Foothill CollegeApproved Course Outlines

Physical Sciences, Mathematics & Engineering Division
CHEM 12AORGANIC CHEMISTRYSummer 2013
4 hours lecture, 2 hours lecture-laboratory, 4 hours laboratory.6 Units

Total Quarter Learning Hours: 120 (Total of All Lecture, Lecture/Lab, and Lab hours X 12)
 
 Lecture Hours: 4 Lab Hours: 4 Lecture/Lab: 2
 Note: If Lab hours are specified, see item 10. Lab Content below.

Repeatability -
Statement: Not Repeatable.

Status -
 Course Status: ActiveGrading: Letter Grade with P/NP option
 Degree Status: ApplicableCredit Status: Credit
 Degree or Certificate Requirement: AS Degree
 GE Status: Non-GE

Articulation Office Information -
 Transferability: BothValidation: 07/01/2009; 11/14/12

1. Description -
This course is the first of a three Sophomore level course describing the chemistry of organic (carbon containing) compounds. Emphasis on structure-reactivity relationships, mechanisms of functional group transformations, and the preparation, and purification of organic compounds. For biological science, chemistry,environmental science majors and students pursuing careers in dentistry, medicine, pharmacy, or veterinary medicine. Generally not appropriate for nursing majors (see CHEM 30B)
Prerequisite: CHEM 1C.
Co-requisite: None
Advisory: None

2. Course Objectives -
The student will be able to:
  1. Apply current theories of Bonding to an understanding of Molecular Structure and reactivity.
  2. Understand the importance of both Kinetics and Thermodynamics to the outcome of a chemical reaction
  3. Understand the concept of Chirality in organic compounds and its importance in Biological Systems
  4. Name, Draw and Interpret three-dimensional representations of Organic Molecules
  5. Recognize the relationship between structure and reactivity through a study of functional groups in organic molecules
  6. Practice common laboratory techniques to acquire skill in the preparation, isolation and purification of Organic compounds
3. Special Facilities and/or Equipment -
A chemistry laboratory is provided with adequate chemicals and equipment for conducting the prescribed course. Each student is issued a desk locker containing specialized glassware for both mini and micro-scale organic synthesis. Five feet of Fume Hood space is allocated to each pair of students. Instrumentation maintained for routine use includes analytical balances, Melting Point apparatti, Polarimeters, Gas Chromatographs, UV-Visible spectrometer, FTIR spectrometer, GC-MS and broad-band 60 MHz FTNMR spectrometer.

4. Course Content (Body of knowledge) -
  1. Apply current theories of Bonding to an understanding of Molecular Structure and reactivity
    1. Atomic Orbitals and Hybridization: Shapes and relative energies of atomic orbitals
    2. Molecular Orbitals: sigma and pi bonding and antibonding orbitals
    3. Molecular Orbital Energy Diagrams: Identifying HOMO and LUMO
    4. Drawing Lewis Structures including Resonance and Formal Charge
    5. Recognizing resonance stabilized molecules and ranking the relative contributions of resonance forms
  2. Understand the importance of both Kinetics and Thermodynamics to the outcome of a chemical reaction
    1. The concept of Mechanism in Organic Chemistry: curved arrow formalism and Reaction Energy Diagrams.
    2. Predicting Rate laws from a known mechanism and utilizing rate information to confirm or refute a proposed mechanism.
    3. Hammonds Postulate applied to SN1 reactions
    4. Solvent effects on reaction rate
    5. Recognizing Kinetic versus Thermodynamic Control in a reaction
  3. Understand the concept of Chirality in organic compounds and its importance in Chemical Systems
    1. Identification of Stereocenters, Chiral and MESO compounds.
    2. Distinguishing between Stereoisomers, Conformers and Constitutional Isomers
    3. Assessing the stereochemical relationship between organic molecules: Enantiomers and Diastereomers
    4. Optical Activity of Chiral Molecules, enantiomeric excess and optical purity.
    5. Interpreting stereochemical designations (R,S versus +,)
    6. Predicting the stereochemical outcome of a chemical reaction from an interpretation of its mechanism: Inversion vs retention in SN1, SN2, E1 and E2 reactions
  4. Name, Draw and Interpret three-dimensional representations of Organic Molecules
    1. Nomenclature of Alkanes, Alkyl Halides, Alcohols and Ethers
      1. IUPAC rules
      2. Common Names
      3. Assigning Absolute Configuration to Stereocenters: R, S Nomenclature
    2. Conformations of Organic Compounds: Rotation about carbon-carbon single bonds
      1. Conformational Energy Diagrams
      2. Drawing and Interpreting Newman Projections: Eclipsed versus Staggered; Gauche versus Anti Conformations
      3. Torsional Strain versus Steric Strain
      4. The Chair Conformation of Cyclohexane
      1. Axial versus Equatorial substituted Cyclohexane
      2. Cis/Trans isomerism in Disubstituted Cyclohexane
      3. Predicting the position of conformational equilibrium in substituted cyclohexane
      4. Skeletal/ Bond-line structural representations of organic compounds
      5. Wedge-Dash formalism
    3. Recognize the relationship between structure and reactivity through a study of functional groups in organic molecules
      1. Identify Bronsted Acids and Bases and predict the position of their equilibria in solution.
        1. Predicting Acid strength as a function of anionic conjugate base stability
        2. Assessing relative stablility of conjugate base as a function of structural features
          1. electronegativity of atom bearing charge
          2. size of atom bearing charge
          3. resonance delocalization of charge
          4. hybridization state of atom bearing charge
          5. Inductive effect on neighboring charge
      2. Recognize Electrophiles and Nucleophiles and understand their central role in Organic Reactions
      3. Identifying Functional Groups in Organic Compounds
      4. Structure and relative stability of Alkanes
        1. Physical properties of Alkanes
        2. Heats of Combustion as a measure of relative Stability
      5. Predict the physical properties and chemical reactivity of Alkyl Halides, Alcohols, Ethers and Epoxides
        1. Alkyl Halides
          1. Structure and Properties of Alkyl Halides
          2. Reactivity of Alkyl Halides with Nucleophiles in SN2, SN1, E2 and E1 reactions
          3. Predicting the dominant product in a competing reaction environment through assessment of relevant variables
            1. The Substitution pattern of the Alkyl Halide (1, 2 or 3 RX)
            2. The Nucleophilic strength of the Nucleophile (kinetic measure)
            3. The Base strength of the Nucleophile (thermodynamic measure)
            4. The Solvent
            5. Protic versus aprotic
          4. Polarity and the Dielectric Constant
        2. Alcohols and Thiols
        1. Structure and Physical Properties of Alcohols and Thiols
        2. Reactivity of Alcohols as weak acids or bases
          1. Alcohols as electrophiles in reaction with hydrogen halides, PX3, SOCl2, POCl3 and sulfonyl chlorides
          2. Conversion to Alkyl Sulfonates for reaction with anionic nucleophiles
          3. Rearrangement of Carbocations from Alcohols in strong acid
          4. Hyperconjugation and Carbocation Stability
          5. Oxidation of Alcohols with Cr(VI): chromic acid versus PCC
          6. Thiols as Bronsted Acids and as Nucleophiles
      6. Ethers and Epoxides
        1. Structure and Physical Properties of Ethers and Epoxides
        2. Reactivity of ethers as electrophiles in reaction with hydrogen halides or other strong acids in water.
        3. Reactivity of epoxides as electrophiles in reaction with nucleophiles
          1. Under acidic conditions with regioselectivity at more substituted carbon (HX, H3O+)
          2. Under basic conditions with regioselectivity at less substituted carbon (Nuc:-, LiAlH4)
      7. Formation of Alcohols, Ethers and Thiols from nucleophilic substitution reactions
5. Repeatability - Moved to header area.
 
