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Topic 2 - Introduction to Organic Reactions

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Bruice 5th Edition

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Organic chemistry studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding. The study of structure determines their chemical composition and formula and the study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical (in silico) study.

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Organic chemistry studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding. The study of structure determines their chemical composition and formula and the study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior.

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What Is Organic Chemistry?

Organic chemistry is the study of the structure, properties, composition, reactions, and preparation of carbon-containing compounds, which include not only hydrocarbons but also compounds with any number of other elements, including hydrogen (most compounds contain at least one carbon-hydrogen bond), nitrogen, oxygen, halogens, phosphorus, silicon, and sulfur. This branch of chemistry was originally limited to compounds produced by living organisms but has been broadened to include human-made substances such as plastics. The range of application of organic compounds is enormous and also includes, but is not limited to, pharmaceuticals, petrochemicals, food, explosives, paints, and cosmetics.

Where Is Organic Chemistry Used?

Organic chemistry is a highly creative science in which chemists create new molecules and explore the properties of existing compounds. It is the most popular field of study for ACS chemists and Ph.D. chemists.

Organic compounds are all around us. They are central to the economic growth of the United States in the rubber, plastics, fuel, pharmaceutical, cosmetics, detergent, coatings, dyestuff, and agrichemical industries, to name a few. The very foundations of biochemistry, biotechnology, and medicine are built on organic compounds and their role in life processes. Many modern, high-tech materials are at least partially composed of organic compounds .

Organic chemists spend much of their time creating new compounds and developing better ways of synthesizing previously known compounds.

Which Industries Hire Organic Chemists?

Organic chemists at all levels are generally employed by pharmaceutical, biotech, chemical, consumer product, and petroleum industries. Chemists in industry mainly work in development, while chemists in academia are involved in more basic research. The federal (e.g., Food and Drug Administration, Patent and Trademark Office) state, and local governments also hire organic chemists.

Biotechnology

Biotechnology ("biotech" for short) is a field of applied biology that involves using living organisms and bioprocesses to create or modify products for a specific use. The cultivation of plants has been viewed as the earliest example of biotechnology and the precursor to modern genetic engineering and cell and tissue culture technologies. Virtually all biotechnology products are the result of organic chemistry.

Biotechnology is used in in health care, crop production and agriculture, nonfood uses of crops and other products (e.g., biodegradable plastics, vegetable oil, biofuels), and environmental applications.

Biotechnology Companies:
GenenTech, Monsanto, Dow AgroSciences, Cargill

These companies make products such as seeds for crops that are resistant to certain diseases, seed coatings with specific properties, and plants that are drought resistant.

Chemical

The chemical industry is crucial to modern world economies and works to convert raw materials such as oil, natural gas, air, water, metals, and minerals into more than 70,000 different products. These base products are then used to make consumer products in addition to manufacturing, service, construction, agriculture, and other industries.

Over three-fourths of the chemical industry's output worldwide is polymers and plastics. Chemicals are used to make a wide variety of consumer goods, as well as thousands of products that are inputs to the agriculture, manufacturing, construction, and service industries. The chemical industry itself consumes about a quarter of its own output. Major industrial customers include rubber and plastic products, textiles, apparel, petroleum refining, pulp and paper, and primary metals.

Chemical companies:
BASF, Bayer, Braskem, Celanese, Dow, DuPont, Eastman

Consumer Products

Consumer products companies make consumer products for everyday use, such as soaps, detergents, cleaning products, plastic goods, and cosmetics.

Consumer products companies:
PPG Industries, DuPont, Mitsubishi Chemical, Johnson & Johnson

Petroleum

The petroleum industry includes the global processes of exploration, extraction, refining, transporting, and marketing petroleum products. The largest volume products of the industry are fuel oil and gasoline. Petroleum is also the raw material for many chemical products, including pharmaceuticals, solvents, fertilizers, pesticides, and plastics. The industry is usually divided into three major components: upstream (exploration and production), midstream (transportation), and downstream (refining crude oil, processing and purifying natural gas, creating petrochemicals).

Petroleum companies:
ExxonMobil, Shell Chemicals, Chevron Phillips Chemial Company, BP

Pharmaceutical

The pharmaceutical industry develops, produces, and markets drugs licensed for use as medications for humans or animals. Some pharmaceutical companies deal in brand-name (i.e., has a trade name and can be produced and sold only by the company holding the patent) and/or generic (i.e., chemically equivalent, lower-cost version of a brand- name drug) medications and medical devices (agents that act on diseases without chemical interaction with the body). Pharmaceuticals (brand name and generic) and medical devices are subject to a large number of country-specific laws and regulations regarding patenting, testing, safety assurance, efficacy, monitoring, and marketing.

Pharmaceuticals companies:
Pfizer, Novartis, Merck, Bayer, GlaxoSmithKline, Johnson & Johnson, Sanofi, Hoffman-LaRoche, AstraZeneca, and Abbott Laboratories.

Career Areas for Organic Chemists

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Organic Chemistry - American Chemical Society

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To get the best possible experience using our website, we recommend that you upgrade to latest version of this browser or install another web browser. See our Browser Support/Compatibility page for supported browsers list. ACS is committed to helping combat the global COVID-19 pandemic with initiatives and free resources.

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Description
For courses in Organic Chemistry (2-Semester) A framework for organic chemistry built around the similarities in reaction types
Paula Bruice's presentation in Organic Chemistry, Eighth Edition provides mixed-science majors with the conceptual foundations, chemical logic, and problem-solving skills they need to reason their way to solutions for diverse problems in synthetic organic chemistry, biochemistry, and medicine. The Eighth Edition builds a strong framework for thinking about organic chemistry by unifying principles of reactivity that students will apply throughout the course, discouraging memorization. With more applications than any other textbook, Dr. Bruice consistently relates structure and reactivity to what occurs in our own cells and reinforces the fundamental reason for all chemical reactions-electrophiles react with nucleophiles. New streamlined coverage of substitution and elimination, updated problem-solving strategies, synthesis skill-building applications and tutorials guide students throughout fundamental and complex content in both the first and second semesters of the course.

MasteringChemistry™ is not included. Students, if MasteringChemistry is a recommended/mandatory component of the course, please ask your instructor for the correct ISBN. MasteringChemistry should only be purchased when required by an instructor. Instructors, contact your Pearson representative for more information.

MasteringChemistry an online homework, tutorial, and assessment program designed to work with this text to engage students and improve results. Interactive, self-paced tutorials provide individualized coaching to help students stay on track. With a wide range of activities available, students can actively learn, understand, and retain even the most difficult concepts.

Features

This title is a Pearson Global Edition. The Editorial team at Pearson has worked closely with educators around the world to include content which is especially relevant to students outside the United States.

About the Book
A modern, streamlined organization emphasizes unifying principles of reactivity, offering an economy of presentation and discouraging memorization

The text consistently highlights the fundamental reason for all chemical reactions - electrophiles combine with nucleophiles - in order to keep students focused on the key ideas.

