Foothill CollegeApproved Course Outlines

Physical Sciences, Mathematics & Engineering Division
CHEM 12CORGANIC 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: 11/26/12

1. Description -
A continuation of CHEM 12B describing the reactivity of organic (carbon containing) compounds including biologically active molecules such as proteins and carbohydrates. Continued emphasis on structure-reactivity relationships, mechanisms of functional group transformations, multi-step syntheses and laboratory methods of synthesis, purification, isolation and characterization of target organic molecules. For biological science, chemistry, and environmental science majors as well as any pre-professional students studying for careers in dentistry, medicine, pharmacy, veterinary medicine and any other interested students who have mastered the prerequisites.
Prerequisite: CHEM 12B.
Co-requisite: None
Advisory: None

2. Course Objectives -
The student will be able to:
  1. Predict the properties and reactivity of an expanding group of mono-functional organic molecules including Aldehydes, Ketones, Carboxylic Acids, Carboxylic Acid Derivatives, Nitriles, beta-dicarbonyls, and Amines
  2. Recognize classes of polyfunctional natural products including Carbohydrates and Amino Acids and predict the fundamental properties and chemical reactivity of each
  3. Propose the syntheses of an expanded array of target organic molecules from simple precursors using strategies which incorporate both regio- and stereo-selectivity of reactions, and selectivity in polyfunctional compounds
  4. Analyze data to discern the validity of a hypothesis
  5. Interpret NMR, IR, UV-Vis and MS spectroscopic data for the elucidation of molecular structure
  6. Acquire skill in the routine operation of FT-NMR and FT-IR instrumentation
  7. Acquire skill in the preparation, purification and identification of organic compounds using common laboratory techniques including reflux, distillation, extraction, recrystallization, chromatography (GC,TLC and LC), and melting/boiling point determinations
  8. learn to maintain complete and accurate records of experiments and develop competency in writing thorough descriptions of chemical phenomena
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 apparatus, polarimeters, gas chromatographs, UV-Visible spectrometers, FTIR spectrometers, and 1H/Multinuclear 60 MHz FT-NMR, and Gas Chromatograph-Mass Spectrometer (GC-MS)

4. Course Content (Body of knowledge) -
  1. Predict the properties and reactivity of an expanding group of mono-functional organic molecules including Aldehydes, Ketones, Carboxylic Acids, Carboxylic Acid Derivatives, Nitriles, β-dicarbonyls, and Amines
    1. Ketones and Aldehydes
      1. Physical Properties
      2. Formation
        1. oxidation of alcohols
        2. hydration of alkynes via hydroboration oxidation or oxymercuration
        3. ozonolysis of an alkene
      3. Reactivity of Ketones and Aldehydes
        1. Reversible reaction with water or alcohols
        2. Reaction with amines to form imines or enamines
        3. Reaction with cyanide or acetylide anions
        4. Reaction with phosphorus ylides: The Wittig Reaction
        5. Reaction with Grignard reagents and Organolithium reagents
        6. Reduction with Sodium borohydride or lithium aluminum hydride
        7. Acidity and formation of Enolates
        8. Reaction at α-carbon
          1. Reaction with LDA under Kinetic vs Thermodynamic Control
          2. α-alkylation
          3. α-halogenation under basic and acidic conditions
          4. The Haloform Reaction
          5. The Aldol reaction
          6. β-diketones: formation via Michael addition
          7. Robinson annulation
    2. Carboxylic Acids
      1. Physical Properties
      2. Relative Acidity of substituted carboxylic acids
      3. Preparation
        1. Via oxidation of alcohols or aldehydes
        2. Via oxidation of benzylic carbon
        3. Via hydrolysis of nitriles
        4. Via Grignard reaction with alkyl, vinyl or aryl halides and CO2
      4. Reactivity
        1. with thionyl chloride and phosphorous tribromide to form acid halides
        2. with carboxylic acid chlorides to form anhydrides
        3. with alcohols and catalytic mineral acids to form esters
        4. with amines to form amides
        5. with LiAlH4 to form alcohols
        6. with molecular bromine and PBr3 to form alpha-brominated acids
    3. Comparison of Carboxylic Acid derivatives
      1. Relative reactivity of acid chlorides, anhydrides, esers, carboxylic acids, and amides: correlation to leaving group ability
      2. Interconversion of derivatives via addition-elimination mechanism
    4. Reactivity of Acid Chlorides
      1. Reduction of acid chlorides with lithium tri(tert-butoxy)aluminum hydride to form aldehydes
      2. Reaction of acid chlorides with organocuprates to form ketones
      3. Interconversion to anhydrides, esters, carboxylic acids and amides via addition-elimination mechanism
    5. Reactivity of Esters
      1. Reduction with LiAlH4 and DIBALH
      2. Reaction with Grignard reagents
      3. Reaction at α-carbon
        1. Claisen Condensation
        2. Decarboxylation of β-ketoacids
        3. Variation: Ketone nucleophile + ester electrophile
        4. Intramolecular: Dieckmann Reaction
        5. Biochemical versions of Claisen: Acetyl coA conversion to isopentylpyrophosphate (terpene
      4. b-ketoesters
        1. alkylation
        2. Malonic ester synthesis
        3. Acetoacetic ester synthesis of methyl ketones
    6. Reactivity of Amides
      1. Hofmann rearrangement of amides with halogens in aqueous base
      2. Reduction with LiAlH4 and DIBALH
      3. Hydrolysis with acid or base catalyst
    7. Reactivity of Nitriles
      1. Hydrolysis to amides and carboxylic acids
      2. Reaction with Grignard reagents to form ketones
      3. Reaction with LiAlH4 and DIBALH to form amines and aldehydes, respectively
    8. Conversion of electrophilic acyl derivatives to nucleophilic acyl anions
      1. via 1,3-Dithiaalkanes
      2. via catalysis with thiazolium salts
    9. Amines
      1. Properties
      2. Preparation
        1. From other amines via nucleophilic substitution
        2. From nitriles, amides and azides via reduction
        3. Gabriel synthesis
        4. From aldehydes and ketones via reductive amination
      3. Reactivity
        1. Hofmann Elimination
        2. Mannich reaction
        3. Nitrosation of amines and diazoinium ions
    10. Substituted Benzene
      1. Reactivity of Benzylic carbon
        1. Oxidation
        2. Substitution
        3. Acidity
      2. Nucleophilic Aromatic Substitution
        1. Addition-elimination mechanism
        2. Benzyne intermediate
      3. Reactions of aryl diazonium ions
        1. With water
        2. The Sandmeyer reaction: Reaction with Cu(I) salts
        3. Reduction with H3PO2
      4. Reactivity of Phenols
        1. Electrophilic substitution
        2. Claisen rearrangement
        3. Oxidation to quinones
        4. Oxidation-reduction processes in nature
  2. Recognize classes of polyfunctional natural products including Carbohydrates and Amino Acids and predict the fundamental properties and chemical reactivity of each Carbohydrates
    1. Carbohydrates
      1. Monosaccharides
        1. Fischer projections and D,L-nomenclature
        2. Cyclic forms and mutarotation
        3. Optical activity and structure determination
        4. Reactivity
          1. reducing sugars: reaction with Fehlings and Tollens solutions
          2. Oxidative cleavage with periodic acid
          3. Condensation with amine derivatives
          4. esterification and alkylation of hydroxy-groups
          5. formation of glycosides
          6. glycosides and mutarotation
          7. sugar chain extension by cyanohydrin formation and reduction
          8. sugar chain shortening by Ruff degradation
      2. Disaccharides: formation and hydrolysis
    2. Amino acids and peptides
      1. Structure
      2. Acid/Base properties
      3. Synthesis of Amino Acids
        1. SN2 reaction of ammonia with α-haloacid
        2. Diethyl acetamidomalonate alkylation, hydrolysis and decarboxylation
      4. Peptides : Primary structure
        1. The peptide bond
        2. Sequencing
        3. Cleavage
          1. With aqueous acid at every peptide bond
          2. With cyanogen bromide BrCN at methionine C terminus
          3. With chymotripsin at phe, tyr, trp
          4. With Tripsin at lys, arg
          5. Using Edman Degradation
          6. DNFB to identify N-terminus
          7. Separation and Identification of aa fragments via Gel electrophoresis, Ion-exchange chromatography, and Mass Spectrometry
        4. Peptide Synthesis
          1. Traditional solution synthesis
          2. Merrifield Solid Phase synthesis
  3. Propose the syntheses of an expanded array of target organic molecules from simple precursors using strategies which incorporate both regio- and stereo-selectivity of reactions, and selectivity in polyfunctional compounds
    1. Polysubstituted Aromatics
    2. Amino Acids and di-peptides
    3. Selective Reactions of b-dicarbonyl derivatives
    4. Comprehensive functional group transformations: Interconversion of all functional group categories discussed throughout the 12ABC sequence
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. Laboratory
  3. Discussion
  4. Group work
 
