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Course Question & AnswerOrganic Chemistry I
Purpose of Course showclose
Organic chemistry is a branch of chemistry that focuses on a single element: carbon! Carbon bonds strongly with other carbon atoms and with other elements, forming numerous chain and ring structures. As a result, there are millions of distinct carbon compounds known and classified. The vast majority of the molecules that contain carbon are considered organic molecules, with few debatable exceptions such as carbon nanotubes, diamonds, carbonate ions, and carbon dioxide. Carbon is central to the existence of life as it is an essential component of nucleic acids (DNA and RNA), sugars, lipids, and proteins. A well-rounded student of science must take courses in organic chemistry to understand its application to various topics, such as the study of polymers (plastics and other materials), hydrocarbons, pharmaceuticals, molecular biology, biochemistry, and other life sciences.
In the first semester of organic chemistry, you will learn the basic concepts needed to understand the three-dimensional structure of an organic molecule, predict the reactivity of a given molecule (based on its chemical structure), and recognize the mechanisms behind a chemical reaction. You will explore different explanations of how atoms bind in carbon-based molecules and learn about the simplest carbon structures (alkanes) before moving on to more complex carbon structures (alkenes and alkynes) and their reactions.
Learning Outcomes showclose
- Describe organic molecules in terms of bonding, stereochemistry, functional groups, and resonance.
- Demonstrate proficiency in the nomenclature of organic molecules.
- Derive the intermolecular force of given molecules based on their chemical structures.
- Draw and represent organic molecules, using arrow notation to show the movement of electrons.
- Demonstrate proficiency in identifying various classes of reactions (i.e. addition, elimination, arrangements).
- Describe the thermodynamics of organic reactions using energy diagrams.
- Analyze the stereochemistry of simple organic molecules and the stereochemical consequences of reactions.
- Demonstrate proficiency in Newman projections and conformations of cyclohexanes.
- Demonstrate proficiency in determining whether alkyl halides will undergo a substitution or elimination reaction for a given set of reaction conditions.
- Describe the basic reaction mechanisms of alcohols.
- Demonstrate proficiency in calculating the degree of unsaturation of molecules.
- Describe the basic reaction mechanisms of alkenes and alkynes.
- Explain the concept of chirality, optical activity, and stereoisomerism.
- Explain the concept of a carbocation, which is an ion with a positively-charged carbon.
- Rank different carbocations according to their stability and/or reactivity.
- Explain the differences between SN1 and SN2 substitution reactions and between E1 and E2 eliminations reactions.
Course Requirements showclose
√ Have access to a computer.
√ Have continuous broadband internet access.
√ Have the ability/permission to install plug-ins or software (e.g. Adobe Reader or Flash).
√ Have the ability to download and save files and documents to a computer.
√ Have the ability to open Microsoft files and documents (.doc, .ppt,.xls, etc.).
√ Be competent in the English language.
√ Have read the Saylor Student Handbook.
√ Have completed the following courses listed in “The Core Program” of the Chemistry discipline as prerequisites, CHEM001/PHYS101, CHEM002/PHYS102, CHEM003/MA101, CHEM004/MA102, CHEM101 and CHEM102.
Unit Outline show close
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Unit 1: Fundamentals of Organic Chemistry: Chemical Bonding, Intermolecular Forces, and Acids & Bases
This unit introduces organic chemistry. We will start by examining the critical concept of chemical bonds. All bonds are not the same. In fact, according to valence bond theory, many bonds are actually a mix of different atomic orbitals. These bonds are called “hybridized” orbitals; they have different properties and bond angles. Molecular orbital (MO) theory uses the mathematical combinations of atomic orbitals to create molecular orbitals. You will notice that most explanations throughout the course use valence bond theory. Several important concepts necessary to understanding organic chemistry arise from chemical bonding, including chemical structures, molecular shapes and geometries, polarity of chemical bonds (this concept will prove very useful in understanding chemical reactivity later in the course), resonance (later, resonance will explain why a reaction occurs in the manner in which it does), and intermolecular force.
Unit 1 Time Advisory show close
This unit will also review reaction energetics and will teach you how to draw organic molecules and use "arrow notation" to show movements of electrons. It will also cover the concept of isomerism. We will finish up with a discussion of acids and bases within the context of the course.
Unit 1 Learning Outcomes show close
- 1.1 Structure and Bonding
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1.1.1 Review of Bonding, Hybridization, Shape of the Molecules, and Lewis Structures
- Reading: Boise State University: Professor Richard Banks’ “Interactive Inorganic Chemistry Tutorials: Bonding and Hybridization”
Link: Boise State University: Professor Richard Banks’ “Interactive Inorganic Chemistry Tutorials: Bonding and Hybridization” (HTML)
Instructions: Read the entire webpage, and practice drawing the electron-dot structures where indicated.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: University of California, Los Angeles: Department of Chemistry & Biochemistry: Professor Steven A. Hardinger’s “Tutorial on Drawing Lewis Dot Structures”
Link: University of California, Los Angeles: Department of Chemistry & Biochemistry: Professor Steven A. Hardinger’s “Tutorial on Drawing Lewis Dot Structures” (HTML)
Instructions: Read the entire webpage, and practice drawing electron-dot structures.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: kvanderveen's Channel: Dr. V’s AP Chemistry Podcasts by Dr. V: "Lewis Structures, Part 1," "Lewis Structures, Part 2," and "Lewis Structures, Part 3"
Links: YouTube: kvanderveen's Channel: Dr. V’s AP Chemistry Podcasts by Dr. V: "Lewis Structures, Part 1," "Lewis Structures, Part 2," and "Lewis Structures, Part 3" (YouTube)
Instructions: Please watch the three videos to start learning about Lewis Structures. Part 1 and Part 2 are about 9:40 minutes, and Part 3 is about 5 minutes.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: University of Florida: P. J. Brucat’s “Assessments on Drawing Lewis Dot Structures”
Link: University of Florida: P. J. Brucat’s “Assessments on Drawing Lewis Dot Structures” (HTML)
Instructions: The webpage presents a few exercises on drawing Lewis Dot Structures. Follow the written instructions on the webpage to conduct the exercises.
Terms of use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Boise State University: Professor Richard Banks’ “Interactive Inorganic Chemistry Tutorials: Bonding and Hybridization”
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1.1.2 Valence Bond Theory
- Web Media: YouTube: EnderlePhD: University of California, Davis: Brian Enderle’s "Valence Bond Theory”
Link: YouTube: EnderlePhD: University of California, Davis: Brian Enderle’s "Valence Bond Theory” (YouTube)
Instructions: Watch this brief, straightforward explanation of Valence Bond Theory (2:25 minutes).
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Activity: University of Southern Maine: Professor Newton’s “Activity on Valence Bond Theory”
Link: University of Southern Maine: Professor Newton’s “Activity on Valence Bond Theory” (HTML)
Instructions: The webpage presents a few exercises to help the students understand the fundamentals of Valence Bond Theory. Follow the written instructions to conduct the exercises numbered “4,” “5a,” and “5b.”
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “sp3 Hybridized Orbitals and Sigma Bonds” and “Pi bonds and sp2 Hybridized Orbitals”
Link: Khan Academy: Salman Khan’s “sp3 Hybridized Orbitals and Sigma Bonds” and “Pi bonds and sp2 Hybridized Orbitals” (YouTube)
Instructions: Please watch the two videos to reinforce the concepts of bonding and hybridization (30:36 minutes).
Terms of Use: These videos are licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. They are attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Western Oregon University: Dr. Pete Poston's Chemical Bonding II: Molecular Geometry and Hybridization of Atomic Orbitals, Chapter 10: “Electron Pair Geometries in VESPR Theory”
Link: Western Oregon University: Dr. Pete Poston's Chemical Bonding II: Molecular Geometry and Hybridization of Atomic Orbitals, Chapter 10: “Electron Pair Geometries in VESPR Theory” (PDF)
Instructions: Click on the above link and read the entire document to learn about electron pair geometries and VESPR theory.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: Leah4Sci's “Intro to Orgo (4 of 5) Hybrid Orbitals, Bond Angles/Geometry, Molecular Orbitals”
Link: YouTube: Leah4Sci's “Intro to Orgo (4 of 5) Hybrid Orbitals, Bond Angles/Geometry, Molecular Orbitals” (YouTube)
Instructions: Please watch the video in its entirety (15:00).