Students are introduced to synthetic and retrosynthetic chemistry early on, allowing them to grasp multistep synthesis from the beginning.

The textbook bridges the gap between organic chemistry and biochemistry
Because bioorganic chemistry is the bridge between organic chemistry and biochemistry, the text emphasizes that the organic reactions that chemists carry out in the laboratory are similar to those performed by nature inside a cell. These connections are especially important to biological science majors.

In Chapters 1-20, the bioorganic material is presented as "interest boxes" and within the last sections of the chapters so that this material is available to the student without requiring the instructor to introduce bioorganic topics into the course.

Chapters 21-26 focus on the organic chemistry of living systems. These chapters have the unique distinction of containing more chemistry than is typically found in the corresponding parts of a biochemistry text.

UPDATED! Revised, accuracy-checked text provides increased exam relevancy
To better prepare students for the MCAT exam, MCAT learning outcomes and MCAT-style questions have been added to the Student's Study Guide and Solutions Manual, as well as MasteringChemistry.
NEW! Improved visuals and organization engage students with difficult subject matter, organizes the chapter content and improves ease of use:

NEW! Expanded annotations reinforce the revised art program and help keep students focused on the most important material.

NEW! Numerous subheads are part of a redesigned text that enhances ease of use and gives the text a modern look and feel. Subheads help students locate important topics, show how that content develops within the section, and break the presentation into "bite-sized" portions that are easier to comprehend and connect.

Strengthened emphasis on the strategies needed to solve problems and master the content
Passages explaining important problem-solving strategies - content the student must learn - are clearly labeled with a LEARN THE STRATEGY label. Follow-up problems that require students to apply the just learned strategy are labeled with a USE THE STRATEGY label. These labels, which are implemented throughout the entire text, allow students to easily find important content and practice its use.
NEW and UPDATED! New and restructured features give students additional conceptual and skill building support

UPDATED! Tutorial spreads and Design a Synthesis sections explicitly highlight essential skills.

NEW! Marginal notes highlighting relative reactivity and the Organizing What We Know feature now align with each other to better relate skill building to conceptual understanding.

Newly highlighted Problem-Solving Strategies guide students on how to approach various problems and help to develop critical thinking skills. See more at:

http://catalogue.pearsoned.co.uk/educator/product/Organic-Chemistry-plus-MasteringChemistry-withPearson-eText-GlobalEdition/9781292160450.page

Seven special Design A Synthesis sections introduce and help students through the iterative process of solving complex problems.

End of chapter Problems review key topics and reinforce essential skills.

End of chapter Reaction Summaries ensure students fully grasp how each reaction occurs.

NEW and UPDATED! Applications boxes connect the discussion to Medical, Environmental, Biological, Pharmaceutical, Nutritional, Chemical, Industrial, Historical, and General applications, and help students relate the material to real life and potential future careers. Bruice provides more of this kind of material than any other competing text on the market.

Redesigned! Organizing What We Know about the Reactions of Organic Compounds Table
This informative and powerful table summarizes Bruice's approach to teaching organic chemistry by categorizing all organic reactions into four groups having similar chemical behavior.
Content Updates and Revisions to the Table of Contents streamline and improve clarity in the presentation.

Using the E,Z system to name alkenes was moved to Chapter 4, so it appears immediately after using cis, trans to distinguish alkene stereoisomers.

Catalytic hydrogenation and relative stabilities of alkenes was moved from Chapter 6 to Chapter 5 (thermodynamics), so it can be used to illustrate how H° values can be used to determine relative stabilities. As a result, all the reactions in Chapter 6 have well-defined mechanisms where the first step in each of them is addition of the electrophile to the sp 2 carbon bonded to the most hydrogens.

NEW! The two chapters in the previous edition on Substitution and Elimination reactions of alkenes have been combined into one chapter (Chapter 9). The recent compelling evidence showing that alkyl halides do not undergo SN1 solvolysis reactions has allowed this material to be greatly simplified, so now it fits nicely into one chapter.

The structure of benzene is covered in Chapter 8 (the chapter on resonance) because it is the ideal compound to use to explain the concept of delocalized electrons. A discussion on aromaticity is also found in this chapter, so a short introduction to electrophilic aromatic substitution reactions is now included. This allows students to see how aromaticity causes benzene to undergo electrophilic substitution rather than electrophilic addition-the reactions they have just finished studying.

NEW! Electronic effects are discussed in Chapter 8 and used to teach students how substituents affect the pK a values of phenols, benzoic acids, and anilinium ions. Electronic effects are then reviewed in the chapter on benzene.

Electronic effects can help students understand the directing effects of substituents on benzene rings. With the Eighth Edition, electronic effects are discussed in Chapter 8 in order to teach students how substituents affect the pK a values of phenols, benzoic acids, and anilinium ions. Electronic effects are then reviewed in the chapter on benzene.

NEW! Chapter on Lipids. The lipid material previously in the chapter on carboxylic acids and their derivatives (fatty acids, waxes, phospholipids, etc.) has been moved into a new chapter to help students see that the outcome of all reactions in the chapter could be determined simply by understanding how a tetrahedral intermediate partitions. The discussion of terpenes from the metabolism chapter has also been moved into this chapter, along with some new material.

The IR spectra have been updated throughout the text and the solutions manual while additional spectroscopy problems have been added to the solutions manual. Bruice's Study Guide and Solutions Manual now offers a diverse group of 60 spectroscopy problems.

Group I: electrophilic addition reactions

Group II: nucleophilic substitution reactions and elimination reactions

Group III: nucleophilic ddition reactions and nucleophilic addition-elimination reactions

Group IV: electrophilic (and nucleophilic) aromatic substitution reactions

The table builds as students gain knowledge about groups of organic compounds as they work through the text. The easy to interpret table emphasizes the key characteristics common to the group of organic compounds covered in preceding chapters.

Contributing author Richard Morrison, University of Georgia, has reviewed and honed the problem solving presentations, end of chapter problems, and the solutions manual.
Before Class
Pearson eText features include:
Instructor and student note taking, highlighting, bookmarking, and search

During Class
NEW! Learning Catalytics™ generates class discussion, guides your lecture, and promotes peer-to-peer learning with real-time analytics. MasteringChemistry with eText now provides Learning Catalytics-an interactive student response tool that uses students' smartphones, tablets, or laptops to engage them in more sophisticated tasks and thinking. Instructors can:

Pose a variety of open-ended questions that help students develop critical thinking skills around structure and reactivity in organic chemistry with 10 new Learning Catalytics questions for each chapter of Organic Chemistry, Eighth Edition.

