Organic Chemistry I

I.     Course Prefix/Number: CHM 223

       Course Name: Organic Chemistry I

       Credits: 4 (3 lecture; 3 lab)

II.    Prerequisite

CHM 122 with a minimum grade of C or consent of instructor.

III.   Course (Catalog) Description

Course is first of two-course sequence (CHM 223 and CHM 224). Content presents theories, structures, and reactions of organic chemistry, including the properties of various functional groups; bonding and structure of organic molecules; properties and reactions of aromatic and aliphatic hydrocarbons and alkyl halides; stereochemistry; spectroscopy, including infrared and nuclear magnetic resonance; reaction intermediates and mechanisms such as nucleophilic substitutions and electrophilic additions; and multi-step organic synthesis. Weekly, hands-on lab activities, including preparations, separations, and identifications of organic compounds. Identical to CHM 221 except that CHM 223 includes two three-hour labs per week, rather than one three-hour lab per week.

IV.   Learning Objectives

  1. Lecture
    1. Apply the three models of bonding–Lewis, valence bond and molecular orbital theory–as well as their extensions–hybridization and resonance–to describe covalent bonding in organic species.
    2. Draw and interconvert drawings of neutral and charged organic species using condensed formulae, bond-line formulae, Newman projections, sawhorse projections and Fisher projections.
    3. Name organic molecules and functional groups using systematic nomenclature defined by the International Union of Pure and Applied Chemistry (IUPAC).
    4. Rank organic species according to physical and chemical properties, including polarity, boiling point, heat of combustion, acidity, solubility, bond strength, stability and reactivity, based on their structural features.
    5. Classify isomers as either constitutional or one of the categories of stereoisomer: conformational, configurational, geometrical, optical, enantiomer, diastereomer and meso.
    6. Relate analytical data, including optical rotation, infrared (IR) spectroscopy, mass spectrometry, nuclear magnetic resonance (NMR) spectroscopy and ultraviolet (UV) spectroscopy to structural features in organic molecules.
    7. Illustrate the thermodynamic and kinetic properties of chemical reactions by constructing a reaction coordinate diagram that illustrates the relative energies of reactants, products, intermediates and transition states as well as labels quantities of enthalpy and activation energy.
    8. Draw mechanisms and their transition states for radical reactions and polar reactions as well as the interconversion of resonance structures using curved-arrow notation.
    9. Predict the products of and conditions required for: addition reactions to alkenes and alkynes; substitution reactions of alcohols and alkyl halides, alkylation reactions of alkynes; elimination reactions of alcohols and alkyl halides; the Diels-Alder reaction; electrophilic aromatic substitution; and nucleophilic aromatic substitution.
    10. Identify and describe the physical and chemical properties of conjugated systems and aromatic compounds.
    11. Design synthetic routes to organic molecules using retrosynthetic analysis.
  2. Laboratory
    1. Minimize risk to self and others by adhering to documented and verbalized laboratory safety policies.
    2. Operate instrumentation, such as an infrared spectrometer, melting point device, and polarimeter, independently to acquire data relevant to an experiment.
    3. Assemble glassware apparatuses to perform techniques such as distillation, extraction and chromatography.
    4. Document laboratory procedures, observations, analyses and conclusions in a laboratory notebook according to scientific standards.

