Student Solutions Manual for Organic Chemistry

Description

Prepared by Jan William Simek, this manual provides detailed solutions to all in-chapter as well as end-of-chapter exercises in the text.

About the Book

Organic Chemistry offers the following features to facilitate learning:

Highly refined presentation and features present key principles of organic chemistry in the context of fundamental reasoning and problem solving.

• Expanded coverage of Acid/Base Chemistry in Chapter 2 and separation of the material on Substitution and Elimination into two distinct chapters allow students to build upon their existing knowledge and move through their first mechanisms with greater clarity and with more opportunities to test and apply their understanding without getting overwhelmed.
• Problem Solving Strategies have been added and explicitly highlighted in each chapter, including new strategies for resonance, acid-base equilibria, and multistep synthesis.
• Green chemistry is emphasized with presentation of less-toxic, environmentally friendly reagents in many situations, such as oxidation of alcohols with bleach rather than with chromium reagents.
• Chapter Openers focus on applications discussed in the chapter, with introductions and images for a more enticing, contemporary presentation.
• Reaction Starbursts appear before the end of chapter material of every ‘reaction-based chapter’ to help students better understand and mentally organize reactive similarities and distinctions.
• NEW! Visual Guides to Organic Reactions place the reactions covered in major chapters within the overall context of the reactions covered in the course.
• New! Over 100 new problems include more synthesis problems and problems based on recent literature.
• UPDATED! Art has been revised throughout to provide consistency and clarity in the text, giving students access to detailed representations of molecular and orbital art.

 

Also available as a Pearson eText or packaged with Mastering Chemistry

 

Pearson eText is a simple-to-use, mobile-optimized, personalized reading experience that can be adopted on its own as the main course material. It lets students highlight, take notes, and review key vocabulary all in one place, even when offline. Seamlessly integrated videos and other rich media engage students and give them access to the help they need, when they need it. Educators can easily share their own notes with students so they see the connection between their eText and what they learn in class – motivating them to keep reading, and keep learning. Learn more about Pearson eText.

MasteringChemistry is the leading online homework, tutorial, and assessment system, designed to improve results by engaging students before, during, and after class with powerful content. Instructors ensure students arrive ready to learn by assigning educationally effective content before class, and encourage critical thinking and retention with in-class resources such as Learning Catalytics^™. Students can further master concepts after class through traditional and adaptive homework assignments that provide hints and answer-specific feedback. The Mastering gradebook records scores for all automatically graded assignments in one place, while diagnostic tools give instructors access to rich data to assess student understanding and misconceptions.

 

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

 

Before Class

• Dynamic Study Modules help students study effectively on their own by continuously assessing their activity and performance in real time. Here’s how it works: students complete a set of questions with a unique answer format that also asks them to indicate their confidence level. Questions repeat until the student can answer them all correctly and confidently. Once completed, Dynamic Study Modules explain the concept using materials from the text. These are available as graded assignments prior to class, and accessible on smartphones, tablets, and computers. Organic Chemistry Dynamic Study Modules focus on general chemistry remediation, acid-base chemistry, functional groups, nomenclature, and key mechanisms
• Pearson eText is a simple-to-use, mobile-optimized, personalized reading experience available within Mastering. It lets students easily highlight, take notes, and review key vocabulary all in one place – even when offline. Seamlessly integrated videos and other rich media engage students and give them access to the help they need, when they need it.

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

After Class

• 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.

