized exam (the MCAT, for example).

An individual who just wants to know something about organic chemistry.

If you fall into a different category, you’re special and we hope you enjoy this book anyway.

How This Book Is Organized

The topics in this book are divided into six parts. Use the following descriptions and the table of contents to map out your strategy of study.

Part I: Brushing Up on Important Organic Chemistry I Concepts

Part I is really a rapid review of many of the concepts found in an Organic Chemistry I course. It’s designed to review the topics that you need in Organic II. We set the stage by giving you an overview of Organic Chemistry II, and then review mechanisms. Next we cover alcohols and ethers, their properties, synthesis, and reactions; followed by an overview of conjugated unsaturated systems. We end this review section with a discussion of spectroscopy, including IR, UV-visible, mass spec, and, of course, NMR. A whirlwind tour of Organic I!

Part II: Discovering Aromatic (And Not So Aromatic) Compounds

In Part II we concentrate on aromatic systems, starting with the basics of structure and properties of benzene and then moving on to related aromatic compounds. We even throw in a section of spectroscopy of aromatic compounds. Chapters 7 and 8 finish up this part by going into detail about substitution reactions of aromatic compounds. You find out all you ever wanted to know (and maybe more) about electrophilic and nucleophilic substitutions, along with a little about elimination reactions.

Part III: Carbonyls: Good Alcohols Gone Bad

In Part III we cover that broad category of organic compounds called the carbonyls. First we give you an overview of carbonyl basics, including structure, reactivity, and spectroscopy. Then we go into more detail on aldehydes and ketones, enols and enolates, and carboxylic acids and their derivatives.

Part IV: Advanced Topics (Every Student’s Nightmare)

In Part IV we start by taking a closer look at nitrogen compounds and their structure, reactivity, and reactions. Then we move on to organometallic compounds, where we meet the infamous Grignard reaction. We then finish up this part by addressing some more-involved reactions of the carbonyls and biomolecules. You pick up some good hints for synthesis and roadmaps here.

Part V: Pulling It All Together

In Part V we show you how to pull all the previous information together and use it to develop strategies for designing synthesis reactions. We talk about both one-step and multistep synthesis as well as retrosynthetic analysis. Then we tackle the dreaded organic roadmaps. (We all wish we had an organic chemistry GPS here.)

Part VI: The Part of Tens

In this final part of the book we discuss ten surefire ways to flunk your organic chemistry class (so you know what to avoid) along with ten ways to increase your grade on those organic chemistry exams.

Icons Used in This Book

If you have ever read other For Dummies books (such as the wonderful Chemistry For Dummies or Biochemistry For Dummies, written by yours truly and published by Wiley), you recognize the icons used in this book. The following four icons can guide you to certain kinds of information:

This icon is a flag for those really important things that you shouldn’t forget as you go deeper into the world of organic chemistry.

We use this icon to alert you to a tip on the easiest or quickest way to learn a concept. Between the two of us, we have almost 70 years of teaching experience. We’ve learned a few tricks along the way and we don’t mind sharing.

The warning icon points to a procedure or potential outcome that can be dangerous. We call it our Don’t-Try-This-At-Home icon.

We try to avoid getting too technical throughout this book (believe it or not), but every now and then we can’t help but throw something in that is a little more in-depth than you might need. You won’t hurt your education by skipping it.

Where to Go from Here

The answer to this question really depends of your prior knowledge and goals. As with all For Dummies books, this one attempts to make all the chapters independent so that you can dive right into the material that’s causing you trouble without having to read other chapters first. If you feel comfortable with the topics covered in Organic Chemistry I, feel free to skip Part I. If you want a general overview of organic chemistry, skim the remainder of the book. Take a deeper plunge into a chapter when you find a topic that interests you or one in which you really need help.

And for all of you, no matter who you are or why you’re reading this book, we hope you have fun reading it and that it helps you to understand and appreciate organic chemistry.

Part I

Brushing Up on Important Organic Chemistry I Concepts

In this part . . .

Part I is a review of some general chemistry and Organic Chemistry I topics you need a firm grounding in before moving on to Organic Chemistry II. Different books and different instructors break Organic I and Organic II material at different places. We use the most common break, but some Part I material may, in fact, be new to you. Even if you covered these concepts last semester, some of them have a high vapor pressure and may have escaped between semesters.

We begin by bringing you up to speed on mechanisms and reminding you how to push electrons around with those curved arrows. We jog your memory with a discussion of substitution and elimination reactions and their mechanisms, in addition to free radical reactions. Next you review the structure, nomenclature, synthesis, and reactions of alcohols and ethers, and then you get to tackle conjugated unsaturated systems. Finally, we remind you of spectroscopic techniques, from the IR fingerprints to NMR shifts. The review in this part moves at a pretty fast pace, but we’re sure you can keep up.