Monitor responses to find out where students are struggling

Use real-time data to adjust the instructional strategy and engage students during class

Manage student interactions by automatically grouping students for discussion, teamwork, and peer-to-peer learning

After Class

Chapter 21 Amino Acids, Peptides, And Proteins

Chapter 22 Catalysis In Organic Reactions And In Enzymatic

Chapter 23 The Organic Mechanisms Of The Coenzymes, Compounds Derived From Vitamins

Chapter 24 The Organic Chemistry Of The Metabolic Pathways

Chapter 25 The Organic Chemistry Of Lipids

Chapter 26 The Chemistry Of The Nucleic Acids

MasteringChemistry™ is not included. Students, if MasteringChemistry is a recommended/mandatory component of the course, please ask your instructor for the correct ISBN. MasteringChemistry should only be purchased when required by an instructor. Instructors, contact your Pearson representative for more information.
About the Book The textbook bridges the gap between organic chemistry and biochemistry
Mastering brings learning full circle by continuously adapting to each student and making learning more personal than ever-before, during, and after class.

In Chapters 1-20, the bioorganic material is presented as "interest boxes" and within the last sections of the chapters so that this material is available to the student without requiring the instructor to introduce bioorganic topics into the course.

Chapters 21-26 focus on the organic chemistry of living systems. These chapters have the unique distinction of containing more chemistry than is typically found in the corresponding parts of a biochemistry text.

UPDATED! Revised, accuracy-checked text provides increased exam relevancy
To better prepare students for the MCAT exam, MCAT learning outcomes and MCAT-style questions have been added to the Student's Study Guide and Solutions Manual, as well as MasteringChemistry.
NEW! Improved visuals and organization engage students with difficult subject matter, organizes the chapter content and improves ease of use:

Expanded annotations reinforce the revised art program and help keep students focused on the most important material.

Numerous subheads are part of a redesigned text that enhances ease of use and gives the text a modern look and feel. Subheads help students locate important topics, show how that content develops within the section, and break the presentation into "bite-sized" portions that are easier to comprehend and connect.

Strengthened emphasis on the strategies needed to solve problems and master the content
Passages explaining important problem-solving strategies - content the student must learn - are clearly labeled with a LEARN THE STRATEGY label. Follow-up problems that require students to apply the just learned strategy are labeled with a USE THE STRATEGY label. These labels, which are implemented throughout the entire text, allow students to easily find important content and practice its use.
NEW and UPDATED! New and restructured features give students additional conceptual and skill building support

UPDATED! Tutorial spreads and Design a Synthesis sections explicitly highlight essential skills.

NEW! Marginal notes highlighting relative reactivity and the Organizing What We Know feature now align with each other to better relate skill building to conceptual understanding.

Newly highlighted Problem-Solving Strategies guide students on how to approach various problems and help to develop critical thinking skills. See more at: http://www.pearsonhighered.com/educator/product/Organic-Chemistry-Plus-MasteringChemistry-with-eText-Access-Card-Package/9780321803078.page#sthash.8kPWNcIB.dpuf

Seven special Design A Synthesis sections introduce and help students through the iterative process of solving complex problems.

End of chapter Problems review key topics and reinforce essential skills.

End of chapter Reaction Summaries ensure students fully grasp how each reaction occurs.

NEW and UPDATED! Applications boxes connect the discussion to Medical, Environmental, Biological, Pharmaceutical, Nutritional, Chemical, Industrial, Historical, and General applications, and help students relate the material to real life and potential future careers. Bruice provides more of this kind of material than any other competing text on the market.

Redesigned! Organizing What We Know about the Reactions of Organic Compounds Table
This informative and powerful table summarizes Bruice's approach to teaching organic chemistry by categorizing all organic reactions into four groups having similar chemical behavior.
Content Updates and Revisions to the Table of Contents streamline and improve clarity in the presentation.

Using the E,Z system to name alkenes was moved to Chapter 4, so it appears immediately after using cis, trans to distinguish alkene stereoisomers.

Catalytic hydrogenation and relative stabilities of alkenes was moved from Chapter 6 to Chapter 5 (thermodynamics), so it can be used to illustrate how H° values can be used to determine relative stabilities. As a result, all the reactions in Chapter 6 have well-defined mechanisms where the first step in each of them is addition of the electrophile to the sp 2 carbon bonded to the most hydrogens.

NEW! The two chapters in the previous edition on Substitution and Elimination reactions of alkenes have been combined into one chapter (Chapter 9). The recent compelling evidence showing that alkyl halides do not undergo SN1 solvolysis reactions has allowed this material to be greatly simplified, so now it fits nicely into one chapter.

The structure of benzene is covered in Chapter 8 (the chapter on resonance) because it is the ideal compound to use to explain the concept of delocalized electrons. A discussion on aromaticity is also found in this chapter, so a short introduction to electrophilic aromatic substitution reactions is now included. This allows students to see how aromaticity causes benzene to undergo electrophilic substitution rather than electrophilic addition-the reactions they have just finished studying.

NEW! Electronic effects are discussed in Chapter 8 and used to teach students how substituents affect the pK a values of phenols, benzoic acids, and anilinium ions. Electronic effects are then reviewed in the chapter on benzene.

Electronic effects can help students understand the directing effects of substituents on benzene rings. With the Eighth Edition, electronic effects are discussed in Chapter 8 in order to teach students how substituents affect the pK a values of phenols, benzoic acids, and anilinium ions. Electronic effects are then reviewed in the chapter on benzene.

NEW! Chapter on Lipids. The lipid material previously in the chapter on carboxylic acids and their derivatives (fatty acids, waxes, phospholipids, etc.) has been moved into a new chapter to help students see that the outcome of all reactions in the chapter could be determined simply by understanding how a tetrahedral intermediate partitions. The discussion of terpenes from the metabolism chapter has also been moved into this chapter, along with some new material.

The IR spectra have been updated throughout the text and the solutions manual while additional spectroscopy problems have been added to the solutions manual. Bruice's Study Guide and Solutions Manual now offers a diverse group of 60 spectroscopy problems.

Group I: electrophilic addition reactions

Group II: nucleophilic substitution reactions and elimination reactions

Group III: nucleophilic ddition reactions and nucleophilic addition-elimination reactions

Group IV: electrophilic (and nucleophilic) aromatic substitution reactions

The table builds as students gain knowledge about groups of organic compounds as they work through the text. The easy to interpret table emphasizes the key characteristics common to the group of organic compounds covered in preceding chapters.

Contributing author Richard Morrison, University of Georgia, has reviewed and honed the problem solving presentations, end of chapter problems, and the solutions manual.
Before Class

Chapter 21 Amino Acids, Peptides, And Proteins

Chapter 22 Catalysis In Organic Reactions And In Enzymatic

Chapter 23 The Organic Mechanisms Of The Coenzymes, Compounds Derived From Vitamins

Chapter 24 The Organic Chemistry Of The Metabolic Pathways

Chapter 25 The Organic Chemistry Of Lipids

Chapter 26 The Chemistry Of The Nucleic Acids

Instructor and student note taking, highlighting, bookmarking, and search
During Class
Learning Catalytics™ generates class discussion, guides your lecture, and promotes peer-to-peer learning with real-time analytics. MasteringChemistry with eText now provides Learning Catalytics-an interactive student response tool that uses students' smartphones, tablets, or laptops to engage them in more sophisticated tasks and thinking. Instructors can:

Pose a variety of open-ended questions that help students develop critical thinking skills around structure and reactivity in organic chemistry with 10 new Learning Catalytics questions for each chapter of Organic Chemistry, Eighth Edition.

