Organic Chemistry II

I.     Course Prefix/Number: CHM 224

       Course Name: Organic Chemistry II

       Credits: 5 (3 lecture; 6 lab)

II.    Prerequisite

CHM 221 or CHM 223 with minimum grade of C, or consent of instructor.

III.   Course (Catalog) Description

Course is second of two-course sequence (CHM 223 and CHM 224). Content includes study of structure, nomenclature, properties and reactions of alcohols and phenols, aldehydes and ketones, carboxylic acids and their derivatives, amines, condensation reactions, polymers, and biomolecules. Weekly hands-on lab activities including preparations, separations, and identifications of organic compounds. Identical to CHM 222 except that CHM 224 includes two three-hour labs per week, rather than one three-hour lab per week.

IV.   Learning Objectives

  1. Lecture
    1. Relate the structure of organic molecules to their physical and chemical properties.
    2. Apply the Lewis model, valence bond model and molecular orbital theory of bonding as well as their extensions–hybridization and resonance–to describe covalent bonding in organic species.
    3. Draw and interconvert drawings of neutral and charged organic species as well as biomolecules using condensed formulae, bond-line formulae, Newman projections, sawhorse projections, Hawthorn projections and Fisher projections.
    4. Name organic molecules and functional groups using systematic nomenclature defined by the International Union of Pure and Applied Chemistry (IUPAC).
    5. Classify isomers as either constitutional or a category of stereoisomer.
    6. Rank organic species according to physical and chemical properties.
    7. Predict the products of and conditions required for chemical reactions of organic functional groups.
    8. Draw mechanisms (curved arrow notation) and transition states for radical reactions, polar reactions and the interconversion of resonance structures.
    9. Rationalize the regioselectivity, stereoselectivity, chemoselectivity and reactivity of chemical reactions.
    10. Construct reaction coordinate diagrams in order to illustrate the thermodynamic and kinetic properties of chemical reactions.
    11. Design synthetic routes to organic molecules and biomolecules using retrosynthetic analyses and appropriate protecting group strategies.
    12. Characterize biomolecules including carbohydrates, amino acids, peptides, proteins, nucleic acids and lipids.
    13. Propose reasonable biological pathways and mechanisms for anabolic and catabolic processes.
  2. Laboratory
    1. Minimize risk to self and others by adhering to documented and verbalized laboratory safety policies.
    2. Operate laboratory instruments independently to acquire data relevant to an experiment.
    3. Assemble and use apparatuses required for reaction, separation and purification techniques in organic chemistry.
    4. Document laboratory procedures, observations, analyses and conclusions in a laboratory notebook according to scientific standards.
    5. Build models of organic molecules and relate structural observations to physical and chemical properties.

V.    Academic Integrity and Student Conduct

Students and employees at Oakton Community College are required to demonstrate academic integrity and follow Oakton's Code of Academic Conduct. This code prohibits:

• cheating,
• plagiarism (turning in work not written by you, or lacking proper citation),
• falsification and fabrication (lying or distorting the truth),
• helping others to cheat,
• unauthorized changes on official documents,
• pretending to be someone else or having someone else pretend to be you,
• making or accepting bribes, special favors, or threats, and
• any other behavior that violates academic integrity.

There are serious consequences to violations of the academic integrity policy. Oakton's policies and procedures provide students a fair hearing if a complaint is made against you. If you are found to have violated the policy, the minimum penalty is failure on the assignment and, a disciplinary record will be established and kept on file in the office of the Vice President for Student Affairs for a period of 3 years.

Please review the Code of Academic Conduct and the Code of Student Conduct, both located online at
www.oakton.edu/studentlife/student-handbook.pdf

