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CHEM103: Organic Chemistry I

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. 

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 Time Advisory
This unit will take approximately 27.75 hours to complete.

☐    Subunit 1.1: 12.75 hours
☐    Sub-subunit 1.1.1: 2 hours

☐    Sub-subunit 1.1.2: 2.5 hours

☐    Sub-subunit 1.1.3: 1.5 hours

☐    Sub-subunit 1.1.4: 2.5 hours

☐    Sub-subunit 1.1.5: 1.25 hours

☐    Sub-subunit 1.1.6: 1.5 hours

☐    Sub-subunit 1.1.7: 1.5 hours

☐    Subunit 1.2: 5 hours
☐    Sub-subunit 1.2.1: 1.0 hour

☐    Sub-subunit 1.2.2: 1.5 hours

☐    Sub-subunit 1.2.3: 0.5 hour

☐    Sub-subunit 1.2.4: 1.5 hours

☐    Sub-subunit 1.2.5: 0.5 hour    

☐    Subunit 1.3: 5 hours
☐    Sub-subunit 1.3.1: 1 hour

☐    Sub-subunit 1.3.2: 1 hour

☐    Sub-subunit 1.3.3: 1 hour

☐    Sub-subunit 1.3.4: 2 hours

☐    Subunit 1.4: 5 hours
☐    Sub-subunit 1.4.1: 3 hours

☐    Sub-subunit 1.4.2: 2 hours

Unit1 Learning Outcomes
Upon successful completion of this unit, the student will be able to:

  • Describe chemical bonding using valence bond theory and molecular orbital theory.
  • Draw Lewis structures, assign molecular geometries, and calculate formal charges.
  • Explain the concept of resonance.
  • Draw organic molecules.
  • Evaluate the strength of intermolecular forces.
  • Describe reaction energetics.
  • Identify and evaluate the strength of acids and bases used in organic chemistry.

1.1 Structure and Bonding   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.  
    
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displayed on the webpage above.
  • 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.

  • 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.   
     
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  • 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.
     
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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).
 
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  • 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.”
     
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  • 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” (HTML)

    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.

  • 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.

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  • 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).

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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.
 
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  • 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.
     
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  • 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).
     
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  • 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).
     
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  • 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.
     
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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.
 
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  • 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.
     
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  • 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.
     
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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” (HTML)
 
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.

  • 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.
     
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  • 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.

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.
 
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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. The MIT lecture is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States license.

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.
 
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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   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.
 
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  • 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.
     
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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   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.
 
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  • 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.
     
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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   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.
 
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  • 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.
     
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