Foothill CollegeApproved Course Outlines

Physical Sciences, Mathematics & Engineering Division
CHEM 12BORGANIC 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 continuation of CHEM 12A. Emphasis is on structure-reactivity relationships of organic compounds, mechanisms of functional group transformations, and synthesis of organic target compounds from simple precursors. Laboratory provides extensive practice in the synthesis, purification, isolation and characterization of organic target molecules. For chemistry, biological science, environmental science majors, and for pre-professional students in dentistry, medicine, pharmacy, veterinary medicine or any other interested students who have mastered the prerequisites.
Prerequisite: CHEM 12A.
Co-requisite: None
Advisory: None

2. Course Objectives -
The student will be able to:
  1. Predict the outcome of chemical reactions involving alkenes, alkynes, dienes and aromatic compounds.
  2. Apply theoretical models that address the structure-reactivity relationships of organic compounds.
  3. Gain further proficiency in proposing the detailed mechanism of a chemical transformation in Organic Chemistry.
  4. Design multi-step syntheses of organic target molecules from simple precursors.
  5. Interpret spectroscopic data to elucidate structural information about an organic compound.
  6. Acquire skill in the preparation, isolation, purification and identification of organic compounds using common laboratory techniques.
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 laboratory bench locker containing specialized glassware and equipment for both mini and micro-scale organic synthesis. Instrumentation maintained for shared routine use includes analytic balances, Melting Point apparatti, Polarimeters, Gas Chromatographs, UV-Visible spectrometers, FTIR spectrometers, GC-MS and 1H/Multinuclear 60 MHz FTNMR.

4. Course Content (Body of knowledge) -
  1. Predict the outcome of chemical reactions involving alkyl halides, alkenes, alkynes, dienes and aromatic compounds.
    1. Alkyl halides
      1. Properties
      2. Formation
        1. via nucleophilic displacement
        2. via Free Radical Halogenation of Alkanes
          1. Mechanism and Reaction Energy Profile
          2. Product distribution as a function of Statistics and relative Selectivity
          3. Selectivity and Hammonds Postulate
    2. Alkenes
      1. Properties
      2. Pi molecular orbitals and alkene reactivity
      3. Preparation of Alkenes
        1. From alkyl halides and alkyl sulfonates
        2. From alcohols
      4. Reactivity of Alkenes
        1. Hydrogenation
        2. Oxymercuration-demurcuration
        3. Addition of hydrogen halides
        4. Addition of halogens
        5. Formation of halohydrins
        6. Anti-Markovnikov syn addition in Hydroboration-oxidation
        7. Addition of Peroxycarboxylic acids
        8. Vicinal syn dihydroxylation with osmium tetroxide
        9. Oxidative cleavage by ozonolysis
        10. Anti-Markovnikov Radical addition of HBr
        11. Polymerization
    3. Alkynes
      1. Properties
      2. Preparation from Dihalides via double elimination
      3. Reactivity of Alkynes
        1. Acidity
        2. Reaction of Alkynyl anions with alkyl halides and epoxides
        3. Hydrogenation to alkanes with Pd, Pt, Ni or Rh; to cis alkenes with Lindlar catalyst; to trans alkenes with Sodium in liquid ammonia
        4. Formation of Markovnikov Ketone via reaction with water with acid or mercury (II) catalyst
        5. Formation of Aldehyde or Ketone via Hydroboration-Oxidation
        6. Reaction with molecular halogens to form di- or tetra-halides
        7. Reaction with HX to make geminal dihalides
    4. Delocalized pi systems
      1. Relative Stability
      2. Acidity
      3. Polar addition of HX, H3O+ or X2
      4. The Diels-Alder reaction
      5. Polymerization of conjugated dienes
    5. Benzene and Aromaticity
      1. Predicting aromaticity and anti-aromaticity
      2. Electrophilic Aromatic Substitution
        1. Nitration
        2. Sufonation
        3. Halogenation
        4. Friedel-Crafts alkylation and acylation
      3. Synthesis of poly-substituted aromatics
      4. Oxidation of benzylic carbon
  2. Apply theoretical models that address the structure-reactivity relationships of organic compounds.
    1. Kinetic vs Thermodynamic control in addition of electrophiles to conjugated dienes
    2. Pi molecular orbitals and Molecular Orbital Energy Diagrams of pi systems in conjugated acyclic and cyclic polyenes
    3. Stereo- and regio- selectivity in the Diels-Alder reaction: endo vs exo adducts.
    4. Predicting Aromaticity and Anti-Aromaticity from Molecular Orbital Energy Diagrams.
    5. Relative reactivity and Directing effects of aromatic substituents in Electrophilic Aromatic Subsitution
    6. Computational Chemistry of substituted benzene
    7. Apply Hammonds postulate to predict the relative selectivity of a reaction under Kinetic Control.
  3. Gain further proficiency in proposing the detailed mechanism of a chemical transformation in Organic Chemistry.
    1. Propose the mechanism of a reaction sequence from knowledge of individual reaction mechanisms.
  4. Design multi-step syntheses of organic target molecules from simple precursors.
    1. Recognize the limitations of known reactions with regard to the need for selectivity in polyfunctional organic compounds.
    2. Assess the advantages and disadvantages of alternative strategies in the synthesis of an organic target compound.
  5. Interpret spectroscopic data to elucidate structural information about an organic compound.
    1. Nuclear Magnetic Resonance
      1. Spin quantum number and interaction with magnetic field
      2. Chemical Shift
      3. Spin Coupling
      4. Peak Integration
      5. Sensitivity and Resolution: low field vs high field spectrometers
      6. Chemical Equivalence and magnetic equivalence
      7. First order versus Second order spectra
      8. Diastereotopicity
      9. Given the molecular formula and the 1H NMR spectrum, deduce the structure of simple organic compounds
    2. Infrared Spectroscopy
      1. Molecular Vibrations and absorption of IR em radiation
      2. Characteristic IR bands of common functional groups
      3. Strengths and limitations of IR spectroscopy
    3. Mass Spectrometry
      1. Electron ionization
      2. Features of mass spectra useful in structure elucidation:
      3. Fragmenting patterns and stability of radical cations
      4. The molecular ion peak and molar mass
      5. Isotopic abundance and M+1 or M+2 signals
    4. UV-Vis spectroscopy
      1. Electronic energy levels and absorption of UV-Vis em radiation
      2. Color and extended conjugation
    5. Synthesize data from MS, IR, 1H and 13C NMR to determine the structure of an unknown organic compound.
5. Repeatability - Moved to header area.
 
