KERN COMMUNITY COLLEGE DISTRICT – CERRO COSO COLLEGE

CHEM C221 COURSE OUTLINE OF RECORD

  1. DISCIPLINE AND COURSE NUMBER:
    CHEM C221
  2. COURSE TITLE:
    Organic Chemistry I
  3. SHORT BANWEB TITLE:
    Organic Chem I
  4. COURSE AUTHOR:
    Stenger Smith, John D.
  5. COURSE SEATS:
    -
  6. COURSE TERMS:
    70 = Fall
  7. CROSS-LISTED COURSES:
  8. PROPOSAL TYPE:
    CC Course Revision
  9. START TERM:
    70 = Fall, 2013
  10. C-ID:
  11. CATALOG COURSE DESCRIPTION:
    This course covers structure and bonding, polar bonds, alkanes, cycloalkanes, stereochemistry, synthesis, structure and reactivity of alkenes, synthesis, structure and reactivity of alkynes, handedness in chemistry, synthesis, structure and reactivity of alkyl halides, carbocations, the concept of resonance, nucleophilic substitutions and eliminations, basic biochemistry, mass spectrometry, infrared, nuclear magnetic resonance and ultraviolet spectroscopy and aromaticity. This Organic Chemistry I course is taught according to standards developed by the American Chemical Society.

  12. GRADING METHOD

    Default:
    S = Standard Letter Grade
    Optional:
    P = Pass/No Pass;A = Audit
  13. TOTAL UNITS:
    5

  14. INSTRUCTIONAL METHODS / UNITS & HOURS:

    Method
    Min Units
    Min Hours
    Lecture
    4
    72
    Lab
    1
    54
    Activity
    0
    0
    Open Entry/Open Exit
    0
    0
    Volunteer Work Experience
    0
    0
    Paid Work Experience
    0
    0
    Non Standard
    0
    0
    Non-Standard Hours Justification:

  15. REPEATABILITY

    Type:
    Non-Repeatable Credit
  16. MATERIALS FEE:
    No
  17. CREDIT BY EXAM:
    No
  18. CORE MISSION APPLICABILITY:
    UC Transfer;Associate Degree Applicable (AA/AS);CSU Transfer
  19. STAND-ALONE:
    No

  20. PROGRAM APPLICABILITY

    Required:
    Elective:
    General Sciences (AA Degree Program)
    General Sciences AA (AA Degree Program)
    Liberal Arts: Mathematics & Science (AA Degree Program)

  21. GENERAL EDUCATION APPLICABILITY

    Local:
    IGETC:
    IGETC Area 5: Physical and Biological Sciences = 5A: Physical Science with Lab;
    CSU:
    CSU GE Area B: Physical and its Life Forms(mark all that apply) = B1 - Physical Science;
    CSU GE Area B: Physical and its Life Forms(mark all that apply) = B3 - Laboratory Sciences;
    UC Transfer Course:
    CSU Transfer Course:

  22. STUDENT LEARNING OUTCOMES Upon completion of the course, the student will be able to

    1. Evaluate and apply the concepts of structure and reactivity to alkanes, alkenes, alkynes, alkyl halides, aromatic rings, cis-trans isomerism, enantiomers, and constitutional isomers. Demonstrate the ability to recognize and analyze chemical structures, and to propose viable synthetic routes to make various organic chemical compounds.
    2. Apply the concepts of nucleophilic substitution, electrophilic substitution, carbocation mechanisms, carbanion mechanism, resonance, elimination, stereochemistry of reactions of all the functional groups covered in this course in order to provide accurate reaction mechanisms.
    3. Provide the correct structures of organic chemicals from the respective Mass Spectrometry results, Infrared Spectrum, Ultraviolet Spectrum and Nuclear Magnetic Resonance Spectrum, as well as provide the key attributes of the respective spectra from the chemical structures.
    4. Safely perform supervised hands-on laboratory experiments that involve analysis, purification and synthesis of organic compounds and to critically analyze and report the results of these experiments.
    5. Demonstrate advanced proficiency in the Scientific Method, including the modern experimental and empirical methodologies characteristic of Science
    6. Effectively communicate and analyze scientific results in writing, verbally and graphically.