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. Structure and Bonding
      1. Atoms, Electrons and Orbitals
      2. Covalent and Ionic Bonding
        1. Models of Bonding in H2: Lewis, valence bond and molecular orbital theory
        2. Polar covalent bonds and electronegativity
        3. Electrostatic potential maps
        4. Valence electrons, formal charge and the octet rule
      3. Structural formulas of organic molecules
        1. Introduction to classes of hydrocarbons (alkanes, alkenes, alkynes and arenes)
        2. Condensed formula and bond-line formula drawings
        3. Constitutional isomers and stereoisomers
        4. Resonance structures
      4. Shapes of simple organic molecules
        1. Valence-Shell Electron Repulsion Theory (VSEPR)
        2. Molecular dipole moments
      5. Hybridization model of bonding
        1. sp3, sp2, and sp hybridization of carbon
        2. bonding in ethane, ethylene and acetylene
        3. bonding in water and ammonia: hybridization of oxygen and nitrogen
        4. relationship of carbon s-character to electronegativity and bond-strength
    2. Acid-Base Properties of Organic Species
      1. Arrhenius, Bronsted-Lowry and Lewis definitions
      2. Acid-base equilibria and conjugates; Calculting Keq from pKas
      3. Reaction coordinate diagrams and relationships between ∆H, Ka and pKa
      4. Mechanism of protonation and deprotonation using curved-arrow notation
      5. Structural effects on acid strength
        1. Enthalpy of reactants and products
        2. Resonance stabilization of anionic conjugate bases
    3. Alkanes
      1. IUPAC nomenclature of branched alkanes
      2. Trends in physical and chemical properties of alkanes
        1. boiling point, equilibrium vapor pressure, heat of combustion
        2. Van der Waals forces: London-dispersion forces
      3. Conformational stereoisomers of ethane, butane and higher alkanes
    4. Cycloalkanes
      1. Shapes and bond angles of cylcoalkanes
      2. Angle strain and heat of combustion
      3. Conformations of cyclohexane
        1. Axial and equatorial bonds
        2. Chair inversion (ring-flipping)
      4. Conformational analysis of mono and disubstituted cyclohexanes
    5. Stereochemistry
      1. Molecular chirality
        1. Carbon chirality center
        2. Planes and points of symmetry as tests for achiral molecules
      2. Enantiomers and their physical properties
      3. Cahn-Ingold-Prelog R-S notation
      4. Optical activity
      5. Diastereomers, meso forms and their physical properties
      6. Chirality centers other than carbon
        1. Sulfur (sulfoxides) and nitrogen (amines)
        2. Pyramidal inversion of nitrogen
      7. Fisher projections
    6. Analytical Techniques for Characterizing Organic Molecules
      1. Mass Spectrometry
      2. Infrared Spectroscopy
      3. Nuclear Magnetic Resonance
      4. Ultraviolet-visible spectroscopy
    7. Kinetic and Thermodynamic Properties of Chemical Reactions
      1. Reaction coordinate diagrams (intermediates, enthalpy of reaction, activation energy)
      2. Transition-state theory and reaction rates
      3. Hammond postulate
      4. Drawing transition-states
    8. Alcohols and Alkyl Halides
      1. IUPAC nomenclature and classes of alkyl halides and alcohols
      2. Trends in physical properties (boiling point, solubility, polarity)
        1. Intermolecular forces: dipole-dipole
        2. Intermolecular forces: London-dispersion forces
      3. Preparation of alkyl halides from alcohols by substitution reactions
        1. Reactivity of alcohols and hydrogen halides toward substitution
        2. Mechanisms of SN1 and SN2 processes
        3. Structure, bonding and stability of carbocations
        4. Nucleophiles and Electrophiles
        5. Stereochemistry of SN1 reactions
        6. Nucleophilic substitution of alkyl sulfonates
        7. Solvent effects on the rate of substitution
      4. Preparation of alkyl halides by radical halogenation of alkanes
        1. Structure, bonding and stability of carbon free radicals
        2. Regioselectivity of chlorination and bromination; Hammond’s postulate
    9. Alkenes and their Elimination Reactions