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: EnderlePhD: University of California, Davis: Brian Enderle’s "Valence Bond Theory”
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1.1.3 Charge Distribution in Molecules: Formal Charge and Polar Covalent Bonds
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Charge Distribution in Molecules"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Charge Distribution in Molecules” (HTML)
Instructions: After reading through the webpage, please select “Formal Charges” from the Practice Problem scroll-down bar and complete the questions.
Terms of Use Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: The McGraw-Hill Companies: Online Learning Center: Carey’s Organic Chemistry, 4e: “Tutorial on How to Calculate Formal Charges”
Link: The McGraw-Hill Companies: Online Learning Center: Carey’s Organic Chemistry, 4e: “Tutorial on How to Calculate Formal Charges” (HTML)
Instructions: Read the entire webpage, and click on the "Examples" links.
Terms of Use Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: EducatorVids: Professor Harold Goldwhite’s “Covalent Bonds and Polar Bonds"
Link: YouTube: EducatorVids: Professor Harold Goldwhite’s “Covalent Bonds and Polar Bonds" (YouTube)
Instructions: Please watch the video in its entirety (7:19 minutes).
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: You Tube: FreeOnlineCollege’s "IE Organic Lecture 1.2 (New) - Formal Charge & Lewis Examples"
Link: You Tube: FreeOnlineCollege’s "IE Organic Lecture 1.2 (New) - Formal Charge & Lewis Examples" (YouTube)
Instructions: Please watch the video in its entirety (9:31 minutes).
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: ClarkCollegeTWC: Tutor Joey Smokey’s "Molecular Shape"
Link: YouTube: ClarkCollegeTWC: Tutor Joey Smokey’s "Molecular Shape" (YouTube)
Instructions: Please watch the entire 5-minute video.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Charge Distribution in Molecules"
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1.1.4 Resonance Structures
- Reading: University of California, Los Angeles: Professor Steven A. Hardinger’s “Resonance: Drawing Resonance Structures” and Pennsylvania State University: Professor P. Maslak’s “Rules for Writing Resonance Structures”
Links: University of California, Los Angeles: Professor Steven A. Hardinger’s “Resonance: Drawing Resonance Structures” (HTML) and Pennsylvania State University: Professor P. Maslak’s “Rules for Writing Resonance Structures” (HTML)
Instructions: Click the first link, which will take you to a webpage that illustrates the step-by-step procedure for understanding and drawing the resonance structures of organic molecules. The second text can be viewed on Professor Maslak’s webpage. Please click on the “Quantum Primer” link and then on the “Resonance” link to be directed to the information titled “8. Resonance Structures.” When you have completed the readings, try the practice problems under “Exercises” (molecules “A” through “H”) found at the end of the University of California, Los Angeles link. Then, check your answers by clicking on the link at the very end of the page.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Web Media: YouTube: Freelance Teacher’s "How to Draw Resonance Structures"
Link: YouTube: Freelance Teacher’s "How to Draw Resonance Structures” (YouTube)
Instructions: This is the link to the first video of a series of lectures on drawing resonance structures. There are about 50 of these videos from the same instructor.
Please watch video #1 to begin to learn about resonance structures (8:30 minutes).
Optional: On the right column of the YouTube page under "suggestions," you can find the link to the remaining videos on this topic produced by the Freelanceteacher. You can watch videos 2-50 for an in-depth explanation of resonance structures in organic chemistry.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Activity: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Resonance: Drawing Resonance Structures”
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Resonance: Drawing Resonance Structures” (HTML)
Instructions: The webpage presents a few exercises on drawing Resonance Structures from the Virtual Textbook of Organic Chemistry. Follow the written instructions to conduct the exercises.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: University of California, Los Angeles: Professor Steven A. Hardinger’s “Resonance: Drawing Resonance Structures” and Pennsylvania State University: Professor P. Maslak’s “Rules for Writing Resonance Structures”
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1.1.5 Drawing Organic Molecules
- Web Media: Khan Academy: Salman Khan’s “Representing Structures of Organic Molecules”
Link: Khan Academy: Salman Khan’s “Representing Structures of Organic Molecules” (YouTube)
Instructions: Please watch the video in its entirety (7:29 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Web Media: YouTube: Dr. Enderle’s "Chemistry and Stuff by Dr. E: Drawing Organics"
Link: YouTube: Dr. Enderle’s "Chemistry and Stuff by Dr. E: Drawing Organics" (YouTube)
Instructions: Please watch this brief 3-minute video.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Practice in Drawing Structural Formulas,” “Identifying Line Formulas,” and “Structure Matching”
Links: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Practice in Drawing Structural Formulas,” (JAVA) “Identifying Line Formulas,” (JAVA) and “Structure Matching” (HTML)
Instructions: Practice drawing organic molecules using these interactive exercises from the Virtual Textbook of Organic Chemistry. Follow the instructions on each webpage to complete the exercises.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Representing Structures of Organic Molecules”
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1.1.6 Introduction to Isomerism
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Isomers"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Isomers” (HTML)
Instructions: Read an introduction to isomers. Isomers will be studied in detail in the following units. After reading through the webpage, please select “Identifying Line Formulas” and “Formulas: Line and Condensed” from the Practice Problem scroll-down bar and complete the questions.
Terms of Use Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Isomers"
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1.1.7 Atomic and Molecular Orbitals
- Reading: Imperial College: “Introduction to Molecular Orbital Theory” and MIT: Lecture Handouts: “Review of Molecular Orbital Theory, Hybridization/LCAO”
Links: Imperial College: “Introduction to Molecular Orbital Theory” (HTML) and MIT: Lecture Handouts: “Review of Molecular Orbital Theory, Hybridization/LCAO” (PDF)
Instructions: Read through both documents. The first from Imperial College is a webpage that summarizes the Molecular Orbital theory. From the second link, please click on the “PDF” hyperlink listed after “Lecture 3” to open and read the entirety of the PDF file, which reviews the molecular orbital theory and hybridization.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Imperial College: “Introduction to Molecular Orbital Theory” and MIT: Lecture Handouts: “Review of Molecular Orbital Theory, Hybridization/LCAO”
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1.2 Intermolecular Forces
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Intermolecular Forces"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Intermolecular Forces" (HTML)
Instructions: Read the entire webpage. The last section of this webpage contains a scroll down menu listing three different problem topics. Practice all the problems linked here. This reading covers subunits 1.2.1 through 1.2.5.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Intermolecular Forces"
- 1.2.1 Boiling and Melting Points
- 1.2.2 Hydrogen Bonding
- 1.2.3 Crystalline Solids
- 1.2.4 Water Solubility
- 1.2.5 Intermolecular Forces and Physical Properties
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1.3 Reaction Energetics
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Energetics"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Energetics" (HTML)
Instructions: Read the entire webpage. Recall from general chemistry that reactions only occur if they are energetically favorable. The same is true for organic reactions. Energy diagrams are useful for explaining why a reaction occurs in the manner that it does in terms of energy. Here, we will discuss the energetics of organic reaction before introducing reactivity of organic molecules in Unit 3. We will review the concept of spontaneity as well as exothermic and endothermic reactions. This reading covers subunits 1.3.1 through 1.3.4.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Lecture: YouTube: UCITLTC: University of California, Irvine: Dr. James Nowick’s “Energetics of Reactions”
Link: YouTube: UCITLTC: University of California, Irvine: Dr. James Nowick’s “Energetics of Reactions” (YouTube)
Instructions: Watch this video (36:421 minutes) to learn the basics on the energetics of reactions. This resource covers subunits 1.3.1 through 1.3.4.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Energetics"
- 1.3.1 Exothermic Reactions
- 1.3.2 Endothermic Reactions
- 1.3.3 Activation Energy
- 1.3.4 Transition States
- 1.4 Acids and Bases in Organic Chemistry
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1.4.1 Bronsted and Lowry Acids and Bases
- Reading: University of Texas, Austin: Professor Nathan L. Bauld’s "Bronsted Acids and Bases in Organic Chemistry"
Link: University of Texas, Austin: Professor Nathan L. Bauld’s "Bronsted Acids and Bases in Organic Chemistry" (HTML)
Instructions: Read the tutorial webpage. This resource covers subunits 1.4.1.1 through 1.4.1.2.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: Clark College Tutoring and Writing Center: Tutor Kevin Martin’s "Acid and Base Strength"
Link: YouTube: Clark College Tutoring and Writing Center: Tutor Kevin Martin’s "Acid and Base Strength" (YouTube)
Instructions: Please watch the entire video (4:16 minutes). This resource covers subunits 1.4.1.1 through 1.4.1.2.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: University of Texas, Austin: Professor Nathan L. Bauld’s "Bronsted Acids and Bases in Organic Chemistry"
- 1.4.1.1 Definition of Acids and Bases According to Bronsted and Lowry
- 1.4.1.2 Factors that Determine the Strength of Acids and Bases
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1.4.2 Lewis Acid and Bases
- Reading: University of California, Davis: UC Davis ChemWiki: "Lewis Concept of Acids and Bases"
Link: University of California, Davis: UC Davis ChemWiki: "Lewis Concept of Acids and Bases" (HTML or PDF)
Instructions: Read the tutorial webpage, and complete the practice problems. Note that in organic chemistry, acids and bases are described as electron donors (Lewis bases) and electron acceptors (Lewis acids). In subsequent units, Lewis acids and bases are linked to electrophiles and nucleophiles (these two concepts will be explained in subunit 2.4).
