| Author: |
T.W. Graham Solomons, Craig B. Fryhle & Scott A. Snyder
|
| Published in: | John Wiley & Sons |
| Release Year: | 2016 |
| ISBN: | 978-1-118-87576-6 |
| Pages: | 1293 |
| Edition: | Twelfth Edition |
| File Size: | 34 MB |
| File Type: | |
| Language: | English |
Description of Organic Chemistry
That’s what we want students to exclaim after they become acquainted with our subject. Our lives revolve around organic chemistry, whether we all realize it or not. When we understand organic chemistry, we see how life itself would be impossible without it, how the quality of our lives depends upon it, and how examples of organic chemistry leap out at us from every direction.
That’s why we can envision students enthusiastically exclaiming “It’s organic chemistry!” when, perhaps, they explain to a friend or family member how one central theme—organic chemistry— pervades our existence. We want to help students experience the excitement of seeing the world through an organic lens, and how the unifying and simplifying nature of organic chemistry helps make many things in nature comprehensible.
Our book makes it possible for students to learn organic chemistry well and to see the marvelous ways that organic chemistry touches our lives on a daily basis. Our book helps students develop their skills in critical thinking, problem-solving, and analysis—skills that are so important in today’s world, no matter what career paths they choose. The richness of organic chemistry lends itself to solutions for our time, from the fields of health care to energy, sustainability, and the environment. After all, it’s organic chemistry!
Energized by the power of organic chemistry and the goals of making our book an even more
efficient and relevant tool for learning, we have made a number of important changes in this Organic Chemistry edition.
We share the same goals and motivations as our colleagues in wanting to give students the best experience that they can have in organic chemistry. We also share the challenges of deciding what students need to know and how the material should be organized. In that spirit, our reviewers and adopters have helped guide a number of the changes that we have made in this Organic Chemistry edition. Simultaneously achieving efficiency and adding breadth We have redistributed and streamlined material from our old Chapter 21 about phenols, aryl halides, aryl ethers, benzyne, and nucleophilic aromatic substitution in a way that eliminates redundancy and places it in the context of other relevant material earlier in the book. At the same time, we wanted to update and add breadth to our book by creating a new Chapter 21, Transition Metal Complexes about transition metal organometallic compounds and their uses in organic synthesis.
Previously, transformations like the Heck-Mizoroki, Suzuki-Miyaura, Stille, Sonogashira, and olefin metathesis reactions had only been part of a special topic in our book, but as the exposure of undergraduates to these processes has become more widespread, we felt it essential to offer instructors a chapter that they could incorporate into their course if they wished. Streamlining and redistributing the content in our old Chapter 21 allowed us to do this, and we thank our reviewers for helping to prompt this change.
Transition metal organometallic complexes: Promoters of key bond-forming reactions Our new Chapter 21 brings students a well-rounded and manageable introduction to transition metal organometallic complexes and their use in organic synthesis. We begin the chapter with an introduction to the structure and common mechanistic steps of reactions involving transition metal organometallic compounds. We then introduce the essentials of important cross-coupling reactions such as the Heck-Mizoroki, Suzuki-Miyaura, Stille, Sonogashira, dialkylcuprate (Gilman), and olefin metathesis reactions at a level that is practical and useful for undergraduates. We intentionally organized the chapter so that instructors could move directly to the practical applications of these important reactions if they desire, skipping general background information on transition metal complexes if they wished.
Aromatic efficiency Our coverage of aromatic substitution reactions (Chapter 15) has been refocused by making our presentation of electrophilic aromatic substation more efficient at the same time as we included topics of nucleophilic aromatic substation and benzyne that had previously been in Chapter 21. Now all types of aromatic substitution reactions are combined in one chapter, with an enhanced flow that is exactly the same length as the old chapter solely on electrophilic aromatic reactions.
A focus on the practicalities of spectroscopy Students in an introductory organic chemistry course needs to know how to use spectroscopic data to explore structure more than they need to understand the theoretical underpinnings of spectroscopy. To that end, we have shortened Chapter 9, Nuclear Magnetic Resonance by placing aspects of NMR instrumentation and theory in a new special topic that is a standalone option for instructors and students. At the same time, we maintain our emphasis on using spectroscopy to probe structure by continuing to introduce IR in Chapter 2, Families of Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy, where students can learn to easily correlate functional groups with their respective infrared signatures and use IR data for problems in subsequent chapters.