      1. IUPAC nomenclature and geometrical isomers (cis/trans and E/Z notation)
      2. Physical properties and relative stability by degree of substitution
      3. Preparation of alkenes by dehydration of alcohols, dehydrohalogentaion of alkyl halides and elimination of alkyl sulfonates
        1. Mechanisms of E1 and E2 reactions
        2. Stereoselectivity
        3. Regioselectivity: Zaitsev and Hofmann rules
        4. Anti eliminations in E2 reactions: stereoelectronic effects
        5. Rearrangements in alcohol dehydration
        6. Competition between substitution and elimination reactions
    10. Alkenes: Addition Reactions
      1. Hydrogenation: Stereoselective syn addition of H2
      2. Electrophilic addition of hydrogen halides and sulfuric acid
        1. Regioselectivity: Markovnikov’s rule
        2. Mechanistic basis for Markovnikov’s rule
      3. Hydroboration-oxidation
        1. Syn-addition (concerted) mechanism for hydroboration
        2. Regioselectivity
      4. Halogen addition and halonium ions
      5. Formation of vicinal halohydrins through anti-addition
      6. Free-radical addition of hydrogen bromide
      7. Epoxidation
      8. Ozonolysis
    11. Alkynes
      1. IUPAC nomenclature
      2. Acidity of terminal alkynes
      3. Alkylation of acetylenes
      4. Preparation through double dehydrohalogenation
      5. Addition reactions of alkynes
        1. Hydrogenation
        2. Stereoselective hydrogenation to cis-alkenes (Lindlar catalyst)
        3. Metal-ammonia reduction to trans-alkenes
        4. Halogenation
        5. Hydration to ketones and hydroboration-oxidation to aldehydes
    12. Conjugation in Alkadienes and Allylic Systems
      1. Classes, stability, bonding and resonance energy of dienes
      2. Substitution reactions of allylic and benzylic halides
      3. Preparation by elimination reactions
      4. Addition of hydrogen halides and halogens: kinetic and thermodynamic pathways
      5. Diels-Alder reaction: mechanism and regioselectivity
    13. Arenes and Aromaticity
      1. Structure and stability of benzene
        1. Frontier molecular orbitals of benzene and its closed-shell configuration
        2. Resonance energy: heat of hydrogenation of benzene vs. (Z)-1,3,5-hexatriene
        3. IUPAC nomenclature of substituted derivatives of benzene
      2. Aromatic and Antiaromatic Species, Including Ions
        1. Huckel’s rule and closed-shell configurations
        2. Molecular orbital diagrams from Frost circles
        3. Heterocyclic aromatic compounds
      3. Electrophilic aromatic substitution (SE-Ar)
        1. Arenium ions and the mechanism of SE-Ar
        2. Nitration, sulfonation, halogenation
        3. Friedel-Crafts alkylation and acylation
        4. Synthesis of alkylbenzenes by acylation-reduction (Clemmensen/Wolf-Kishner)
        5. Substituent effects on regioselectivity (orth-para directors, meta-directors)
        6. Substituent effects on rate (activating and deactivating groups)
      4. Nucleophilic aromatic substitution
        1. Nitro-substituted arenes
        2. Addition-elimination mechanism
  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. Orientation to the Laboratory and Calibration of Equipment
    2. Physical Properties of Organic Compounds
    3. Solubility
    4. Purification of a Solid by Recrystallization
    5. Extraction
    6. Constitution Isomers and Nomenclature
    7. Molecular Modeling and Conformers
    8. Chirality and Stereoisomers
    9. Fractional Distillation
    10. Infrared Spectroscopy
    11. Steam Distillation
    12. Preparation of an Alkene
    13. Dichlorocarbene Addition to an Alkene
    14. Introduction to Synthesis
    15. Chromatography
    16. Preparation of tert-pentyl chloride
    17. Reactivities of Alkyl Halides: SN1 and SN2 Reactions
    18. Dehydrohalogenation: An E2 Reaction
    19. Nuclear Magnetic Resonance Spectroscopy
    20. TLC Separation and Analysis of Analgesics
    21. Isolation of the Active Ingredient in a Commercial Analgesic
    22. A Diels-Alder Reaction
    23. Nitration of Methyl Benzoate
    24. Preparation of Acetylsalicylic Acid (Aspirin)

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: Introduction to Organic Laboratory 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.