 

1. Structure and Bonding

2. Acids and Bases: Functional Groups

3. Structure and Stereochemistry of Alkanes

4. The Study of Chemical Reactions

5. Stereochemistry

6. Alkyl Halides. Nucleophilic Substitution

7. Structure and Synthesis of Alkenes; Elimination

8: Reactions of Alkenes

9. Alkynes

10. Structure and Synthesis of Alcohols

11. Reactions of Alcohols

12. Infrared Spectroscopy and Mass Spectrometry

13. Nuclear Magnetic Resonance Spectroscopy

14. Ethers, Epoxides and Thioethers

15. Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

16. Aromatic Compounds

17. Reactions of Aromatic Compounds

18. Ketones and Aldehydes

19. Amines

20. Carboxylic Acids

21. Carboxylic Acid Derivatives

22. Condensations and Alpha Substitutions of Carbonyl Compounds

23. Carbohydrates and Nucleic Acids

24. Amino Acids, Peptides, and Proteins

25. Lipids

26. Polymers

About our authors

L.G. “Skip” Wade received his B.A. from Rice in 1969 and then went on to Harvard University, where he did research with Professor James D. White. While at Harvard, he served as the Head Teaching Fellow for the organic laboratories and was strongly influenced by the teaching methods of two master educators, Professors Leonard K. Nash and Frank H. Westheimer. After completing his Ph.D. at Harvard in 1974, Dr. Wade joined the chemistry faculty at Colorado State University. Over the course of fifteen years at Colorado State, Dr. Wade taught organic chemistry to thousands of students working toward careers in all areas of biology, chemistry, human medicine, veterinary medicine, and environmental studies. He also authored research papers in organic synthesis and in chemical education, as well as eleven books reviewing current research in organic synthesis. Since 1989, Dr. Wade has been a chemistry professor at Whitman College, where he teaches organic chemistry and pursues interests in organic synthesis and forensic chemistry. Dr. Wade received the A.E. Lange Award for Distinguished Science Teaching at Whitman in 1993.

Jan Simek was born to humble coal-mining parents who taught him to appreciate the importance of carbon at a very early age. At age 14, he was inspired to pursue a career teaching chemistry by his high school chemistry teacher, Joe Plaskas. Under the guidance of Professor Kurt Kaufman at Kalamazoo College, Dr. Simek began lab work in synthesis of natural products that turned into research in hop extracts for the Kalamazoo Spice Extraction Company. After receiving a master’s degree from Stanford University, Dr. Simek worked in the pharmaceutical industry, synthesizing compounds designed to control diabetes and atherosclerosis, and assisted in the isolation of anti-cancer antibiotics from natural sources. Returning to Stanford University, Dr. Simek completed his Ph.D. with the legendary Professor Carl Djerassi, who developed the first synthesis of steroidal oral contraceptives.

Dr. Simek’s 35-year teaching career was spent primarily at California Polytechnic State University, San Luis Obispo, where he received the university’s Distinguished Teaching Award. Other teaching experiences include Albion College, the University of Colorado at Boulder, Kalamazoo College, and the University of California at Berkeley. In addition to his pharmaceutical research, he has industrial experience investigating dyes, surfactants, and liquid crystals, and he continues to consult for the biotechnology industry.

Although his outside interests include free climbing in Yosemite, performing in a reggae band, and parasailing over the Pacific, as close as he gets to any of those is tending his backyard garden with his wife Judy.

About the Book

Organic Chemistry offers the following features to facilitate learning:

Highly refined presentation and features present key principles of organic chemistry in the context of fundamental reasoning and problem solving.