Monitor responses to find out where students are struggling

Use real-time data to adjust the instructional strategy and engage students during class

Manage student interactions by automatically grouping students for discussion, teamwork, and peer-to-peer learning

After Class

NEW! MasteringChemistry's Organic Chemistry Drawing Tool is a customized version of Java Free MarvinSketch that accommodates the diversity of structures and reaction mechanisms inherent to learning organic chemistry while providing students with a wrong answer specific feedback. This educational version of MarvinSketch has been customized in response to input from hundreds of undergraduate students. The drawing tool includes comprehensive MasteringChemistry tutorials, specific to drawing with MarvinSketch, that equip students to start quickly drawing organic structures and mechanisms to complete homework. The tutorials cover how to accurately draw reaction mechanisms, how to modify answers, and how to use the palette. All mechanism-based problems provide feedback specific to each step of the reaction, and new visual cues help clarify exact placement of arrows, enable selection of the electron, and highlight which bonds have been formed or broken.

Assignable, textbook specific skill building tutorials guide students through the toughest topics in organic chemistry including:

Acids and Bases (after chapter 2)

Using Molecular Models (after Chapter 3)

Interconverting Structural Representations (after Chapter 4)

Drawing Curved Arrows (after Chapter 5)

Drawing Resonance Contributors (after chapter 8)

Drawing Curved Arrows in Radical Systems (after Chapter 13)

Synthesis and Retrosynthetic Analysis (after Chapter 17)

Rate Changes and Kinetics (Appendix II)

NEW! Six NMR/IR Spectroscopy simulations (a partnership with ACD labs) allow professors and students access to limitless spectral analysis with guided activities that can be used in the lab, in the classroom, or after class to study and explore spectra virtually. Activities authored by Mike Huggins, University of West Florida, prompt students to utilize the spectral simulator and walk them through different analyses and possible conclusions.

120 Organic Chemistry-specific tutorials built around the most challenging topics in Organic Chemistry provide wrong answer specific feedback and Socratic and declarative hints so students learn where they are going wrong.

1500 automatically graded questions can be assigned as homework or practice. These questions are specific to the Eighth Edition and the majority requires drawing structures and reactions.

Enhanced end-of-chapter problems now include wrong-answer specific feedback on all mechanism problems so students have the opportunity to practice and test their understanding of organic reactivity outside of class with the help and ease of an updated drawing tool and detailed feedback on their work.

New to this Edition
PART ONE: An Introduction to the Study of Organic Chemistry
Because bioorganic chemistry is the bridge between organic chemistry and biochemistry, the text emphasizes that the organic reactions that chemists carry out in the laboratory are similar to those performed by nature inside a cell. These connections are especially important to biological science majors.

MasteringChemistry™ is not included. Students, if MasteringChemistry is a recommended/mandatory component of the course, please ask your instructor for the correct ISBN. MasteringChemistry should only be purchased when required by an instructor. Instructors, contact your Pearson representative for more information.

Mastering brings learning full circle by continuously adapting to each student and making learning more personal than ever-before, during, and after class.

Pearson eText features include:
PART TWO: Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization

NEW! MasteringChemistry's Organic Chemistry Drawing Tool is a customized version of Java Free MarvinSketch that accommodates the diversity of structures and reaction mechanisms inherent to learning organic chemistry while providing students with a wrong answer specific feedback. This educational version of MarvinSketch has been customized in response to input from hundreds of undergraduate students. The drawing tool includes comprehensive MasteringChemistry tutorials, specific to drawing with MarvinSketch, that equip students to start quickly drawing organic structures and mechanisms to complete homework. The tutorials cover how to accurately draw reaction mechanisms, how to modify answers, and how to use the palette. All mechanism-based problems provide feedback specific to each step of the reaction, and new visual cues help clarify exact placement of arrows, enable selection of the electron, and highlight which bonds have been formed or broken.

Assignable, textbook specific skill building tutorials guide students through the toughest topics in organic chemistry including:

Acids and Bases (after chapter 2)

Using Molecular Models (after Chapter 3)

Interconverting Structural Representations (after Chapter 4)

Drawing Curved Arrows (after Chapter 5)

Drawing Resonance Contributors (after chapter 8)

Drawing Curved Arrows in Radical Systems (after Chapter 13)

Synthesis and Retrosynthetic Analysis (after Chapter 17)

Rate Changes and Kinetics (Appendix II)

Six NMR/IR Spectroscopy simulations (a partnership with ACD labs) allow professors and students access to limitless spectral analysis with guided activities that can be used in the lab, in the classroom, or after class to study and explore spectra virtually. Activities authored by Mike Huggins, University of West Florida, prompt students to utilize the spectral simulator and walk them through different analyses and possible conclusions.

Enhanced end-of-chapter problems now include wrong-answer specific feedback on all mechanism problems so students have the opportunity to practice and test their understanding of organic reactivity outside of class with the help and ease of an updated drawing tool and detailed feedback on their work.

Table of Contents

1. Remembering General Chemistry: Electronic Structure and Bonding

2. Acids and Bases: Central to Understanding Organic Chemistry

TUTORIAL: Acids and Bases

3. An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure

TUTORIAL: Using Molecular Models

4. Isomers: The Arrangement of Atoms in Space

TUTORIAL: Interconverting Structural Representations
PART THREE: Substitution and Elimination Reactions
5. Alkenes: Structure, Nomenclature, and an Introduction to Reactivity * Thermodynamics and Kinetics

TUTORIAL: Drawing Curved Arrows

6. The Reactions of Alkenes * The Stereochemistry of Addition Reactions

7. The Reactions of Alkynes * An Introduction to Multistep Synthesis

8. Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction * Aromaticity and Electronic Effects: An Introduction the Reactions of Benzene
PART FOUR: Identification of Organic Compounds
TUTORIAL: Drawing Resonance Contributors

9. Substitution and Elimination Reactions of Alkyl Halides
PART FIVE: Carbonyl Compounds
10. Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds

11. Organometallic Compounds

12. Radicals

TUTORIAL: Drawing Curved Arrows in Radical Systems
PART SIX: Aromatic Compounds
13. Mass Spectrometry; Infrared Spectroscopy; and UV/Vis Spectroscopy

14. NMR Spectroscopy
PART SEVEN: Bioorganic Compounds
15. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

16. Reactions of Aldehydes and Ketones * More Reactions of Carboxylic Acid Derivatives

17. Reactions at the α-Carbon

TUTORIAL: Synthesis and Retrosynthetic Analysis

18. Reactions of Benzene And Substituted Benzenes

19. More About Amines * Reactions of Heterocyclic Compounds

20. The Organic Chemistry Of Carbohydrates
PART EIGHT: Special Topics in Organic Chemistry
21. Amino Acids, Peptides, and Proteins

22. Catalysis in Organic Reactions and in Enzymatic Reactions

23. The Organic Chemistry of the Coenzymes, Compounds Derived from Vitamins

24. The Organic Chemistry of the Metabolic Pathways

25. The Organic Chemistry of Lipids

26. The Chemistry of the Nucleic Acids

27. Synthetic Polymers

28. Pericyclic Reactions

Appendix I - pKa Values

Appendix II - Kinetics

Appendix III - Summary of Methods Used to Synthesize a Particular Functional Group

Appendix IV - Summary of Methods Employed to Form Carbon-Carbon Bonds

Appendix V - Spectroscopy Tables

Appendix VI - Physical Properties of Organic Compounds

Appendix VII - Answers to Selected Problems

# data[].attributes.attachment_link.description
For courses in Organic Chemistry (2-Semester) A framework for organic chemistry built around the similarities in reaction types Paula Bruice's presentation in Organic Chemistry, Eighth Edition provides mixed-science majors with the conceptual foundations, chemical logic, and problem-solving skills they need to reason their way to solutions for diverse problems in synthetic organic chemistry, biochemistry, and medicine.