Note: You can view this as a PDF by clicking the “Make PDF” button at the top of the linked webpage.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Lecture: YouTube: UCITLTC: University of California, Irvine: Professor James Nowick’s "Lewis Acids, Lewis Bases, and Organic Reaction Mechanisms”
Link: YouTube: UCITLTC: University of California, Irvine: Professor James Nowick’s "Lewis Acids, Lewis Bases, and Organic Reaction Mechanisms” (YouTube)
Instructions: Please watch the first 13 minutes of the video lecture linked above.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: University of California, Davis: UC Davis ChemWiki: "Lewis Concept of Acids and Bases"
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Unit 2: Overview of Organic Chemistry: Functional Groups and Classes of Chemical Reactions
Here you will learn the basic concepts necessary to understanding the rest of the course. Each of these concepts will be mastered in the appropriate units ahead, but a general overview is necessary at this point.
Unit 2 Time Advisory show close
In this unit, you will learn how to classify organic molecules based on their functional group(s). A functional group is a group of atoms that presents characteristic physical and chemical properties, such as chemical reactivity or spectroscopy behavior. You will also learn how to use arrow notation to indicate movements of electrons in organic reactions. The unit will conclude with an introduction to organic reactions and an explanation of how to classify a reaction based on a particular technique or reagent.
Unit 2 Learning Outcomes show close
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2.1 Functional Groups
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Characteristic Reactions of Functional Groups”
Links: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Characteristic Reactions of Functional Groups” (HTML)
Instructions: Review the definition of ‘functional group’ at the top of the page. Then, study all of the functional class (column one) and the corresponding formula (column two).
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: Tutor Vista: "Functional Groups in Organic Compounds”
Link: YouTube: Tutor Vista: "Functional Groups in Organic Compounds" (YouTube)
Instructions: Watch this short video to visualize how organic molecules with different functionalities can be generated from the same alkyl residue.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s “Identifying Functional Groups I” and “Identifying Functional Groups II"
Links: Michigan State University: Professor William Reusch’s "Identifying Functional Groups I” (HTML) and “Identifying Functional Groups II" (HTML)
Instructions: Practice identifying functional groups using these interactive exercises from the Virtual Textbook of Organic Chemistry. Follow the instructions on each webpage to answer the questions.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Characteristic Reactions of Functional Groups”
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2.2 Curved Arrow Notation
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Curved Arrow Notation"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Curved Arrow Notation" (HTML)
Instructions: Read the section titled “The Arrow Notation in Mechanisms.”
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s “Evaluating Curved Mechanism 1” and “Evaluating Curved Mechanism 2"
Links: Michigan State University: Professor William Reusch’s "Evaluating Curved Arrow Mechanisms 1” (HTML) and “Evaluating Curved Arrow Mechanisms 2" (HTML)
Instructions: Practice the curved arrow notations using these interactive exercises from the Virtual Textbook of Organic Chemistry. Follow the instructions on each webpage to complete the assessment.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Curved Arrow Notation"
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2.3 Overview of Chemical Reactivity
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Chemical Reactivity"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Chemical Reactivity" (HTML)
Instructions: Read the sections titled “Chemical Reactivity,” “Reaction Classification,” “Reaction Variables,” and “Reactive Intermediates.” This resource also covers the topics outlined in subunits 2.3.1 and 2.3.2.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Chemical Reactivity"
- 2.3.1 Reaction Variables
- 2.3.2 Reactive Intermediates
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2.4 Introduction to Organic Reactions
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Examples of Organic Reactions”
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Examples of Organic Reactions” (HTML)
Instructions: Read the section titled “Examples of Organic Reactions.” This material also covers subunit 2.4.1.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Nucleophilicity and Basicity”
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Nucleophilicity and Basicity” (HTML)
Instructions: Read the section titled “Nucleophilicity and Basicity Factors in Organic Reactions.” This material also covers the topics outlined in subunits 2.4.1 through 2.4.3.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s “Classifying Chemical Reactions,” “Identify the Electrophile,” and “Identify the Nucleophile”
Links: Michigan State University: Professor William Reusch’s "Classifying Chemical Reactions,” (HTML) “Identify the Electrophile,” (HTML) and “Identify the Nucleophile” (HTML)
Instructions: Practice the classification of chemical reactions using these interactive exercises from the Virtual Textbook of Organic Chemistry. This resource also covers the topics outlined in subunits 2.4.1 through 2.4.3.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Examples of Organic Reactions”
- 2.4.1 Example of Organic Reactions (Addition, Elimination, Substitution, Radicals, Rearrangements)
- 2.4.2 Definition of Electrophiles (Positively Polarized Atoms)
- 2.4.3 Definition of Nucleophiles (Negatively Polarized Atoms)
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Unit 3: Alkanes
We will now transition into looking at each family of organic molecules, noting their respective properties and reactivity. All units covering functional groups are structured into two main parts: 1) Nomenclature, Structural, and Physical Properties; and 2) Reactivity. In the first section, we will study molecular nomenclature, or the systematic naming of molecules as defined by the International Union of Pure and Applied Chemistry (IUPAC). In many ways, organic chemistry is analogous to learning a foreign language. We must learn how to describe structures in the language that organic chemists use.
Unit 3 Time Advisory show close
We will start with the simplest hydrocarbons: the alkanes. Alkanes are hydrocarbons with only carbon and hydrogens. In addition to nomenclature and properties, this unit will cover the concept of isomerism in detail. Isomerism is the study of many different structures that molecules with same chemical formula can have. The unit will conclude with a section on the reactivity of alkanes. Alkanes are often described as non-reactive, inert, or low-reactive compounds. However, under drastic conditions, these molecules can react and yield many of the molecules and materials we encounter in our daily life, including the major components in gasoline.