  23. REQUISITES

    Prerequisite:

    CHEM C111

  24. DETAILED TOPICAL OUTLINE:

    Lecture:


     A. Structure and Bonding 
      1. Atomic Structure
      2. Covalent and Ionic Bonds
      3. Hybridization
      
     B. Bonding and Properties 
      1. Electronegativity
      2. Polar Bonds and Dipole Moment
      3. Resonance
      4. Acids and Basis

       

     

     C. Alkanes and Cycloalkanes 
      1. Functional Groups
      2. Alkane Isomers
      3. Naming Alkanes and Cycloalkanes
      4. Properties of Alkanes and Cycloalkanes
      5. Cis-Trans Isomerism

     

     D. Stereochemistry of Alkanes 
      1. Conformational Analysis
      2. Newman Projections
      3. Torsional, Steric and Ring Strain
      
     E. Organic Reactions Overview  
      1. Kinds of Reactions
      2. Radical Reactions
      3. Polar Reactions
      4. Equilibria, Rates and Energy
      5. Energy Diagrams, Transition States, and Intermediates
      6. Biochemical Reactions

     

     F. Alkenes  

      1. Uses  of Alkenes
      2. Naming Alkenes
      3. Structure and Isomerism in Alkenes
      4. Electorphilic Addition to Alkenes
      5. Carbocation Structure and Stability
      6. Carbocation Rearrangements

     

     G. Reaction of Alkenes    
      1. Preparation of Alkenes
      2. Addition of Halogens
      3. Halohydrin Formation
      4. Addition of Water
      5. Addition of Carbenes
      6. Hydrogenation
      7. Addition of Radicals (Polymerization) 


     H. Alkynes     

      1. Electronic Structures of Alkynes
      2. Naming Alkynes
      3. Preparation of Alkynes
      4. Addition of HX and X2
      5. Hyrdration
      6. Reduction
      7. Oxidative Cleavage
      8. Acidity of Alkynes
      9. Alkylation of Acetylide Anions


     I. Stereochemistry    

      1. Enantiomers
      2. Optical Activity
      3. Rules for Stereochemistry
      4. Diastereomers
      5. Fischer Projections
      6. Stereochemistry of Reactions
      7. Stereochemistry in Biological Systems

     

     J. Alkyl Halides    

      1. Naming Alkyl Halides
      2. Structure and Preparation of Alkyl Halides
      3. Allyl Radicals:  Another Look at Resonance
      4. Alkyl Halides from Alcohols
      5. Grignard Synthesis
      6. Organometallic Coupling Reactions
      7. Oxidation and Reduction

     

     K. Reactions of Halides  

      1. Nucleophilic Substitution and Elimination Overview
      2. SN2 Reaction
      3. SN1 Reaction
      4. E2 Reaction
      5. E1 Reaction
      6. Biological Substitution Reactions

     

     L. Infrared Spectroscopy and  Mass Spectrometry 


      1. Mass Spectrometry
      2. Interpreting Mass Spectra
      3. Infrared Spectroscopy
      4. Interpreting Infrared Spectra

     

     M. Nuclear Magnetic Resonance (NMR) 
      1. 13C NMR Chemical Shifts
      2. 13C NMR Methods and Uses
      3. 1H NMR  Chemical Shifts and Proton Equivalence
      4. 1H NMR Methods and Uses

     

     N. Conjugated Dienes and Ultraviolet Spectroscopy   
      1. Preparation and Structure of Conjugated Dienes
      2. Allylic Carbocations
      3. Thermodynamic Versus Kinetic Control 
      4. Diels-Alder Reaction
      5. Natural and Synthetic Rubbers/Products
      6. Ultraviolet Spectroscopy
      7. Interpreting Ultraviolet Spectroscopy
      8. The Spectroscopy of Colored Compounds

     