# data[].attributes.attachment_link.readable_text
Bonding and Molecular Structure 1

1.1 Life and the Chemistry of Carbon Compounds-We Are Stardust 2

The Chemistry of... Natural Products 3

1.2 Atomic Structure 3

1.3 Chemical Bonds: The Octet Rule 5

1.4 How To Write Lewis Structures 7

1.5 Formal Charges and How To Calculate Them 12

1.6 Isomers: Different Compounds that Have the Same Molecular Formula 14

1.7 How To Write and Interpret Structural Formulas 15

1.8 Resonance Theory 22

1.9 Quantum Mechanics and Atomic Structure 27

1.10 Atomic Orbitals and Electron Configuration 28

1.11 Molecular Orbitals 30

1.12 The Structure of Methane and Ethane: sp3 Hybridization 32

The Chemistry of... Calculated Molecular Models: Electron Density Surfaces 36

1.13 The Structure of Ethene (Ethylene): sp 2 Hybridization 36

1.14 The Structure of Ethyne (Acetylene): sp Hybridization 40

1.15 A Summary of Important Concepts that Come from Quantum Mechanics 43

1.16 How To Predict Molecular Geometry: The Valence Shell Electron Pair Repulsion Model 44

1.17 Applications of Basic Principles 47
2 Families of Carbon
Compounds Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy 55

2.1 Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds 56

2.2 Polar Covalent Bonds 59

2.3 Polar and Nonpolar Molecules 61

2.4 Functional Groups 64

2.5 Alkyl Halides or Haloalkanes 65

2.6 Alcohols and Phenols 67

2.7 Ethers 69

The Chemistry of... Ethers as General Anesthetics 69

2.8 Amines 70

2.9 Aldehydes and Ketones 71

2.10 Carboxylic Acids, Esters, and Amides 73

2.11 Nitriles 75

2.12 Summary of Important Families of Organic Compounds 76

2.13 Physical Properties and Molecular Structure 77

The Chemistry of... Fluorocarbons and Teflon 81

2.14 Summary of Attractive Electric Forces 85

The Chemistry of... Organic Templates Engineered to Mimic Bone Growth 86

2.15 Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups 86

2.16 Interpreting IR Spectra 90

2.17 Applications of Basic Principles 97
3 Acids and Bases
An Introduction to Organic Reactions and Their Mechanisms 104

3.1 Acid-Base Reactions 105

3.2 How To Use Curved Arrows in Illustrating Reactions 107

3.3 Lewis Acids and Bases 109

3.4 Heterolysis of Bonds to Carbon: Carbocations and Carbanions 111

3.5 The Strength of Brønsted-Lowry Acids and Bases: Ka and pKa 113

3.6 How To Predict the Outcome of Acid-Base Reactions 118

3.7 Relationships between Structure and Acidity 120

3.8 Energy Changes 123

3.9 The Relationship between the Equilibrium Constant and the Standard Free-Energy Change, ΔG ° 125

3.10 Acidity: Carboxylic Acids versus Alcohols 126

3.11 The Effect of the Solvent on Acidity 132

3.12 Organic Compounds as Bases 132

3.13 A Mechanism for an Organic Reaction 134

3.14 Acids and Bases in Nonaqueous Solutions 135

3.15 Acid-Base Reactions and the Synthesis of

Deuterium- and Tritium-Labeled Compounds 136

3.16 Applications of Basic Principles 137
4 Nomenclature and Conformations of Alkanes and Cycloalkanes
4.1 Introduction to Alkanes and Cycloalkanes 145

The Chemistry of... Petroleum Refining 145

4.2 Shapes of Alkanes 146

4.3 How To Name Alkanes, Alkyl Halides, and Alcohols: The IUPAC System 148

4.4 How to Name Cycloalkanes 155

4.5 How To Name Alkenes and Cycloalkenes 158

4.6 How To Name Alkynes 160

4.7 Physical Properties of Alkanes and Cycloalkanes 161

The Chemistry of... Pheromones: Communication by Means of Chemicals 163

4.8 Sigma Bonds and Bond Rotation 164

4.9 Conformational Analysis of Butane 166

The Chemistry of... Muscle Action 168

4.10 The Relative Stabilities of Cycloalkanes: Ring Strain 168

4.11 Conformations of Cyclohexane: The Chair and the Boat 170

The Chemistry of... Nanoscale Motors and Molecular Switches 172

4.12 Substituted Cyclohexanes: Axial and Equatorial Hydrogen Groups 173

4.13 Disubstituted Cycloalkanes: Cis-Trans Isomerism 177

4.14 Bicyclic and Polycyclic Alkanes 181

4.15 Chemical Reactions of Alkanes 182

4.16 Synthesis of Alkanes and Cycloalkanes 182

4.17 How To Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency 184

4.18 Applications of Basic Principles 186
5 Stereochemistry
Chiral Molecules 193

5.1 Chirality and Stereochemistry 194

5.2 Isomerism: Constitutional Isomers and Stereoisomers 195

5.3 Enantiomers and Chiral Molecules 197

5.4 Molecules Having One Chirality Center are Chiral 198

5.5 More about the Biological Importance of Chirality 201

5.6 How To Test for Chirality: Planes of Symmetry 203

5.7 Naming Enantiomers: The R,S-System 204

5.8 Properties of Enantiomers: Optical Activity 208

5.9 Racemic Forms 213

5.10 The Synthesis of Chiral Molecules 214

5.11 Chiral Drugs 216

The Chemistry of... Selective Binding of Drug Enantiomers to Left- and Right-Handed Coiled DNA 218

5.12 Molecules with More than One Chirality Center 218

5.13 Fischer Projection Formulas 224

5.14 Stereoisomerism of Cyclic Compounds 226

5.15 Relating Configurations through Reactions in Which No Bonds to the Chirality Center Are Broken 228

5.16 Separation of Enantiomers: Resolution 232

5.17 Compounds with Chirality Centers Other than Carbon 233

5.18 Chiral Molecules that Do Not Possess a Chirality Center 233
6 Nucleophilic Reactions
Properties and Substitution Reactions of Alkyl Halides 240