VI.   Sequence of Topics

  1. Lecture
    1. Alcohols and Phenols
      1. Nomenclature and physical properties of alcohols
      2. Redox reactions of alcohols, ketones and aldehydes
        1. Swern and Dess-Martin; modern methods
        2. Chromium oxidations
        3. Periodic acid cleavage of diols
        4. Hydride reductions of aldehydes and ketones
      3. Silyl and benzyl protecting groups for alcohols
      4. Grignard addition to ketones and aldehydes
        1. Basicity of Grignards
        2. Protecting group strategies
      5. Extraction of phenols, carboxylic acids and amines in aqueous solutions
      6. Electrophilic aromatic substitution of phenols (O vs. C-acylation and alkylation)
    2. Ethers and Thioethers
      1. Nomenclature and physical properties of ethers
      2. Crown ethers and ethers as solvents (e.g., role in Grigard reagents)
      3. Conformational analysis of pyran rings
      4. Crown ethers; role in nucleophilic substitution
      5. Preparation of Ethers
        1. Williamson ether synthesis
        2. Alcohol condensation
        3. Epoxidation by peroxyacids
        4. Biological oxidation of arenes; NIH shift
        5. Claisen rearrangement
        6. Alkylation of thiols; S-adenosylmethionine
      6. Reactions of ethers
        1. Acidic cleavage
        2. Ring opening of epoxides (acidic and alkaline)
    3. Nucleophilic Addition Reactions to Aldehydes and Ketones
      1. Nomenclature and physical properties of aldehydes and ketones
        1. Carbonyl bond strength
        2. Carbonyl polarity and its influence on boiling point and solubility
      2. Reactions of Ketones and Aldehydes
        1. Hydration equilibrium; rationalize Keq of various substrates
        2. Hyperconjugation and inductive effect on ground state carbonyl stability
        3. Cyanohydrin formation equilibrium
        4. Benzoin condensation; Umpolung
        5. Condensation with amines: imines and enamines
          1. pH dependence
          2. stabilized vs. nonstabilized imines
          3. Schiff bases from pyridoxal phosphate
          4. Reductive amination
          5. Wolf-Kishner reduction
        6. Acetal and hemiacetal formation
          1. As protecting groups
          2. Role of azeotropic distillation; Dean-Stark trap
        7. Wittig olefination
    4. Carboxylic Acids
      1. Nomenclature and physical properties
      2. Acidity of carboxylic acids
        1. Substituent effects on pKa
        2. Substituent effects through benzene (Hammett plot)
      3. Synthesis of Carboxylic acids
        1. Oxidation of alcohols and aldehydes
        2. Nitrile synthesis
      4. Reactions of Carboxylic acids
        1. Fisher esterification
        2. Lactonization
        3. Decarboxylation of diacids and ketoacids
        4. Biological decarboxylations
    5. Carboxylic acid derivatives
      1. Nomenclature and physical properties
      2. Addition/elimination mechanism; tetrahedral intermediate
      3. Relative reactivity of derivatives
      4. Interconveresion of derivatives
      5. Thionyl chloride in synthesis
      6. DCC and mixed anhydride methods for preparing amides
      7. Amine chemoselectivity vs. alcohol
      8. Saponification and transesterification; soap and biodiesel
      9. Grignard addition to esters and nitriles
      10. Biological reactions of thioesters; rationalizing nature’s choice
    6. Enols and Enolates
      1. Mechanism of enolation
      2. Relative acidity of carbonyl compounds
      3. Kinetic vs. thermodynamic enolates
      4. Reactions of enols and enolates
        1. Aldol, Claisen, Dieckman, acylation, alkylation
        2. Malonic ester synthesis
        3. Conjugate additions: cuprates vs. Grignards
        4. Michael addition, Robinson annulation
        5. Hell-Volhard-Zelinski monohalogenation of enols
        6. Haloform reaction of enolates
      5. Enolization and enol content (equilibrium)
    7. Amines
      1. Classification, nomenclature and physical properites
      2. Basicity of alkyl amines, aryl amines and amidines (imidazole and DBU)
      3. Amines at physiological pH (Henderson-Hasselbalch)
      4. Solubility and extraction of amines
      5. Synthesis of amines
        1. Lithium aluminum hydride reduction of amides and azides
        2. Amine alkylation; quaternary salts
        3. Gabriel amine synthesis
        4. Curtius rearrangement
        5. Hoffmann elimination rule/transition states
        6. Role as electron donating group in electrophilic aromatic substitution
        7. Formation of diazonium ions; Sandmeyer reactions
    8. Carbohydrates
      1. Classification and nomenclature
      2. Fisher projections; D and L monosaccharides
      3. Anomers of pyranoses and furanoses
      4. Mutarotation, optical rotation and the anomeric effect
      5. Redox reactions of carbohydrates
      6. Chain extension through cyanohydrins
      7. Chain shortening through Wohl degradation
      8. Glycoside synthesis by Koenigs-Knorr
      9. 1,4 and 1,6-disaccharides
    9. Amino Acids
      1. Classification
      2. Using Henderson-Hasselbalch to determine the major form at specific pH
      3. Calculate isoelectric point (pI)
      4. Synthesis of amino acids
        1. Hell-Volhard-Zelinski
        2. Reductive amination
        3. Acetamidomalonate synthesis
    10. Peptides and Proteins
      1. Classification
      2. Sequencing
        1. Sanger’s reagent
        2. Ninhydrin staining
        3. Edman degradation
        4. Enzyme hydrolysis
      3. Synthesis
        1. Amino acid protecting groups strategies
        2. DCC coupling
    11. Lipids
      1. Definition and classification
      2. Prostaglandins, steroids, triglycerides, waxes, phospholipids, fats and terpenes
    12. Chemistry of metabolic pathyways
      1. NIH shift
      2. ATP
        1. Structural basis for phosphorylation potential
        2. Phosphorylation mechanism
        3. Role in coupled reactions; shift Keq b 10^8
      3. Fatty-acid biosynthesis
      4. Prostaglandin biosynthesis
      5. Monoterpene biosynthesis
      6. Glycolysis
      7. Citric acid cycle
    13. Polymers
  2. Laboratory Activities. Includes lectures and demonstration of the location and use of laboratory safety equipment as well as the laboratory and safety policies of the college. There are weekly hands-on activities, which may include 24-30 of those listed below.
    1. Ethanol from Sucrose
    2. Preparation of Triphenylmethanol
    3. Dehydration of an Alcohol
    4. Alcohol Identification
    5. Coenzyme Synthesis of Benzoin
    6. Benzil
    7. Benzilic Acid
    8. Hydrolysis of Benzonitrile
    9. Properties of Aldehydes and Ketones
    10. Synthesis Drill
    11. Benzocaine
    12. Nomenclature of Acid Derivatives Drill
    13. Tetraphenylcyclopentadienone
    14. Tetraphenylnaphthalene
    15. Benzocaine
    16. Aldol Condensation
    17. Michael Reaction
    18. Enamine
    19. Sulfanilamide
    20. Properties of Amines
    21. Diazonium Salts
    22. Properties of Carbohydrates I and II
    23. Isolation of Casein from Milk
    24. Amino Acids
    25. Sequencing Amino Acids in Peptides
    26. Soaps
    27. Detergents
    28. Preparation of Polymers
    29. Photochemistry
    30. Luminol and Chemiluminescence