Organizing nucleophilic substitution and elimination topics Some instructors find it pedagogically advantageous to present and assess their students’ knowledge of nucleophilic substitution reactions before they discuss elimination reactions. Following the advice of some reviewers, we have adjusted the transition between Chapters 6, Nucleophilic Reactions: Properties and Substitution Reactions of Alkyl Halides and 7, Alkenes and Alkynes I: Properties and Synthesis ; Elimination Reactions of Alkyl Halides so that an instructor can pause cleanly after Chapter 6 to give an assessment on substitution, or flow directly into Chapter 7 on elimination reactions if they wish.
Synthesizing the Material The double entendre in the name of our new Synthesizing the Material problems is not lost in the ether. In this new group of problems, found at the end of Chapters 6-21, students are presented with either multistep synthetic transformations and unknown products, or target molecules whose precursors they must deduce by retrosynthetic analysis. Problems in our Synthesizing the Material groups often call upon reagents and transformations covered in prior chapters. Thus, while students work on synthesizing a chemical material, they are also synthesizing knowledge.
Content of Organic Chemistry
1 The Basics of Bonding and Molecular Structure 1
2 Families of Carbon Compounds Functional Groups, Intermolecular Forces, and Infrared (IR)
Spectroscopy 55
3 Acids and Bases An Introduction to Organic Reactions and Their Mechanisms 104
4 Nomenclature and Conformations of Alkanes and Cycloalkanes 144
5 Stereochemistry Chiral Molecules 193
6 Nucleophilic Reactions Properties and Substitution Reactions of Alkyl Halides 240
7 Alkenes and Alkynes I Properties and Synthesis. Elimination Reactions of Alkyl Halides 282
8 Alkenes and Alkynes II Addition Reactions 337
9 Nuclear Magnetic Resonance and Mass Spectrometry Tools for Structure Determination 391
10 Radical Reactions 448
11 Alcohols and Ethers Synthesis and Reactions 489
12 Alcohols from Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds 534
13 Conjugated Unsaturated Systems 572
14 Aromatic Compounds 617
15 Reactions of Aromatic Compounds 660
16 Aldehydes and Ketones Nucleophilic Addition to the Carbonyl Group 711
17 Carboxylic Acids and Their Derivatives Nucleophilic Addition–Elimination at the Acyl Carbon 761
18 Reactions at the α Carbon of Carbonyl Compounds Enols and Enolates 811
19 Condensation and Conjugate Addition Reactions of Carbonyl Compounds More
Chemistry of Enolates 849
20 Amines 890
21 Transition Metal Complexes Promoters of Key Bond-Forming Reactions 938
22 Carbohydrates 965
23 Lipids 1011
24 Amino Acids and Proteins 1045
25 Nucleic Acids and Protein Synthesis 1090
Glossary GL-1
Index I-1
2 Families of Carbon Compounds Functional Groups, Intermolecular Forces, and Infrared (IR)
Spectroscopy 55
3 Acids and Bases An Introduction to Organic Reactions and Their Mechanisms 104
4 Nomenclature and Conformations of Alkanes and Cycloalkanes 144
5 Stereochemistry Chiral Molecules 193
6 Nucleophilic Reactions Properties and Substitution Reactions of Alkyl Halides 240
7 Alkenes and Alkynes I Properties and Synthesis. Elimination Reactions of Alkyl Halides 282
8 Alkenes and Alkynes II Addition Reactions 337
9 Nuclear Magnetic Resonance and Mass Spectrometry Tools for Structure Determination 391
10 Radical Reactions 448
11 Alcohols and Ethers Synthesis and Reactions 489
12 Alcohols from Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds 534
13 Conjugated Unsaturated Systems 572
14 Aromatic Compounds 617
15 Reactions of Aromatic Compounds 660
16 Aldehydes and Ketones Nucleophilic Addition to the Carbonyl Group 711
17 Carboxylic Acids and Their Derivatives Nucleophilic Addition–Elimination at the Acyl Carbon 761
18 Reactions at the α Carbon of Carbonyl Compounds Enols and Enolates 811
19 Condensation and Conjugate Addition Reactions of Carbonyl Compounds More
Chemistry of Enolates 849
20 Amines 890
21 Transition Metal Complexes Promoters of Key Bond-Forming Reactions 938
22 Carbohydrates 965
23 Lipids 1011
24 Amino Acids and Proteins 1045
25 Nucleic Acids and Protein Synthesis 1090
Glossary GL-1
Index I-1
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