6.1 Alkyl Halides 241

6.2 Nucleophilic Substitution Reactions 242

6.3 Nucleophiles 244

6.4 Leaving Groups 246

6.5 Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction 246

6.6 A Mechanism for the SN2 Reaction 247

6.7 Transition State Theory: Free-Energy Diagrams 249

6.8 The Stereochemistry of SN2 Reactions 252

6.9 The Reaction of tert-Butyl Chloride with Water: An SN1 Reaction 254

6.10 A Mechanism for the SN1 Reaction 255

6.11 Carbocations 257

6.12 The Stereochemistry of SN1 Reactions 259

6.13 Factors Affecting the Rates of SN1 and SN2 Reactions 262

6.14 Organic Synthesis: Functional Group Transformations Using SN2 Reactions 272

The Chemistry of... Biological Methylation: A Biological Nucleophilic Substitution Reaction 273
7 Alkenes and Alkynes I
Properties and Synthesis. Elimination Reactions of Alkyl Halides 282

7.1 Introduction 283

7.2 The (E )-(Z ) System for Designating Alkene Diastereomers 283

7.3 Relative Stabilities of Alkenes 284

7.4 Cycloalkenes 287

7.5 Synthesis of Alkenes: Elimination Reactions 287

7.6 Dehydrohalogenation 288

7.7 The E2 Reaction 289

7.8 The E1 Reaction 297

7.9 Elimination and Substitution Reactions Compete With Each Other 299

7.10 Elimination of Alcohols: Acid-Catalyzed Dehydration 303

7.11 Carbocation Stability and the Occurrence of Molecular Rearrangements 308

7.12 The Acidity of Terminal Alkynes 312

7.13 Synthesis of Alkynes by Elimination Reactions 313

7.14 Terminal Alkynes Can Be Converted to Nucleophiles for Carbon-Carbon Bond Formation 315

7.15 Hydrogenation of Alkenes 317

The Chemistry of... Hydrogenation in the Food Industry 318

7.16 Hydrogenation: The Function of the Catalyst 319

7.17 Hydrogenation of Alkynes 320

7.18 An Introduction to Organic Synthesis 322

The Chemistry of... From the Inorganic to the Organic 324
8 Alkenes and Alkynes II
Addition Reactions 337

8.1 Addition Reactions of Alkenes 338

8.2 Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov's Rule 340

8.3 Stereochemistry of the Ionic Addition to an Alkene 345

8.4 Addition of Water to Alkenes: Acid-Catalyzed Hydration 346

8.5 Alcohols from Alkenes through Oxymercuration-Demercuration: Markovnikov Addition 349

8.6 Alcohols from Alkenes through Hydroboration-Oxidation: Anti-Markovnikov Syn Hydration 352

8.7 Hydroboration: Synthesis of Alkylboranes 353

8.8 Oxidation and Hydrolysis of Alkylboranes 355

8.9 Summary of Alkene Hydration Methods 358

8.10 Protonolysis of Alkylboranes 359

8.11 Electrophilic Addition of Bromine and Chlorine to Alkenes 359

The Chemistry of... The Sea: A Treasury of Biologically Active Natural Products 362

8.12 Stereospecific Reactions 363

8.13 Halohydrin Formation 364

The Chemistry of... Citrus-Flavored Soft Drinks 366

8.14 Divalent Carbon Compounds: Carbenes 366

8.15 Oxidation of Alkenes: Syn 1,2-Dihydroxylation 368

The Chemistry of... Catalytic Asymmetric Dihydroxylation 370

8.16 Oxidative Cleavage of Alkenes 371

8.17 Electrophilic Addition of Bromine and Chlorine to Alkynes 374

8.18 Addition of Hydrogen Halides to Alkynes 374

8.19 Oxidative Cleavage of Alkynes 375

8.20 How to Plan a Synthesis: Some Approaches and Examples 376
9 Nuclear Magnetic Resonance and Mass Spectrometry
Tools for Structure Determination 391

9.1 Introduction 392

9.2 Nuclear Magnetic Resonance (NMR) Spectroscopy 392

9.3 How To Interpret Proton NMR Spectra 398

9.4 Shielding and Deshielding of Protons: More about Chemical Shift 401

9.5 Chemical Shift Equivalent and Nonequivalent Protons 403

9.6 Spin-Spin Coupling: More about Signal Splitting and Nonequivalent or Equivalent Protons 407

9.7 Proton NMR Spectra and Rate Processes 412

9.8 Carbon-13 NMR Spectroscopy 414

9.9 Two-Dimensional (2D) NMR Techniques 420

The Chemistry of... Magnetic Resonance Imaging in Medicine 423

9.10 An Introduction to Mass Spectrometry 423

9.11 Formation of Ions: Electron Impact Ionization 424

9.12 Depicting the Molecular Ion 424

9.13 Fragmentation 425

9.14 Isotopes in Mass Spectra 432

9.15 GC/MS Analysis 435

9.16 Mass Spectrometry of Biomolecules 436
10 Radical Reactions
10.1 Introduction: How Radicals Form and How They React 449

Hydrogen Atom Abstraction 450

The Chemistry of... Acne Medications 450

10.2 Homolytic Bond Dissociation Energies (DH °) 451

10.3 Reactions of Alkanes with Halogens 454

10.4 Chlorination of Methane: Mechanism of Reaction 456

10.5 Halogenation of Higher Alkanes 459

10.6 The Geometry of Alkyl Radicals 462

10.7 Reactions that Generate Tetrahedral Chirality Centers 462

10.8 Allylic Substitution and Allylic Radicals 466

10.9 Benzylic Substitution and Benzylic Radicals 469

10.10 Radical Addition to Alkenes: The Anti-Markovnikov Addition of Hydrogen Bromide 472

10.11 Radical Polymerization of Alkenes: Chain-Growth Polymers 474

10.12 Other Important Radical Reactions 478

The Chemistry of... Antioxidants 480

The Chemistry of... Ozone Depletion and Chlorofluorocarbons (CFCs) 481
11 Alcohols and Ethers
Synthesis and Reactions 489

11.1 Structure and Nomenclature 490

11.2 Physical Properties of Alcohols and Ethers 492

11.3 Important Alcohols and Ethers 494

The Chemistry of... Ethanol as a Biofuel 495

The Chemistry of... Cholesterol and Heart Disease 496

11.4 Synthesis of Alcohols from Alkenes 496

11.5 Reactions of Alcohols 498

11.6 Alcohols as Acids 500

11.7 Conversion of Alcohols into Alkyl Halides 501

11.8 Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides 501

11.9 Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCl2 504

11.10 Tosylates, Mesylates, and Triflates: Leaving Group Derivatives of Alcohols 505

11.11 Synthesis of Ethers 507

11.12 Reactions of Ethers 513

11.13 Epoxides 514

The Chemistry of... The Sharpless Asymmetric Epoxidation 515

11.14 Reactions of Epoxides 516

11.15 Anti 1,2-Dihydroxylation of Alkenes via Epoxides 519

The Chemistry of... Environmentally Friendly Alkene Oxidation Methods 521

11.16 Crown Ethers 522

The Chemistry of... Transport Antibiotics and Crown Ethers 523

11.17 Summary of Reactions of Alkenes, Alcohols, and Ethers 523
12 Alcohols from Carbonyl Compounds
Oxidation -Reduction and Organometallic Compounds 534