VII.  Methods of Instruction

Instructional methods vary by instructor and may include, but are not limited to:

  • Lectures, which may be supplemented with classroom discussion, building molecular models, viewing multimedia and the use of computer-based materials.
  • Individual and group problem solving
  • Assigned textbook readings
  • Handouts and assignments
  • Hands-on laboratory activities
  • Information literacy assignments

Course may be taught as face-to-face, hybrid or online course.

VIII. Course Practices Required

  • Attendance at lecture and laboratory sessions.
  • Writing Skills: Students are expected to write at the college level on homework, exams and written assignments.
  • Communication Skills: Students are expected to communicate the language and ideas of organic chemistry orally as well through written assignments. All students will be asked to answer questions during class and to participate in discussions and oral presentations.
  • Computer Skills: Students will need basic computer skills to complete written assignments using a word processor, to access online resources, including the D2L course management system, and to communicate with the instructor through email.
  • Completion of reading, problem solving, and report assignments by their respective due dates. Students are expected to complete assigned textbook and lab manual readings before each class meeting.
  • Adherence to standard safety practices while in the laboratory.
  • Maintaining a laboratory notebook.
  • Courses may be taught as face-to-face, hybrid or online course.

IX.   Instructional Materials

Note: Current textbook information for each course and section is available on Oakton's Schedule of Classes.

Required

  1. Lecture text: McMurray, John; Organic Chemistry, 8th edition, 2011, Brooks/Cole. ISBN-13: 978-0-8400-5444-9.
  2. Laboratory text: Organic Chemistry 222/224 Laboratory Manual June 2011 edition, Oakton Community College Department of Chemistry.
  3. Chemical Safety/Splash Goggles. These goggles must meet the following criteria:
    • Fit snuggly against the forehead and face, protecting against splashes
    • Be impact resistant; ANSI rating of Z87 or higher
    • Include only indirect venting

    Two varieties of such goggles compliant with the above criteria are available for purchase in the bookstore. Students may also elect to find an alternative source for purchase, as long as the goggles meet the above criteria and are approved by the instructor.

Recommended

  1. Techniques DVD: Churchill, Connie; Microscale Techniques in the Organic Laboratory, 2011, Oakton Community College. Also available online at http://video.oakton.edu.
  2. McMurray, John; Study Guide with Student Solutions Manual for McMurray’s Organic Chemistry, 8th Ed., 2011, Brooks/Cole.

X.    Methods of Evaluating Student Progress

Depending upon the instructor, any combination of the following assessments may be used to evaluate student progress and determine the course grade.

  • Attendance
  • Homework assignments
  • Quizzes, tests, and examinations, which may include essay, short answer, multiple choice, true/false, and problem solving questions
  • Individual and/or group written reports
  • Individual and/or group oral presentations
  • Individual and group problem solving
  • Information literacy assignments utilizing library and online resources
  • Laboratory assignments, reports, notebooks and practical exams

XI.   Other Course Information

Support services include open computer laboratories, the college library, and free tutoring through the Learning Center as well as office hours with the course instructor.



If you have a documented learning, psychological, or physical disability you may be entitled to reasonable academic accommodations or services. To request accommodations or services, contact the Access and Disability Resource Center at the Des Plaines or Skokie campus. All students are expected to fulfill essential course requirements. The College will not waive any essential skill or requirement of a course or degree program.

Oakton Community College is committed to maintaining a campus environment emphasizing the dignity and worth of all members of the community, and complies with all federal and state Title IX requirements.

Resources and support for
  • pregnancy-related and parenting accommodations; and
  • victims of sexual misconduct
can be found at www.oakton.edu/title9/.

Resources and support for LGBTQ+ students can be found at www.oakton.edu/lgbtq.