10. Lab Content -
  1. Analyze data to discern the validity of a hypothesis
    1. Determine the Equilibrium constant between a carboxylic acid and its acetate ester via both 1H NMR and Gas Chromatography
    2. Determine the stereoselectivity of borohydride reduction under conditions of Kinetic Control
  2. Interpret NMR, IR, UV-Vis and MS spectroscopic data for the elucidation of molecular structure
    1. Determine the structure of an unknown low molecular weight organic compound from its spectra alone
    2. Evaluate original spectra to confirm the identity of a product
  3. Acquire skill in the routine operation of FT-NMR and FT-IR instrumentation
    1. Acquisition of 1H NMR and IR spectra following isolation of organic products
    2. Acquisition of 13C NMR of organic unknowns
    3. Utilizing 1H NMR spectra to determine equilibrium constants between acetate esters and their associated alcohols
  4. Acquire skill in the preparation, purification and identification of organic compounds using common laboratory techniques including reflux, distillation, extraction, recrystallization, chromatography (GC,TLC and LC), and melting/boiling point determination
    1. α,β-unsaturated ketones via Aldol-Dehydration using Unknown aldehydes and Ketones
    2. Carboxylic acid via the Haloform reaction
    3. Ester synthesis via Fischer Esterification of unknown alcohols
    4. Amine synthesis via selective reduction of 4-nitroacetophenone
    5. Multi-step synthesis: formation of hydrobenzoin dimethyl acetal from benzaldehyde
    6. Qualitative analysis of unknowns by chemical diagnostic testing
    7. Independent strategic planning of experimental procedures
  5. learn to maintain complete and accurate records of experiments and develop competency in writing thorough descriptions of chemical phenomena
    1. Preparation of laboratory reports for each experiment
    2. Completion of Formal laboratory report using ACS guidelines
    3. Explaining structure-reactivity relationships or other empirical data in short-answer responses to examination questions
 
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. Reading Assignments: Weekly reading assignments from the textbook discussing the principles that govern organic reactions (e.g., electron flow, structure/reactivity relationship, etc.)
  2. Laboratory Experiments: Each experiment must be read thoroughly and pertinent information is placed in a laboratory notebook. Information includes chemical reaction mechanisms, theoretical yield calculations, physical properties of reagents, safety hazard information, and experimental procedure(s).
  3. Laboratory Reports: A logical, concise discussion of data that is analyzed to draw a conclusion about the purpose of the experiment.
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 14:43:55


Foothill CollegeApproved Course Outlines