6. Methods of Evaluation -
  1. Multiple Quizzes: short answer and/or M/C
  2. 2-3 Lecture Examinations : predominantly short answer
  3. 2-3 Laboratory Examinations: predominantly short answer
  4. Written laboratory reports
  5. Final cumulative examination : short answer and M/C
7. Representative Text(s) -
Smith, Janice. Organic Chemistry, 3rd ed. McGraw-Hill Science/Engineering/Math, New York, 2010.
Wade, L.G. Organic Chemistry, 7th ed. Prentice Hall, 2010.
Solomons, T.W. Graham, Organic Chemistry, 9th ed. John Wiley & Sons, 2009.
Klein, D., Organic Chemistry, 1st ed. John Wiley & Sons, 2011.
Mohrig, Hammond, Schatz and Morrill, Modern Projects and Experiments in Organic Chemistry: Miniscale and Williamson Microscale, 2nd. Ed. W.H. Freeman and Co., 2003.
Mohrig, Hammond, Schatz and Morrill, Techniques in Organic Chemistry W.H. Freeman and Co., 2003.

8. Disciplines -
Chemistry
 
9. Method of Instruction -
  1. Lecture
  2. Discussion
  3. Group work
 
10. Lab Content -
  1. Practice common laboratory techniques to acquire skill in the preparation, isolation and purification of Organic compounds
    1. Simple and Fractional Distillation of Ethanol produced from fermentation of sucrose
    2. Steam Distillation of Limonene extracted from Orange Peel
    3. Polarimetry of Limonene extract
    4. Thin Layer Chromatography to characterize and assess the purity of an unknown
    5. Column Chromatography to separate a mixture of Ferrocene and Acetyl-Ferrocene
    6. Acid-Base Extraction of an mixture of a carboxylic acid and neutral organic of unknown structure.
    7. Identification of Organic Compounds by Mixed Melting Point
    8. Recrystallization from single and mixed solvents
    9. Microscale Distillation in the acid catalyzed Rearrangement of an alcohol
    10. Microscale Extraction and Recrystallization
    11. Acquisition and Interpretation of Infrared Spectra for Functional Group Identification
    12. Laboratory Notebook Preparation
    13. Precision/Error Assessment
    14. Data Analysis
    15. Hazardous material and Waste Handling
 
11. Honors Description - No longer used. Integrated into main description section.
 
12. Types and/or Examples of Required Reading, Writing and Outside of Class Assignments -
  1. Weekly Laboratory Reports using standard Scientific Notebook Entries including Discussion and interpretation of Results and Conclusion
  2. Short-Essay Examination questions
  3. Weekly reading assignments from both Lecture and Laboratory Textbooks
13. Need/Justification -
This course is a required core course for the A.S. degree in Chemistry.


Course status: Active
Last updated: 2014-03-11 14:42:01


Foothill CollegeApproved Course Outlines