6. Methods of Evaluation -
  1. 1-3 Quizzes: answer and/or M/C
  2. 2-3 Lecture Examinations : short answer and M/C
  3. 2-3 Laboratory Examinations: short answer and M/C
  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. Acquire skill in the preparation, isolation, purification and identification of organic compounds using common laboratory techniques.
    1. Safely handle hazardous chemicals
      1. Waste Handling
      2. Hazardous Chemicals: MSDS
    2. Synthesis of Organic Compounds
Examples include:
  1. Multi-step syntheses of 4-Bromoaniline from Nitrobenzene
  2. Bromination of trans-cinnamic acid
  3. Selective reduction of 3-nitroacetophenone
  4. The Diels-Alder reaction between butadiene and maleic anhydride
  5. Acid-Catalyzed Dehydration of 3-methylcyclohexanol
  • Identification
    1. Measure Physical Properties (mp or bp, mixed mp)
    2. Identification of unknown Alcohols by NMR
    3. Acquire FTNMR (1H or 13C) and/or FTIR spectra on isolated products
  • Isolate/Purify
    1. Column Chromatography and TLC of an unknown mixture
    2. Distillation
    For example, in Steam distillation of Aniline following reduction of nitrobenzene with Sn/HCl and in distillation of methylcyclohexene products following dehydration of 3-methylcyclohexanol
  • Routine Extraction and Recrystallization
  • Gas Chromatographic separation of products from Acid-Catalyzed Dehydration of 3-methylcyclohexanol
  • Assess the optimal method for isolation or purification of an impure organic compound.
  • Learn to maintain complete and accurate records of experiments.
  • Develop competency in writing thorough laboratory reports.
  •  
    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 Written Laboratory Reports including Discussion of Interpretation of Results and Conclusions
    2. Short Answer Examination Questions
    3. Weekly reading assignments from both lecture and laboratory texts.
    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 14:43:06


    Foothill CollegeApproved Course Outlines