Unit 3 Learning Outcomes show close
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3.1 Nomenclature of Alkanes and Cycloalkanes
- Web Media: Khan Academy: Salman Khan’s “Naming Simple Alkanes”; Naming Alkanes with Alkyl Groups”; “Correction – 2-Propylheptane should never be the name!”; “Common and Systematic Naming – Iso, Sec, and Tert Prefixes”; “Organic Chemistry Naming Examples 1”; “Organic Chemistry Naming Examples 2”; “Organic Chemistry Naming Examples 3”; “Organic Chemistry Naming Examples 4”; “Organic Chemistry Naming Examples 5
Link: Khan Academy: Salman Khan’s “Naming Simple Alkanes” (YouTube); Naming Alkanes with Alkyl Groups” (YouTube); “Correction – 2-Propylheptane should never be the name!” (YouTube); “Common and Systematic Naming – Iso, Sec, and Tert Prefixes” (YouTube); “Organic Chemistry Naming Examples 1” (YouTube); “Organic Chemistry Naming Examples 2” (YouTube); “Organic Chemistry Naming Examples 3” (YouTube); “Organic Chemistry Naming Examples 4” (YouTube); “Organic Chemistry Naming Examples 5” (YouTube)
Instructions: Please watch the nine videos to reinforce the reading material (82:28 minutes). Several examples are worked to help familiarize you with the naming methods.
Terms of Use: These resources are licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. They are attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Michigan State University: Department of Chemistry: Professor William Reusch’s “Nomenclature”
Link: Michigan State University: Department of Chemistry: Professor William Reusch’s “Nomenclature” (HTML)
Instructions: Read the sections titled “Naming Organic Compounds,” “Alkanes,” and “Cycloalkanes.” Click on the various links on this webpage to see additional examples. At the end of the cycloalkane section, there is a scroll down menu with link to several “Practice Problems.” Please select the first question and do the exercises.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Lecture: YouTube: University of California, Irvine: Professor James Nowick’s “Nomenclature of Alkanes, Conformations of Ethane”
Link: YouTube: University of California, Irvine: Professor James Nowick’s “Nomenclature of Alkanes, Conformations of Ethane” (YouTube)
Instructions: Please watch the first 20 minutes of this lecture.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Naming Simple Alkanes”; Naming Alkanes with Alkyl Groups”; “Correction – 2-Propylheptane should never be the name!”; “Common and Systematic Naming – Iso, Sec, and Tert Prefixes”; “Organic Chemistry Naming Examples 1”; “Organic Chemistry Naming Examples 2”; “Organic Chemistry Naming Examples 3”; “Organic Chemistry Naming Examples 4”; “Organic Chemistry Naming Examples 5
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3.2 Stereoisomers of Linear Alkanes
- Reading: University of British Columbia: Professor W. Stephen McNeil’s “Conformations of Alkanes” and Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: Stereoisomers
Links: University of British Columbia: Professor W. Stephen McNeil’s “Conformations of Alkanes” (HTML) and Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Stereoisomers” (HTML)
Instructions: For the first link, read the sections titled “Stereoisomers,” “Conformational Isomers,” “Ethane Conformations,” and “Butane Conformations.” Read the entirety of the Michigan State University webpage. These resources also cover subunits 3.2.2 and 3.2.3.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Web Media: YouTube: Far From Standard Tutoring: John Hennessy’s “Newman Projections"
Link: YouTube: Far From Standard Tutoring: John Hennessy’s “Newman Projections" (YouTube)
Instructions: Please watch the entire video (about 8 minutes). This resource also covers subunit 3.2.1.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Lecture: YouTube: University of California, Irvine: Professor James Nowick’s “Nomenclature of Alkanes, Conformations of Ethane”
Link: YouTube: University of California, Irvine: Professor James Nowick’s “Nomenclature of Alkanes, Conformations of Ethane” (YouTube)
Instructions: Having already watched the first 20 minutes of this lecture in subunit 3.1, please now watch the last 30 minutes. This resource covers the topics outlined in subunits 3.2.2 through 3.2.3.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Distinguishing Different Formulas” and “Identifying Conformer Representations”
Links: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Distinguishing Different Formulas” (HTML) and “Identifying Conformer Representations” (HTML)
Instructions: Focus only on linear molecules. Practice drawing alkanes and their stereoisomers using these interactive exercises from the Virtual Textbook of Organic Chemistry. Please follow the directions on each webpage to complete the assessment. This resource covers topics outlined in subunits 3.2.1 through 3.2.3.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: University of British Columbia: Professor W. Stephen McNeil’s “Conformations of Alkanes” and Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: Stereoisomers
- 3.2.1 Newman Projections
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3.2.2 Conformational Isomers
- Web Media: Khan Academy: Salman Khan’s “Newman Projections”
Link: Khan Academy: Salman Khan’s “Newman Projections” (YouTube)
Instructions: Please watch the video, which demonstrates how Newman projections arise (14:22 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Newman Projections”
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3.2.3 Examples of Ethane and Butane
- Web Media: Khan Academy: Salman Khan’s “Newman Projections 2”
Link: Khan Academy: Salman Khan’s “Newman Projections 2” (YouTube)
Instructions: Please watch the video, which demonstrates how to draw Newman projections for ethane and butane (11:12 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Newman Projections 2”
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3.3 Isomers of Cycloalkanes
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Cycloalkane Configurational Isomers,” “Ring Conformations,” “Cycloalkanes,” and “Substituted Cyclohexanes"
Links: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Cycloalkane Configurational Isomers,” (HTML) “Ring Conformations,” (HTML) “Cycloalkanes,” (HTML) and “Substituted Cyclohexanes" (HTML)
Instructions: Read the sections linked above. In the previous unit, we learned about the different conformations an alkane can assume upon free rotation along a carbon-carbon bond. In cycloalkanes, this free rotation is not permitted as atoms are "locked" in a ring structure. These rings are not as rigid as they might appear. In fact, cycloalkanes often undergo "ring flip." In this section, you will learn about this flipping phenomena, the stable configuration of cycloalkanes (called "chair"), the less stable one (called "boat"), and the energy barrier to be overcome for ring flipping.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s “Distinguishing Different Formulas,” “Identifying Conformer Representations,” “Conformational Analysis,” and “Identifying Gauche Interactions”
Links: Michigan State University: Professor William Reusch’s “Distinguishing Different Formulas,” (HTML) “Identifying Conformer Representations,” (HTML) “Conformational Analysis,” (HTML) and “Identifying Gauche Interactions” (HTML)
Instructions: Focus only on the cyclic molecules. Practice drawing cycloalkanes and their stereoisomers using these interactive exercises from the Virtual Textbook of Organic Chemistry. Follow the instructions at the top of each webpage to complete the assessment.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Chair and Boat Shapes for Cyclohexane” and “Double Newman Diagram for Methylcyclohexane”
Link: Khan Academy: Salman Khan’s “Chair and Boat Shapes for Cyclohexane” (YouTube) and “Double Newman Diagram for Methylcyclohexane” (YouTube)
Instructions: Please watch the two videos to reinforce the material covered in the reading assignment (27:07 minutes).
Terms of Use: These resources are licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. They are attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Cycloalkane Configurational Isomers,” “Ring Conformations,” “Cycloalkanes,” and “Substituted Cyclohexanes"
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3.4 Drawing Chair Conformations of Cyclohexanes
- Reading: University of California, Davis: UC Davis ChemWiki: "Ring Strain and the Structure of Cycloalkanes”
Link: University of California, Davis: UC Davis ChemWiki: "Ring Strain and the Structure of Cycloalkanes." (HTML or PDF)
Instructions: Read the tutorial webpage, and complete the practice problems.
