Course Syllabus for "CHEM201: Advanced Organic Chemistry".

Remember that organic chemistry is the discipline that studies the properties and reactions of organic, carbon-based compounds.  This course is intended to be taken after the first two semesters of organic chemistry.  Many of the topics within this outline have been covered in the first two semesters of organic chemistry; however, this course will explore these topics in much greater depth.  It is important to make sure that you have a good grasp of the concepts from earlier organic chemistry courses before moving on to this course. We begin by studying a unit on ylides, benzyne, and free radicals.  Many free radicals affect life processes.  For example, oxygen-derived radicals may be overproduced in cells, such as white blood cells that try to defend against infection in a living organism.  In the first unit, you will learn about free radicals, including oxygen-containing compounds.  Afterward we move into a comprehensive examination of stereochemistry, as well as the kinetics of substitution and elimination reactions.  After learning the information in that unit, you will be able to describe reaction mechanisms.  The course wraps up with a final unit, which is a survey of various hetereocyclic structures, including their MO theory, aromaticity, and reactivity.

Learning Outcomes

Upon successful completion of this course, you will be able to:

Course Requirements

In order to take this course, you must:
 
√    Have access to a computer.

√    Have a basic understanding of computers.

√    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: CHEM101: General Chemistry I, CHEM102: General Chemistry II, CHEM103: Organic Chemistry I, CHEM104: Organic Chemistry II

Course Information

Welcome to CHEM 201.  Below, please find general information on this course and its requirements.  

Course Designer: Rachel Lerebours

Primary Resources: This course is composed of a range of free online materials.  However, the course primarily makes use of the following materials:

Requirements for Completion: In order to complete this course, you will need to work through each unit and all of its assigned materials.  You will also need to complete the Final Exam.  In order to “pass” this course, you will need to earn a 70% or higher on the FinalExam.  Your score on the exam will be tabulated as soon as you complete it.  If you do not pass the exam, you may take it again.

Time Commitment: This course should take you a total of 60 hours to complete. Each unit includes a “time advisory” that lists the amount of time you are expected to spend on each subunit.  These should help you plan your time accordingly.  Please look at the time advisories prior to starting the course to determine how much time you have over the next few weeks to complete eachunit.

Tips/Suggestions: This is a very difficult course, so allow time to “digest” the material. When needed, review relevant information from the prerequisite courses.  Take plenty of notes and review daily.

Course Overview

  • 2.1.6 Conformational Analysis  
  • 2.1.6.1 Newman Projections and Free Energy Diagrams  
  • 2.1.6.2 Hyperconjugation  
  • 2.2 Reaction Mechanisms  
  • 2.2.1 Kinetics  
  • 2.2.1.1 Rate Laws  
  • 2.2.1.2 Rate Determining Step  
  • 2.2.1.3 Steady-State Approximation  
  • 2.2.2 Hammond Postulate  
  • 2.2.3 Curtin-Hammett Principle  
  • 2.2.4 Factors That Influence the Rate of a Reaction  
  • 2.2.5 Reactions of Alkyl Halides  
  • 2.2.5.1 SN1 and SN2 Mechanisms  
  • 2.2.5.2 E1 and E2 Mechanisms  
  • Unit 3: Organometallics and Heterocycles  

    Remember that organometallics is the study of metals bonded to nonmetals, and there is an overlap of studying organometallics in both organic and inorganic chemistry.  In your previous organic chemistry courses, you have seen organometallic reagents in the form of Grignards, metal hydrides, and so forth.  Here, we will discuss organometallics more in depth, more specifically as carbon nucleophiles.  We will then examine the classes of organic heterocyclic compounds, which are compounds that contain at least two different elements as ring-member atoms. 

    Unit 3 Time Advisory
    This unit should take you approximately 9.5 hours to complete.

    ☐    Subunit 3.1: 4.5 hours


    ☐    Subunit 3.1.1: 4.5 hours

    ☐    Subunit 3.1.1.1: 2 hours

    ☐    Subunit 3.1.1.2: 2.5 hours

    ☐    Subunit 3.2: 5 hours


    ☐    Subunit 3.2.1: 0.5 hours

    ☐    Subunit 3.2.2: 0.5 hours

    ☐    Subunit 3.2.3: 0.5 hours

    ☐    Subunit 3.2.4: 0.5 hours

    ☐    Subunit 3.2.5: 0.5 hours

    ☐    Subunit 3.2.6: 0.5 hours

    ☐    Subunit 3.2.7: 0.5 hours

    ☐    Subunit 3.2.8: 0.5 hours

    ☐    Subunit 3.2.9: 0.5 hours

    ☐    Subunit 3.2.10: 0.5 hours

    Unit3 Learning Outcomes
    Upon successful completion of this unit, the student will be able to:

    • Define organometallic chemistry.

    • Identify organometallic compounds.

    • Explain the reactions of organometallic compounds.

    • Identity heterocyclic compounds.

    • Name heterocyclic compounds.
  • 3.1 Organometallics  
  • 3.1.1 Organometallics as Carbon Nucleophiles  
  • 3.1.1.1 Addition to Carbonyls  
  • 3.1.1.2 Conjugate Addition  
  • 3.2 Classes of Organic Heterocyclic Compounds  
  • 3.2.1 Pyridine  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyridines are presented.

  • 3.2.2 Quinoline  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of quinolines are presented.

  • 3.2.3 Isoquinoline  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of isoquinolines are presented.

  • 3.2.4 Pyrroles  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyrroles are presented.

  • 3.2.5 Azoles  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of azoles are presented.

  • 3.2.6 Furan  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of furans are presented.

  • 3.2.7 Thiophene  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of thiophenes are presented.

  • 3.2.8 Pyridazine  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyridazines are presented.

  • 3.2.9 Pyrimidine  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyrimidines are presented.

  • 3.2.10 Pyrazine  

    Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyrazines are presented.

  • Unit 4: Final Exam