12.1 Structure of the Carbonyl Group 535

12.2 Oxidation-Reduction Reactions in Organic Chemistry 536

12.3 Alcohols by Reduction of Carbonyl Compounds 537

The Chemistry of... Alcohol Dehydrogenase- A Biochemical Hydride Reagent 539

The Chemistry of... Stereoselective Reductions of Carbonyl Groups 541

12.4 Oxidation of Alcohols 542

12.5 Organometallic Compounds 547

12.6 Preparation of Organolithium and Organomagnesium Compounds 548

12.7 Reactions of Organolithium and Organomagnesium Compounds 549

12.8 Alcohols from Grignard Reagents 552

12.9 Protecting Groups 561
13 Conjugated Unsaturated Systems
13.1 Introduction 573

13.2 The Stability of the Allyl Radical 573

13.3 The Allyl Cation 577

13.4 Resonance Theory Revisited 578

13.5 Alkadienes and Polyunsaturated Hydrocarbons 582

13.6 1,3-Butadiene: Electron Delocalization 583

13.7 The Stability of Conjugated Dienes 586

13.8 U ltraviolet-Visible Spectroscopy 587

13.9 Electrophilic Attack on Conjugated Dienes: 1,4-Addition 595

13.10 The Diels-Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes 599

The Chemistry of... Molecules with the Nobel Prize in Their Synthetic Lineage 608
14 Aromatic Compounds
14.1 The Discovery of Benzene 618

14.2 Nomenclature of Benzene Derivatives 619

14.3 Reactions of Benzene 621

14.4 The Kekulé Structure for Benzene 622

14.5 The Thermodynamic Stability of Benzene 623

14.6 Modern Theories of the Structure of Benzene 625

14.7 Hückel's Rule: The 4n + 2 π Electron Rule 628

14.8 Other Aromatic Compounds 636

The Chemistry of... Nanotubes 639

14.9 Heterocyclic Aromatic Compounds 639

14.10 Aromatic Compounds in Biochemistry 641

The Chemistry of... Aryl Halides: Their Uses and Environmental Concerns 643

14.11 Spectroscopy of Aromatic Compounds 644

The Chemistry of... Sunscreens (Catching the Sun's Rays and What Happens to Them) 648
15 Reactions of Aromatic Compounds
15.1 Electrophilic Aromatic Substitution Reactions 661

15.2 A General Mechanism for Electrophilic Aromatic Substitution 662

15.3 Halogenation of Benzene 664

15.4 Nitration of Benzene 665

15.5 Sulfonation of Benzene 666

15.6 Friedel-Crafts Reactions 668

The Chemistry of... Industrial Styrene Synthesis 669

15.7 Synthetic Applications of Friedel-Crafts Acylations: The Clemmensen and Wolff-Kishner Reductions 673

The Chemistry of... DDT 676

15.8 Existing Substituents Direct the Position of Electrophilic Aromatic Substitution 677

15.9 Activating and Deactivating Effects: How Electron-Donating and Electron-Withdrawing Groups Affect the Rate of an EAS Reaction 684

15.10 Directing Effects in Disubstituted Benzenes 685

15.11 Reactions of Benzene Ring Carbon Side Chains 686

15.12 Synthetic Strategies 689

15.13 The SNAr Mechanism: Nucleophilic Aromatic Substitution by Addition-Elimination 691

The Chemistry of... Bacterial Dehalogenation of a PCB Derivative 693

15.14 Benzyne: Nucleophilic Aromatic Substitution by Elimination- Addition 694

The Chemistry of... Host-Guest Trapping of Benzyne 697

15.15 Reduction of Aromatic Compounds 697
16 Aldehydes and Ketones
Nucleophilic Addition to the Carbonyl Group 711

16.1 Introduction 712

16.2 Nomenclature of Aldehydes and Ketones 712

16.3 Physical Properties 714

The Chemistry of... Aldehydes and Ketones in Perfumes 715

16.4 Synthesis of Aldehydes 715

16.5 Synthesis of Ketones 720

16.6 Nucleophilic Addition to the Carbon-Oxygen Double Bond: Mechanistic Themes 723

16.7 The Addition of Alcohols: Hemiacetals and Acetals 726

16.8 The Addition of Primary and Secondary Amines 731

The Chemistry of... A Very Versatile Vitamin, Pyridoxine (Vitamin B6) 735

16.9 The Addition of Hydrogen Cyanide: Cyanohydrins 736

16.10 The Addition of Ylides: The Wittig Reaction 737

16.11 Oxidation of Aldehydes 741

16.12 The Baeyer-Villiger Oxidation 741

16.13 Chemical Analyses for Aldehydes and Ketones 743

16.14 Spectroscopic Properties of Aldehydes and Ketones 743

16.15 Summary of Aldehyde and Ketone Addition Reactions 746
17 Carboxylic Acids and Their Derivatives
Nucleophilic Addition - Elimination at the Acyl Carbon 761

17.1 Introduction 762

17.2 Nomenclature and Physical Properties 762

17.3 Preparation of Carboxylic Acids 770

17.4 Acyl Substitution: Nucleophilic Addition-Elimination at the Acyl Carbon 773

17.5 Acyl Chlorides 775

17.6 Carboxylic Acid Anhydrides 777

17.7 Esters 778

17.8 Amides 784

The Chemistry of... Some Hot Topics Related to Structure and Activity 787

The Chemistry of... Penicillins 792

17.9 Derivatives of Carbonic Acid 792

17.10 Decarboxylation of Carboxylic Acids 795

17.11 Polyesters and Polyamides: Step-Growth Polymers 797

17.12 Summary of the Reactions of Carboxylic Acids and Their Derivatives 798
18 Reactions at the α Carbon of Carbonyl Compounds
Enols and Enolates 811

18.1 The Acidity of the α Hydrogens of Carbonyl Compounds: Enolate Anions 812

18.2 Keto and Enol Tautomers 813

18.3 Reactions via Enols and Enolates 815

The Chemistry of... Chloroform in Drinking Water 819

18.4 Lithium Enolates 821

18.5 Enolates of β-Dicarbonyl Compounds 824

18.6 Synthesis of Methyl Ketones: The Acetoacetic Ester Synthesis 825

18.7 Synthesis of Substituted Acetic Acids: The Malonic Ester Synthesis 830

18.8 Further Reactions of Active Hydrogen Compounds 833

18.9 Synthesis of Enamines: Stork Enamine Reactions 834

18.10 Summary of Enolate Chemistry 837
19 Condensation and Conjugate Addition Reactions of Carbonyl Compounds
More Chemistry of Enolates 849