Note: You can view this as a PDF by clicking the “Make PDF” button near the top of the linked webpage.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Lecture: YouTube: UCITLTC: University of California, Irvine: Professor James Nowick’s “Conformations of Cyclohexane”
Link: YouTube: UCITLTC: University of California, Irvine: Professor James Nowick’s “Conformations of Cyclohexane” (YouTube)
Instructions: Please watch the video (36:58 minutes) to understand the conformations of cyclohexane.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: University of California, Davis: UC Davis ChemWiki: "Ring Strain and the Structure of Cycloalkanes”
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3.5 Reactivity
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alkanes"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alkanes" (HTML)
Instructions: Read the entire webpage about the reactivity of alkanes. At the bottom of the page, from the Practice Problems scroll-down menu, select and complete the “Halogenations of Alkanes” problems. This resource covers subunits 3.5.1 through 3.5.2.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Web Media: YouTube: mfmayer’s “Introduction to Halogenation of Alkanes” and YouTube: jamesmungall's Channel: James Mungall Chemistry Tutorials by James Mungall: "Radical Substitution - Chlorination of Methane”
Links: YouTube: mfmayer’s “Introduction to Halogenation of Alkanes” (YouTube) and YouTube: jamesmungall's Channel: James Mungall Chemistry Tutorials by James Mungall: “Radical substitution - Chlorination of Methane” (YouTube)
Instructions: Please watch these brief videos (3-5 minutes each) to understand the reactivity of alkanes. This resource also covers subunit 3.5.2.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alkanes"
- 3.5.1 Combustion
- 3.5.2 Halogenation
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Unit 4: Alkyl Halides
The alkyl halide is the first class of reactive molecules you will encounter in your organic chemistry course (as you may recall, alkanes are generally considered low reactive molecules). Alkyl halides are halogen-substituted alkanes, which are also known as haloalkanes or halogenoalkanes. The characteristic functional group is the carbon-halogen bond (recall that fluorine, chlorine, bromine, and iodine are the four halogens). The most widely used alkyl halides are probably the CFCs (chlorofluorocarbons), which are used as refrigerants in home refrigerators and car air conditioning systems. Alkyl halides are also found in flame-retardants and fire extinguishers and used as solvents (dichloromethane, chloroform, etc.) and reagents in organic synthesis. After learning the nomenclature, structural, and physical properties of alkyl halides, you will discover two classes of chemical reactions: the nucleophilic substitution (SN) and the nucleophilic elimination (E). These classes are typical of the carbon-halogen bond and they occur following two distinct reaction mechanisms: unimolecular (SN1 or E1) or bimolecular (SN2 and E2). In this unit, you will learn how to predict the mechanism (and therefore the reaction products) by evaluating the nature and structure of the alkyl halides, the strength of the nucleophile, and reaction conditions. This unit also introduces the concepts of chirality, stereocenters, and optical activity. Understanding how to synthesize molecules with the desired chiral centers is critical to the pharmaceutical industry.
Unit 4 Time Advisory show close
Unit 4 Learning Outcomes show close
- 4.1 Nomenclature, Structural and Physical Properties
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4.1.1 Nomenclature of Alkyl Halides
- Web Media: Khan Academy: Organic Chemistry: "Naming Alkyl Halides"
Link: Khan Academy: Salman Khan’s “Naming Alkyl Halides” (YouTube)
Instructions: Please watch the video, which explains how alkyl halides are named using the IUPAC system (9:03 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Web Media: Khan Academy: Organic Chemistry: "Naming Alkyl Halides"
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4.1.2 Occurrence of Halides
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Occurrence of Alkyl Halides"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Occurrence of Alkyl Halides" (HTML)
Instructions: Read this unit to know the natural occurrence of alkyl halides.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Occurrence of Alkyl Halides"
- 4.1.3 Stereoisomers
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4.1.3.1 Chiral Centers
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Stereoisomer Part II"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Stereoisomers Part II” (HTML)
Instructions: Read the sections titled “Chirality & Symmetry,” “Enantiomorphism,” and “Optical Activity.” This resource also covers the topics outlined in subunits 4.1.3.1.1 through 4.1.3.1.3.
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Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Introduction to Chirality”; “Chiral Examples 1”; and “Chiral Examples 2”
Link: Khan Academy: Salman Khan’s: "Introduction to Chirality” (YouTube); “Chiral Example 1” (YouTube); and “Chiral Example 2” (YouTube)
Instructions: Please watch these three videos, which introduce chirality and demonstrate how to determine chiral conformations (28:07 minutes).
Terms of Use: These resources are licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. They are attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Stereoisomer Part II"
- 4.1.3.1.1 Chirality and Symmetry Elements
- 4.1.3.1.2 Enantiomorphism
- 4.1.3.1.3 Optical Activity
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4.1.3.2 Chiral Configurations
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Chiral Configurations"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: Chiral Configurations” (HTML)
Instructions: Read the entire chapter on this webpage. Focus on these specific topics: “Designating the Configuration for Chiral Centers,” “Compounds with Two or More Chiral Centers,” “Fischer Projection Formulas,” “Achiral Diastereomers (meso Compounds),” “Other Configurational Notations,” “Resolution of Racemates,” and “Conformational Enantiomorphism.” This resource also covers the topics outlined in subunits 4.1.3.2.1 through 4.1.3.2.9.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Cahn-Ingold-Prelog System for Naming Enantiomers” and “R,S (Cahn-Ingold-Prelog) Naming Example 2”
Link: Khan Academy: Salman Khan’s: “Cahn-Ingold-Prelog System for Naming Enantiomers” (YouTube) and “R,S (Cahn-Ingold-Prelog) Naming Example 2” (YouTube)
Instructions: Please watch these two videos, which explain the nomenclature of enantiomers (22:10 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Web Media: YouTube: Your Formula Sheet: “Fischer Projection”
Link: YouTube: Your Formula Sheet: “Fischer Projection” (YouTube)
Instructions: Please watch the entire video (2:42 minutes). This resource covers subunits 4.1.3.2.1 through 4.1.3.2.9.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Stereoisomers: Practice Problems”
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Stereoisomers: Practice Problems” (HTML)
Instructions: Select a problem from the Practice Problems scroll-down menu. Practice on all problems. This resource covers the topics in subunits 4.1.3.2.1 through 4.1.3.2.9.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Chiral Configurations"
- 4.1.3.2.1 Chiral Configurations
- 4.1.3.2.2 Configurational Nomenclature
- 4.1.3.2.3 Compounds with Several Stereogenic Centers
- 4.1.3.2.4 Stereogenic Nitrogen
- 4.1.3.2.5 Fischer Projection Formulas
- 4.1.3.2.6 Achiral Diastereomers
- 4.1.3.2.7 Other Configurational Notations
- 4.1.3.2.8 Resolution
- 4.1.3.2.9 Conformational Enantiomorphism
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4.1.4 Summary of Isomerism
- Web Media: Khan Academy: Salman Khan’s “Stereoisomers, Enantiomers, Diastereomers, Constitutional Isomers and Meso Compunds”
Link: Khan Academy: Salman Khan’s: “Stereoisomers, Enantiomers, Diastereomers, Constitutional Isomers and Meso Compunds” (YouTube)
Instructions: Please watch the videos, which discuss different isomer configurations (13:36 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Isomer Summary"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Isomer Summary" (HTML)
Instructions: Please read the entire webpage for a review of the different types of isomerism.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Stereoisomers, Enantiomers, Diastereomers, Constitutional Isomers and Meso Compunds”
- 4.2 Reactivity of Alkyl Halides: Substitution and Elimination of the "Halide"
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4.2.1 Carbocations (Positively Charged Carbons)
- Reading: Chemguide: Jim Clark’s “Carbocations”
Link: Chemguide: Jim Clark’s “Carbocations” (HTML)
Instructions: Read the entire webpage. This resource covers subunits 4.2.1.1 through 4.2.1.2.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Chemguide: Jim Clark’s “Carbocations”
- 4.2.1.1 Relative Strengths of Carbocations
- 4.2.1.2 Carbocation Rearrangements
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4.2.2 Affecting Substitution and Elimination Reactions
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alkyl Halide Reactions"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alkyl Halide Reactions" (HTML)
Instructions: Read the entire section titled "Alkyl Halide Reactions."