• New! Expanded coverage of Acid/Base Chemistry in Chapter 2 and separation of the material on Substitution and Elimination into two distinct chapters allow students to build upon their existing knowledge and move through their first mechanisms with greater clarity and with more opportunities to test and apply their understanding without getting overwhelmed.
• NEW! Problem Solving Strategies have been added and explicitly highlighted in each chapter, including new strategies for resonance, acid-base equilibria, and multistep synthesis.
• NEW! Green chemistry is emphasized with presentation of less-toxic, environmentally friendly reagents in many situations, such as oxidation of alcohols with bleach rather than with chromium reagents.
• NEW! Chapter Openers focus on applications discussed in the chapter, with introductions and images for a more enticing, contemporary presentation.
• NEW! Reaction Starbursts appear before the end of chapter material of every ‘reaction-based chapter’ to help students better understand and mentally organize reactive similarities and distinctions.
• NEW! Visual Guides to Organic Reactions place the reactions covered in major chapters within the overall context of the reactions covered in the course.
• NEW! Over 100 new problems include more synthesis problems and problems based on recent literature.
• 20 Key Mechanism boxes highlight the fundamental mechanistic principles that recur throughout the course and are the basis for some of the longer, more complex mechanisms. Each describes the steps of the reaction in detail with a specific example to reinforce the mechanism and a concluding problem to help students absorb these essential reactions.
• Over 50 Mechanism boxes help students understand how specific reactions occur by zooming in on each individual step in detail.
• UPDATED! Art has been revised throughout to provide consistency and clarity in the text, giving students access to detailed representations of molecular and orbital art.

• Essential Problem Solving Skills help students navigate problems and key topics in the text.

Also available as a Pearson eText or packaged with Mastering Chemistry

 

Pearson eText is a simple-to-use, mobile-optimized, personalized reading experience that can be adopted on its own as the main course material. It lets students highlight, take notes, and review key vocabulary all in one place, even when offline. Seamlessly integrated videos and other rich media engage students and give them access to the help they need, when they need it. Educators can easily share their own notes with students so they see the connection between their eText and what they learn in class — motivating them to keep reading, and keep learning. Learn more about Pearson eText.

MasteringChemistry is the leading online homework, tutorial, and assessment system, designed to improve results by engaging students before, during, and after class with powerful content. Instructors ensure students arrive ready to learn by assigning educationally effective content before class, and encourage critical thinking and retention with in-class resources such as Learning Catalytics^™. Students can further master concepts after class through traditional and adaptive homework assignments that provide hints and answer-specific feedback. The Mastering gradebook records scores for all automatically graded assignments in one place, while diagnostic tools give instructors access to rich data to assess student understanding and misconceptions.

 

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

 

Before Class

• NEW! Dynamic Study Modules help students study effectively on their own by continuously assessing their activity and performance in real time. Here’s how it works: students complete a set of questions with a unique answer format that also asks them to indicate their confidence level. Questions repeat until the student can answer them all correctly and confidently. Once completed, Dynamic Study Modules explain the concept using materials from the text. These are available as graded assignments prior to class, and accessible on smartphones, tablets, and computers. Organic Chemistry Dynamic Study Modules focus on general chemistry remediation, acid-base chemistry, functional groups, nomenclature, and key mechanisms
• NEW! Pearson eText is a simple-to-use, mobile-optimized, personalized reading experience available within Mastering. It lets students easily highlight, take notes, and review key vocabulary all in one place — even when offline. Seamlessly integrated videos and other rich media engage students and give them access to the help they need, when they need it.

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 your students develop critical thinking skills
  • Monitor responses to find out where students are struggling
  • Use real-time data to adjust your instructional strategy and try other ways of engaging your students  during class
  • Manage student interactions by automatically grouping students for discussion, teamwork, and peer-to-peer learning
• NEW! Six NMR/IR Spectroscopy simulations (a partnership with Advanced Chemistry Dynamic labs) allow professors and students access to limitless spectral analysis with guided activities that can be used in lab, in the classroom, of after class to study and explore spectra virtually. Activities authored by Mike Huggins, Univ of West Florida, prompt students to utilize the spectral simulator and walks them through different analysis and possible conclusions to draw from the spectra.  

 

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.

• 120 Organic Chemistry-specific tutorials built around the most challenging topics in Organic Chemistry provide 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.
• Enhanced end-of-chapter problems now include wrong-answer specific feedback on all mechanism problems so students have a greater opportunity to practice and understand organic chemistry, without being unnecessarily distracted by the formatting details of using the drawing tool.

 

Prepared by Jan William Simek, this manual provides detailed solutions to all in-chapter as well as end-of-chapter exercises in the text.