             O. Benzene and Aromaticity 

      1. Aromaticity and the 4n+2 Rule
      2. Stabilitization Energy
      3. Polycyclic Aromatic Compounds
      4. Molecular Orbital Structure of Benzene
      5. Aromatic Substitutions
      6. Alkylation and Acylations
      7. Substituent and Additivity Effects
      8. Nucleophilic Aromatic Substitution
      9. Benzyne
      10. Oxidation and Reduction of Aromatic Compounds
      11. Trisubstituted Benzenes
          

     

     

     

     

     

     

     

     

     

     

     

    Lab:

    Hands-On Laboratory Experiments

    1.  Preparation of Reagents

    2.  Isolation and Purification

    3.  Analysis and Yield

    4.  Report Submission

    The experiments performed in the laboratory portion of this course take place under the supervision of the instructor in a chemistry laboratory.  All experiments are hands-on and are designed to reinforce concepts learned in the classroom as well as to teach standard organic synthesis, purification and analysis methods.Examples include experiments on simple and fractional distillation, crystallization, synthesis and alkenes and electrophilic aromatic substitution.
     

  25. METHODS OF INSTRUCTION--Course instructional methods may include but are not limited to

    1. Demonstration;
    2. Discussion;
    3. Field trip;
    4. Group Work;
    5. Guest Lecturers;
    6. Instruction through examination or quizzing;
    7. Laboratory;
    8. Lecture;
    9. Outside reading;
    10. Problem Solving;
    11. Written work;

  26. OUT OF CLASS ASSIGNMENTS: Out of class assignments may include but are not limited to

    Homework Assignments: Problem Solving of selected textbook problems. Example: Students predict the products of an electrophilic aromatic substition reaction. Lab Reports: Written reports describing outcomes of experiments performed in the laboratory. Example: Students, after using both techniques, analyze the utility of simple versus fractional distillation. Research Papers: Analysis of scientific journal articles and media articles related to Science. Example: Students analyze the ongoing controversy about Arsenic-containing Bacteria When conditions permit, a field trip to the China Lake NAWC Chemistry Division is undertaken in place of a laboratory experiment. Example: Students are given a tour of the facility and are required to identify an ‘unknown’ organic chemical from analysis techniques such as Infrared Spectroscopy or Nuclear Magnetic Resonance.

  27. METHODS OF EVALUATION: Assessment of student performance may include but is not limited to

    Graded Exams: 2 Midterm exams and a comprehensive final exam. For example the final exam involves a problem in which the students must deduce a chemical structure from Nuclear Magnetic Resonance, Spectroscopy, and elemental analysis.

    Graded Lab Reports: These reports evaluate the student's ability to collect and analyze data, provide a conclusion, report percent yield and account for any errors and/or explain success or failure.

    Graded Homework Assignments: These assignments cover material in the text book and evaluate the student's ability to solve problems related to the current chapter.

    Participation: Students are evaluated for their participation in the classroom and especially in the laboratory.

  28. TEXTS, READINGS, AND MATERIALS: Instructional materials may include but are not limited to

    Textbooks
    McMurry, J. (2012) Organic Chemistry, 8th, Brookes/Cole
    Manuals
    Fieser, J., and Williamson, H.. (2011-01-01 00:00:00.0) Organic Experiments, Houghton Mifflin
    Periodicals
    Software
    Other
  29. METHOD OF DELIVERY:
    Face to face;
  30. MINIMUM QUALIFICATIONS:
    Chemistry (Masters Required);

  31. APPROVALS:

    Origination Date
    03/09/2012
    Last Outline Revision
    02/25/2011
    Curriculum Committee Approval
    04/20/2012
    Board of Trustees
    06/14/2012
    State Approval
    UC Approval
    30 = Spring 2007
    UC Approval Status
    Approved
    CSU Approval
    50 = Summer 2000
    CSU Approval Status
    Approved
    IGETC Approval
    30 = Spring 2007
    IGETC Approval Status
    Approved
    CSU GE Approval
    30 = Spring 2007
    CSU GE Approval Status
    Approved