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alkyl Halide Reactions"
-
4.2.3 Nucleophilic Substitutions: SN2 and SN1 Mechanisms
- Reading: Chemguide: Jim Clark’s “Nucleophilic Substitution”
Link: Chemguide: Jim Clark’s “Nucleophilic Substitution” (HTML)
Instructions: Read the entire webpage. This resource also covers the topics outlined in subunits 4.2.3.1 through 4.2.3.8.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Mechanisms of Nucleophilic Substitution Reactions"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Mechanisms of Nucleophilic Substitution Reactions" (HTML)
Instructions: Read the entire webpage, and practice with the reactions at the end of the section titled “2. The SN1 Mechanism.” This resource covers the topics outlined in subunits 4.2.3.1 through 4.2.3.8.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: ValChemistry’s "SN1 Mechanism and Examples" and "SN2 Mechanism and Examples"
Links: YouTube: ValChemistry’s "SN1 Mechanism and Examples" (YouTube) and "SN2 Mechanism and Examples" (YouTube)
Instructions: Watch these tutorial videos on nucleophilic substitutions (about 7 minutes for the first video and about 4 minutes for the second video). This resource covers subunits 4.2.3.1 through 4.2.3.8.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Sn2 Reactions”; “Sn1 Reactions”; “Steric Hindrance”; “Sn2 Stereochemistry”; “Solvent Effects on Sn1 and Sn2 Reactions”; “Nucleophilicity (Nuecleophile Strength)”; and “Nucleophilicity vs. Basicity”
Link: Khan Academy: Salman Khan’s: “Sn2 Reactions” (YouTube); “Sn1 Reactions” (YouTube); “Steric Hindrance” (YouTube); “Sn2 Stereochemistry” (YouTube); “Solvent Effects on Sn1 and Sn2 Reactions” (YouTube); “Nucleophilicity (Nucleophile Strength)” (YouTube); and “Nucleophilicity vs. Basicity” (YouTube)
Instructions: Please watch these seven videos, which describe SN1 and SN2 reaction mechanisms and their conditions (84:51 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Chemguide: Jim Clark’s “Nucleophilic Substitution”
- 4.2.3.1 Rate Law of SN2 (Bimolecular)
- 4.2.3.2 Mechanism of SN2 (One-Step, Concerted Mechanism)
- 4.2.3.3 Stereochemistry of SN2 (Inversion of Stereochemistry)
- 4.2.3.4 Conditions Favoring SN2 (Less Substituted carbons, Non-polar Aprotic Solvent)
- 4.2.3.5 Rate Law of SN1 (Unimolecular; Rate-Dependent on Only Substrate)
- 4.2.3.6 Mechanism of SN1 (Two-Step Mechanism)
- 4.2.3.7 Stereochemistry of SN1 (Racemic)
- 4.2.3.8 Conditions Favoring SN1 (More Substituted Carbons, Allylic and Benzylic Carbons, Polar Protic Solvent)
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4.2.4 Elimination Reactions: E2 and E1 Mechanisms
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Elimination Reactions of Alkyl Halides"Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Elimination Reactions of Alkyl Halides" (HTML)Instructions: Read the entire webpage to learn about elimination reactions. This resource covers subunits 4.2.4.1 through 4.2.4.6.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Chemguide: Jim Clark’s “Elimination from Unsymmetric Halogenoalkanes”
Link: Chemguide: Jim Clark’s “Elimination from Unsymmetric Halogenoalkanes” (HTML)
Instructions: Read the entire webpage. This resource covers subunits 4.2.4.1 through 4.2.4.6.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy’s "E1 Reactions" and "E2 Reactions"
Link: Khan Academy’s "E1 Reactions" (YouTube) and "E2 Reactions" (YouTube)
Instructions: Watch both videos in their entirety; each video lecture is about 9 minutes. This resource covers subunits 4.2.4.1 through 4.2.4.6.
Terms of Use: These resources are licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. They are attributed to the Khan Academy.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “E2 Reactions”; “E1 Reactions”; and “Zaitsev’s Rule”
Link: Khan Academy: Salman Khan’s: “E2 Reactions” (YouTube); “E1 Reactions” (YouTube); and “Zaitsev’s Rule” (YouTube)
Instructions: Please watch these three videos, which describe E1 and E2 reaction mechanisms and how to predict the products based on Zaitsev’s rule (31:44 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Elimination Reactions of Alkyl Halides"
- 4.2.4.1 Rate Law of E2 (Bimolecular)
- 4.2.4.2 Mechanism of E2 (One-Step, Concerted Mechanism)
- 4.2.4.3 Conditions favoring E2 (Strong Base)
- 4.2.4.4 No Geometrical Preference (E1)
- 4.2.4.5 Mechanism of E1 (Two-Step Mechanism)
- 4.2.4.6 Conditions Favoring E1 (Weak Base)
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4.2.5 Summary of Substitution vs. Elimination
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Summary of Substitution vs. Elimination"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Summary of Substitution vs. Elimination" (HTML)
Instructions: Use this table as a guide to determine under which conditions a particular reagent may undergo nucleophilic substitution or elimination. Note, however, that there might be exceptions to these rules of thumb.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Comparing E2 E1 Sn2 Sn1 Reactions”; “E2 E1 Sn2 Sn1 Reactions Example 2”; and “E2 E1 Sn2 Sn1 Reactions Example 3”
Link: Khan Academy: Salman Khan’s: “Comparing E2 E1 Sn2 Sn1 Reactions” (YouTube); “E2 E1 Sn2 Sn1 Reactions Example 2” (YouTube); and “E2 E1 Sn2 Sn1 Reactions Example 3” (YouTube)
Instructions: Please watch these three videos, which provide demonstrations of nucleophilic substitution and elimination reaction mechanisms (28:50 minutes).
Terms of Use: These resources are licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. They are attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Summary of Substitution vs. Elimination"
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4.2.6 Reactions of Alkyl Halides with Reducing Metals: Grignard and Alkyl Lithium Reagents
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alkyl Halide Reactivity"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alkyl Halide Reactivity" (HTML)
Instructions: Read the entire webpage, “Organometallic Compounds” through “Reactions of Dihalides.” This resource covers the topics outlined in subunits 4.2.6.1 through 4.2.6.3.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: ChemProfessor98's Channel: "Orgo Chem-Grignard Reaction"
Link: YouTube: ChemProfessor98's Channel: "Orgo Chem-Grignard Reaction" (YouTube)
Instructions: Watch this tutorial video about the Grignard Reaction (7:46 minutes). This resource covers subunits 4.2.6.1 through 4.2.6.3.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alkyl Halide Reactivity: Practice Problems"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alkyl Halide Reactivity: Practice Problems" (HTML)
Instructions: Use the Practice Problems scroll-down menu to select, and complete all the problems. This resource covers topics outlined in subunits 4.2.6.1 through 4.2.6.3.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alkyl Halide Reactivity"
- 4.2.6.1 Grignard reagents
- 4.2.6.2 Alkyl lithium
- 4.2.6.3 Elimination Reactions of Dihalides
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Unit 5: Alcohols
Alcohols are characterized by the presence of a hydroxyl group bound to a carbon (C-OH) in the molecular structure. This is the first family of organic molecules with strong intramolecular forces (hydrogen bonds) you have encountered so far. Most of the alcohols' physical properties are determined by these forces, such as their relatively high boiling point and high solubility in water. Simple alcohols are produced in industrial quantities because they find applications in the food and beverage industry (ethanol), cosmetics (ethanol, and isopropanol), antifreezes and cooling systems (methanol), cleaning products, and, more recently, gasoline (where ethanol and butanol are used as additives). In this unit, you will learn how to name and synthesize alcohols. You will also read about alcohol’s most common reactions and learn how to use these reactions to convert alcohols into more valuable products.
Unit 5 Time Advisory show close
Unit 5 Learning Outcomes show close
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5.1 Nomenclature
- Web Media: Khan Academy: Salman Khan’s “Alcohols”
Link: Khan Academy: Salman Khan’s: “Alcohols” (YouTube)
Instructions: Please watch the video to reinforce material covered in the reading (6:50 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alcohol Nomenclature"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Alcohol Nomenclature" (HTML)
Instructions: Read the section titled "Alcohol Nomenclature."
Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above.See a broken link? Please let us know!
- Web Media: YouTube: Freelanceteacher’s “Tutorial on Alcohol Nomenclature”
Link: YouTube: Freelanceteacher’s “Tutorial on Alcohol Nomenclature" (YouTube)
Instructions: Watch this video lecture in its entirety (10:46 minutes).
Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Alcohols”
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5.2 Acidity of Alcohol
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alcohol"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alcohol" (HTML)
Instructions: Read the section titled “Alcohol Reactions.” Then, click the link just below the section on “Alcohol Reactions” for a discussion of “Molecular Structure and Acidity.”