19.1 Introduction 850

19.2 The Claisen Condensation: A Synthesis of β-Keto Esters 850

19.3 β-Dicarbonyl Compounds by Acylation of Ketone Enolates 855

19.4 Aldol Reactions: Addition of Enolates and Enols to Aldehydes and Ketones 856

The Chemistry of... A Retro-Aldol Reaction in Glycolysis-Dividing Assets to Double the ATP Yield 860

19.5 Crossed Aldol Condensations 861

19.6 Cyclizations via Aldol Condensations 867

The Chemistry of... Polyketide Anticancer Antibiotic Biosynthesis 868

19.7 Additions to α,β-Unsaturated Aldehydes and Ketones 869

The Chemistry of... Conjugate Additions to Activate Drugs 873

19.8 The Mannich Reaction 874

The Chemistry of... A Suicide Enzyme Substrate 875

19.9 Summary of Important Reactions 876
20 Amines
20.1 Nomenclature 891

20.2 Physical Properties and Structure of Amines 892

20.3 Basicity of Amines: Amine Salts 894

The Chemistry of... Biologically Important Amines 899

20.4 Preparation of Amines 901

20.5 Reactions of Amines 909

20.6 Reactions of Amines with Nitrous Acid 911

The Chemistry of... N -Nitrosoamines 912

20.7 Replacement Reactions of Arenediazonium Salts 913

20.8 Coupling Reactions of Arenediazonium Salts 917

20.9 Reactions of Amines with Sulfonyl Chlorides 919

The Chemistry of... Essential Nutrients and Antimetabolites 920

20.10 Synthesis of Sulfa Drugs 921

20.11 Analysis of Amines 921

20.12 Eliminations Involving Ammonium Compounds 923

20.13 Summary of Preparations and Reactions of Amines 924
21 Transition Metal Complexes
Promoters of Key Bond -Forming Reactions 938

21.1 Organometallic Compounds in Previous Chapters 939

21.2 Transition Metal Elements and Complexes 939

21.3 How to Count Electrons in a Metal Complex 940

21.4 Mechanistic Steps in the Reactions of Some Transition Metal Complexes 942

21.5 Homogeneous Hydrogenation: Wilkinson's Catalyst 944

The Chemistry of... Homogeneous Asymmetric Catalytic Hydrogenation: Examples Involving l-DOPA, (S)-Naproxen, and Aspartame 946

21.6 Cross-Coupling Reactions 947

The Chemistry of... The Wacker Oxidation 950

The Chemistry of... Complex Cross Couplings 952

21.7 Olefin Metathesis 955

The Chemistry of... Organic Chemistry Alchemy: Turning Simple Alkenes into "Gold" 957

21.8 Transition Metals in Nature: Vitamin B12 and Vanadium Haloperoxidases 958
22 Carbohydrates
22.1 Introduction 966

22.2 Monosaccharides 968

22.3 Mutarotation 973

22.4 Glycoside Formation 974

22.5 Other Reactions of Monosaccharides 976

22.6 Oxidation Reactions of Monosaccharides 979

22.7 Reduction of Monosaccharides: Alditols 984

22.8 Reactions of Monosaccharides with Phenylhydrazine: Osazones 984

22.9 Synthesis and Degradation of Monosaccharides 986

22.10 The d Family of Aldoses 988

22.11 Fischer's Proof of the Configuration of d-(+)-Glucose 988

22.12 Disaccharides 990

The Chemistry of... Artificial Sweeteners (How Sweet It Is) 993

22.13 Polysaccharides 994

22.14 Other Biologically Important Sugars 998

22.15 Sugars that Contain Nitrogen 999

22.16 Glycolipids and Glycoproteins of the Cell Surface: Cell Recognition and the Immune System 1001

The Chemistry of... Patroling Leukocytes and Sialyl Lewisx Acids 1002

22.17 Carbohydrate Antibiotics 1003

22.18 Summary of Reactions of Carbohydrates 1004
23 Lipids
23.1 Introduction 1012

23.2 Fatty Acids and Triacylglycerols 1012

The Chemistry of... Olestra and Other Fat Substitutes 1016

The Chemistry of... Poison Ivy 1019

The Chemistry of... Self-Assembled Monolayers-Lipids in Materials Science and Bioengineering 1020

23.3 Terpenes and Terpenoids 1021

The Chemistry of... The Bombardier Beetle's Noxious Spray 1025

23.4 Steroids 1026

The Chemistry of... The Enzyme Aromatase 1031

23.5 Prostaglandins 1035

23.6 Phospholipids and Cell Membranes 1036

The Chemistry of... STEALTH® Liposomes for Drug Delivery 1039

23.7 Waxes 1040
24 Amino Acids and Proteins
24.1 Introduction 1046

24.2 Amino Acids 1047

24.3 Synthesis of α-Amino Acids 1053

24.4 Polypeptides and Proteins 1055

24.5 Primary Structure of Polypeptides and Proteins 1058

24.6 Examples of Polypeptide and Protein Primary Structure 1062

The Chemistry of... Sickle-Cell Anemia 1064

24.7 Polypeptide and Protein Synthesis 1065

24.8 Secondary, Tertiary, and Quaternary Structures of Proteins 1071

24.9 Introduction to Enzymes 1075

24.10 Lysozyme: Mode of Action of an Enzyme 1077

The Chemistry of... Carbonic Anhydrase: Shuttling the Protons 1079

24.11 Serine Proteases 1079

24.12 Hemoglobin: A Conjugated Protein 1081

The Chemistry of... Some Catalytic Antibodies 1081

24.13 Purification and Analysis of Polypeptides and Proteins 1083

24.14 Proteomics 1085
25 Nucleic Acids and Protein Synthesis
25.1 Introduction 1091

25.2 Nucleotides and Nucleosides 1092

25.3 Laboratory Synthesis of Nucleosides and Nucleotides 1095

25.4 Deoxyribonucleic Acid: DNA 1098

25.5 RNA and Protein Synthesis 1105

25.6 Determining the Base Sequence of DNA: The Chain-Terminating (Dideoxynucleotide) Method 1113

25.7 Laboratory Synthesis of Oligonucleotides 1116

25.8 Polymerase Chain Reaction 1118

25.9 Sequencing of the Human Genome: An Instruction Book for the Molecules of Life 1120

Glossary GL-1

Index I-1

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The 12th edition of Organic Chemistry continues Solomons, Fryhle Snyders tradition of excellence in teaching and preparing students for success in the organic classroom and beyond. A central theme of the authors approach to organic chemistry is to emphasize the relationship between structure and reactivity.

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Chemistry, 11th Edition [Raymond Chang, Kenneth A. Goldsby] on Amazon.com. *FREE* shipping on qualifying offers. Chemistry, 11th Edition

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A brief introduction to organic chemistry

Carbon can form covalent bonds with itself and other elements to create a mind-boggling array of structures. In organic chemistry, we will learn about the reactions chemists use to synthesize crazy carbon based structures, as well as the analytical methods to characterize them. We will also think about how those reactions are occurring on a molecular level with reaction mechanisms. Simply put, organic chemistry is like building with molecular Legos. Let's make some beautiful organic molecules!

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Organic chemistry | Science | Khan Academy

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