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alcohol"
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5.3 Synthesis and Reactions of Alcohols
- Reading: University of California, Davis: UC Davis ChemWiki: "Electrophilic Hydration to Make Alcohols”
Link: University of California, Davis: UC Davis ChemWiki: "Electrophilic Hydration to Make Alcohols" (HTML or PDF)
Instructions: Read the tutorial webpage, and complete the practice problems. This resource also covers subunit 5.3.1. You can view this in a PDF version by clicking the “Make PDF” button at the top of the linked webpage.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alcohols”
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alcohols” (HTML)
Instructions: Read the entire chapter on alcohol reactions. Click on the link titled “Oxidation Reactions of Alcohols and Reactions of Phenols” at the bottom of the webpage to continue reading on this topic. Skip the section titled “Phenols.” After the Phenol section, you will find some useful practice problems related to alcohols. From the scroll-down menu, choose the problem topic to test your knowledge of alcohols. This resource also covers the topics outlined in subunits 5.3.2-5.3.7.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above.See a broken link? Please let us know!
- Web Media: YouTube: Mark Rosengarten’s "Chemistry Tutorial 13.3a: Organic Families: Alcohols"
Link: YouTube: Mark Rosengarten’s "Chemistry Tutorial 13.3a: Organic Families: Alcohols" (YouTube)
Instructions: Please watch this 8-minute video in its entirety. This video provides a short overview of alcohols. This resource covers subunits 5.3.1-5.3.7.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above.See a broken link? Please let us know!
- Web Media: YouTube: Freelanceteacher’s "Organic Chemistry: Alcohols (1)"
Link: YouTube: Freelanceteacher’s "Organic Chemistry: Alcohols (1)" (YouTube)
Instructions: Watch this video #1 to start learning about alcohols (about 9:30 minutes). On the right column of the YouTube page under "suggestions," you can find the link to the remaining videos produced by Freelanceteacher. You may choose to watch all the 12 videos for an in-depth explanation of the chemistry of alcohols, although this is not required. This resource covers subunits 5.3.1-5.3.7.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above.See a broken link? Please let us know!
- Reading: University of California, Davis: UC Davis ChemWiki: "Electrophilic Hydration to Make Alcohols”
- 5.3.1 Synthesis of Alcohols via Electrophilic Hydration
- 5.3.2 Substitution of the Hydroxyl H
- 5.3.3 Substitution of the Hydroxyl Group
- 5.3.4 Elimination of Water (Dehydration of Alcohols)
- 5.3.5 Oxidation of Alcohols
- 5.3.6 Conversion of Alcohols into Alkyl Halides and Tosylates
- 5.3.7 Alcohol’s Reaction with Trimethyl Silane
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Unit 6: Alkenes
Alkenes are hydrocarbons with carbon-carbon double bonds. Alkenes are also known as ‘olefins’ which means ‘oil forming gas’. Many important alkenes are found in plants and animals as well as in industrial compounds. ‘Ethylene’, for example, is the largest-volume organic compound produced. The alkene reactions you will learn about here will serve as the basis for understanding the more complex reactions you will encounter later in the course and in more advanced courses, such as pharmaceutical and medicinal chemistry. You should make sure you understand the rationale and mechanisms behind the reactions listed prior to moving on, as they are extremely important!
Unit 6 Time Advisory show close
Unit 6 Learning Outcomes show close
- 6.1 Nomenclature, Structural and Physical Properties
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6.1.1 Alkene Nomenclature
- Web Media: Khan Academy: Salman Khan’s “Naming Alkenes Examples”
Link: Khan Academy: Salman Khan’s: “Naming Alkenes Examples” (YouTube)
Instructions: Please watch the video about the nomenclature of alkenes (8:27 minutes).
Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. It is attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Nomenclature of Alkenes” and “Nomenclature of Alkene Stereoisomers"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Nomenclature of Alkenes” (HTML) and “Nomenclature of Alkene Stereoisomers" (HTML)
Instructions: Read these webpages to learn how to name alkenes.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Web Media: YouTube: ChemII Pickens’ “Naming Alkenes Part 1” and “Naming Alkenes Part 2”
Links: YouTube: ChemII Pickens’ “Naming Alkenes Part 1” (YouTube) and “Naming Alkenes Part 2” (YouTube)
Instructions: Watch these two videos (8-10 minutes each) to understand alkenes nomenclature.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Drawing and Naming Alkene Stereoisomers”
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Drawing and Naming Alkene Stereoisomers” (HTML)
Instructions: In the short section titled "Practice Problems," there is a scroll down menu with several problem topics. Select "Drawing and Naming Alkene Stereoisomers,” and practice on all problems.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Naming Alkenes Examples”
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6.1.2 Alkene Configurational Isomers
- Reading: University of Texas: Professor Nathan L. Bauld’s “Alkenes I: Properties of Alkenes”
Link: University of Texas: Professor Nathan L. Bauld’s “Alkenes I: Properties of Alkenes” (HTML)
Instructions: From the table of contents, select and read “Cis/Trans Isomerism in Alkenes” and “E,Z System of Alkene Nomenclature.” This resource also covers the topics outlined in subunits 6.1.2.1 through 6.1.2.2.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Web Media: YouTube: ChemII Pickens’ “Cis and Trans Isomers in Alkenes”
Link: YouTube: ChemII Pickens’ “Cis and Trans Isomers in Alkenes” (YouTube)
Instructions: Watch the 5-minute video to understand cis- and trans-isomerism. This resource also covers subunits 6.1.2.1 through 6.1.2.2.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Assessment: Elmhurst College, Illinois: Virtual Chembook: “Cis-Trans Isomers of Alkenes”
Link: Elmhurst College, Illinois: Virtual Chembook: “Cis-Trans Isomers of Alkenes” (HTML)
Instructions: Read the webpage and complete the quiz at the bottom of the page (note that you can check your answers). This resource covers subunits 6.1.2.1 through 6.1.2.2.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Cis-Trans and E,Z Naming Scheme for Alkenes” and “Entgegen-Zusammen Naming Scheme for Alkenes Examples”
Link: Khan Academy: Salman Khan’s: “Cis-Trans and E,Z Naming Scheme for Alkenes” (YouTube) and “Entgegen-Zusammen Naming Scheme for Alkenes Examples” (YouTube)
Instructions: Please watch these two videos, which explain the cis-trans and E,Z nomenclature of alkenes (11:00 minutes).
Terms of Use: These resources are licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. Thy are attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: University of Texas: Professor Nathan L. Bauld’s “Alkenes I: Properties of Alkenes”
- 6.1.2.1 Cis/trans isomerism
- 6.1.2.2 E/Z notation
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6.1.3 Degree of Unsaturation
- Reading: University of California, Davis: UC Davis ChemWiki: "Degree of Unsaturation"
Link: University of California, Davis: UC Davis ChemWiki: "Degree of Unsaturation” (HTML or PDF)
Instructions: Read the webpage, and complete the practice problems located toward the end of the page. Note that calculating the degree of unsaturation is important when you elucidate the structure of a molecule, derive and draw a molecule from its chemical formula, and later deduce the structure of a molecule from the spectroscopy data.
Note: You can view this in a PDF by clicking the “Make PDF” button near the top of the linked webpage.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: EnderlePhD’s “Degree of Unsaturation”
Link: YouTube: EnderlePhD’s “Degree of Unsaturation” (YouTube)
Instructions: Watch the video (10 minutes) to understand how to calculate the degree of unsaturation.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: University of California, Davis: UC Davis ChemWiki: "Degree of Unsaturation"
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6.2 Synthesis and Reactivity
- Reading: University of California, Davis: UC Davis ChemWiki: "Alkenes"
Link: University of California, Davis: UC Davis ChemWiki: "Alkenes” (HTML or PDF)
Instructions: In the table of contents, select the following reactions and read the corresponding material: “Alkenes by Dehydration of Alcohols,” “Catalytic Hydrogenation of Alkenes,” “Catalytic Hydrogenation of Alkenes: Relative Stability of Double Bonds,” “Diazomethane, Carbenes, and Cyclopropane Synthesis,” “Electrophilic Addition of Halogens to Alkenes,” “Electrophilic Addition of Hydrogen Halides,” “Hydroboration Oxidation,” “Oxacyclopropane Synthesis,” “Ozonolysis,” “Radical Additions: Anti-Markovnikov Product Formation,” “Radical Allylic Halogenation,” and “Vicinal Syn Dihydroxylation.” This resource also covers the topics outlined in subunits 6.2.1 through 6.2.12.
Note: These are all available as a PDF by clicking the “Make PDF” button near the top of each page.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: Khan Academy: Salman Khan’s “Introduction to Reaction Mechanisms”; “Markovnikov’s Rule and Carbocations”; “Addition of Water (Acid-Catalyzed) Mechanism”; and “Polymerization of Alkenes with Acid”
Link: Khan Academy: Salman Khan’s: “Introduction to Reaction Mechanisms” (YouTube) and “Markovnikov’s Rule and Carbocations” (YouTube); “Addition of Water (Acid-Catalyzed) Mechanism” (YouTube); and “Polymerization of Alkenes with Acid” (YouTube)
Instructions: Please watch these four videos, which describe some of the reaction mechanisms involving alkenes (45:56 minutes).
Terms of Use: These resources are licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. They are attributed to the Khan Academy.See a broken link? Please let us know!
- Reading: University of California, Davis: UC Davis ChemWiki: "Alkenes"
- 6.2.1 Alkene Synthesis by Dehydration of Alcohols
- 6.2.2 Catalytic Hydrogenation of Alkenes
- 6.2.3 Catalytic Hydrogenation of Alkenes: Relative Stability of Double Bonds
- 6.2.4 Diazomethane, Carbenes, and Cyclopropane Synthesis
- 6.2.5 Electrophilic Addition of Halogens to Alkenes
- 6.2.6 Electrophilic Addition of Hydrogen Halides
- 6.2.7 Hydroboration Oxidation
- 6.2.8 Oxacyclopropane Synthesis
- 6.2.9 Ozonolysis
- 6.2.10 Radical Additions: Anti-Markovnikov Product Formation
- 6.2.11 Radical Allylic Halogenation
- 6.2.12 Vicinal Syn Dihydroxylation
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6.2.13 Addition Reactions of Alkenes Part I
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Addition Reactions of Alkenes Part I,” “Addition Reactions of Alkenes Part II,” and “Free Radical Reactions of Alkenes”
Links: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Addition Reactions of Alkenes Part I,” (HTML) “Addition Reactions of Alkenes Part II,” (HTML) and “Free Radical Reactions of Alkenes” (HTML)
Instructions: Read the entirety of these three sections, taken from the Virtual Textbook of Organic Chemistry, which discuss alkenes’ reactivity. This resource covers subunits 6.2.13 through 6.2.15.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Web Media: YouTube: ChemII Pickens’ “Reactions of Alkenes”
Link: YouTube: ChemII Pickens’ “Reactions of Alkenes” (YouTube)
Instructions: Watch the brief 9-minute video that summarizes the most common reactions of alkenes. This resource covers subunits 6.2.13 through 6.2.15.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alkenes Part II: Practice Problems”
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alkenes Part II: Practice Problems” (HTML)
Instructions: Select and complete all the problems from the scroll-down menu. These problems are taken from the Virtual Textbook of Organic Chemistry. This resource covers subunits 6.2.13 through 6.2.15.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Addition Reactions of Alkenes Part I,” “Addition Reactions of Alkenes Part II,” and “Free Radical Reactions of Alkenes”
- 6.2.14 Addition Reactions of Alkenes Part II
- 6.2.15 Free Radical Reactions of Alkenes
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Unit 7: Alkynes
In this unit, you will learn about alkynes, which are molecules characterized by a triple carbon-carbon bond. This particular bond confers unique reactivity to alkynes, such as the capability of forming stable salts with alkaline metal.
Unit 7 Time Advisory show close
Unit 7 Learning Outcomes show close
- 7.1 Nomenclature, Structural and Physical Properties
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7.1.1 Nomenclature of Alkynes
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Nomenclature: IUPAC Rules for Alkyne Nomenclature"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Nomenclature: IUPAC Rules for Alkyne Nomenclature” (HTML)
Instructions: Read the box “IUPAC Rules for Alkyne Nomenclature.” Examples can be found by following the link just below the box. Look at the examples in the Illustrations 6 and 7.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Nomenclature: IUPAC Rules for Alkyne Nomenclature"
-
7.1.2 Properties of Alkynes
- Reading: University of California, Davis: UC Davis ChemWiki: "Properties and Bonding in the Alkynes"
Link: University of California, Davis: UC Davis ChemWiki: "Properties and Bonding in the Alkynes” (HTML or PDF)
Instructions: Read the entire webpage.
Note: You can view this as a PDF by clicking the “Make PDF” button near the top of the linked webpage.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: University of California, Davis: UC Davis ChemWiki: "Properties and Bonding in the Alkynes"
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7.2 Synthesis and Reactivity of Alkynes
- Reading: University of California, Davis: UC Davis ChemWiki: "Alkynes"
Link: University of California, Davis: UC Davis ChemWiki: "Alkynes” (HTML or PDF)
Instructions: In the table of contents, select the following reactions and review the corresponding webpage: “Preparation of Alkynes from Alkynyl Anions” and “Preparation of Alkynes by Double Elimination.” Click the first link and read the linked PPT file for a presentation on the preparation of alkynes from alkynyl anions. Then, click the second link. This will take you to a webpage that reviews the synthesis of alkynes by double elimination. Go through the readings under links 1 through 4. When you have completed the readings, try the practice problems, under “In the Lab.” Then, check your answers by clicking on the “Answers” link. This resource covers subunits 7.2.1 through 7.2.2.
Note: Each page is available as a PDF by clicking the “Make PDF” button near the top of the page.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above.See a broken link? Please let us know!
- Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reaction of Alkynes"
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reaction of Alkynes" (HTML)
Instructions: Read this webpage in its entirety. This resource covers subunits 7.2.1 through 7.2.10.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Web Media: YouTube: Freelanceteacher’s “Alkyne Synthesis and Reactions”
Link: YouTube: Freelanceteacher’s “Alkyne Synthesis and Reactions" (YouTube)
Instructions: Watch this video #1 to start learning about alkynes. On the right column of the YouTube page under "suggestions," you can find the link to the remaining videos on this topic produced by the Freelanceteacher. You can watch videos 1-10 for an in-depth lecture on alkynes. This resource covers subunits 7.2.1 through 7.2.10.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alkynes: Practice Problem”
Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alkynes: Practice Problems” (HTML)
Instructions: Select and complete all the problems from the scroll-down menu. This resource covers the topics outlined in subunits 7.2.1 through 7.2.10.
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.See a broken link? Please let us know!
- Reading: University of California, Davis: UC Davis ChemWiki: "Alkynes"
- 7.2.1 Preparation of Alkynes from Alkynyl Anions
- 7.2.2 Preparation of Alkynes by Double Elimination
- 7.2.3 Electrophilic Addition Reactions
- 7.2.4 Hydrogenation
- 7.2.5 Hydration and Tautomerism
- 7.2.6 Hydroboration
- 7.2.7 Nucleophilic Addition & Reduction
- 7.2.8 Oxidative Cleavage
- 7.2.9 Acidity of Alkynes and the Acetylide Anion
- 7.2.10 Carbon-Carbon Bond Formation Using Acetylide Anions
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Final Exam
- Final Exam: The Saylor Foundation's CHEM103 Final Exam
Link: The Saylor Foundation's CHEM103 Final Exam (HTML and Java)
Instructions: You must be logged into your Saylor Foundation School account in order to access this exam. If you do not yet have an account, you will be able to create one, free of charge, after clicking the link.See a broken link? Please let us know!
- Final Exam: The Saylor Foundation's CHEM103 Final Exam
