CHEM222 Organic Chemistry II

Department of Science, Technology, Engineering & Mathematics: Chemistry

I. Course Number and Title
CHEM222 Organic Chemistry II
II. Number of Credits
5 credits
III. Number of Instructional Minutes
IV. Prerequisites
CHEM221 (C or better)
V. Other Pertinent Information

Three-hour lecture, one-hour lab discussion and three-hour laboratory per week. Safety glasses or goggles required.

This course meets the General Education requirement for Technological Competence.

VI. Catalog Course Description
This course is a continuation of Chemistry 221 with an emphasis on aromatic and carbonyl chemistry. Spectroscopy and chromatography are integrated into the lecture and laboratory. Compounds are analyzed using classical and instrumental methods.
VII. Required Course Content and Direction

Organic Chemistry II (CHEM 222), along with Organic Chemistry I (CHEM 221), provides the fundamental background in organic chemistry necessary for biology and chemistry majors. It also fulfills the requirements of pre-medical, pre-dental, pharmacy, chiropractic, and chemical engineering schools.

As one of the Natural Sciences, chemistry has evolved out of careful observation and experimentation; as technology evolves, so does the body of chemical knowledge. This course will integrate relevant technological advances and their impact in the formulation of chemical principles and their applications. The laboratory component of the course will help to illustrate and apply some of these technological advances.

The course integrates and complements the information studied in CHEM221, and prepares the student for the study of more advanced topics, including polymers, biochemistry, and molecular biology. Emphasis is on aromatic and carbonyl chemistry. Topics include structure, stereochemistry, nomenclature, synthesis, properties, and reactions of these compounds.

The laboratory course contains examples of some important synthetic reactions in organic chemistry, as well as a set of experiments aimed at the identification of organic compounds. Both chromatographic techniques and instrumentation are involved, whenever possible, in the execution of these experiments.

  1. Course Learning Goals

    Students will:

    1. analyze the structure of organic compounds by recognizing main functional groups, naming the compounds using the I.U.P.A.C. system, and predicting their properties using the type of bonding, hybridization state, intermolecular forces, stereochemistry, conjugation, resonance, and aromaticity;
    2. describe mechanisms of reactions: electrophilic aromatic substitution, nucleophilic addition, pericyclic reactions, in addition to those learned in Organic I, and apply this knowledge to predict the major product in organic reactions, such as those involving hydrocarbons, alcohols, alkyl halides, and alkenes;
    3. analyze the nature of a reagent as a nucleophile, free radical, or electrophile and use this knowledge to propose the synthesis of organic compounds, such as hydrocarbons, alkyl halides, alcohols, ethers, alkenes, alkynes, aromatics, amines, and carbonyl containing compounds;
    4. use the characteristics of the common functional groups to understand the formation and properties of larger molecules, i.e., synthetic polymers and biomolecules: carbohydrates, peptides, and lipids; and
    5. demonstrate proficiency in organic laboratory skills as they pertain to: chemical information, safe handling, use and disposal of organic compounds; synthetic procedures, including isolation, purification, and structure elucidation of obtained products; use of multi-step synthesis; stoichiometry and use of instrumentation; and writing of laboratory notebooks and reports in accordance with current scientific journal styles [Technological Competence].
  2. Planned Sequence of Topics and/or Learning Activities

    Course Outline:

    1. Alkynes: Structure, Nomenclature, Properties, Preparation, and Reactions
    2. Dienes: Structure, Nomenclature and Reactions, Polymers and Polymerization
    3. Arenes and Aromaticity: Structure, Nomenclature, and Reactions
    4. Spectroscopy: NMR, IR, MS, UV
    5. Organometallic Compounds: Structure, Nomenclature, Preparation, and Reactions
    6. Alcohols: Preparation and Reactions
    7. Ethers and Epoxides: Structure, Nomenclature, Preparation, and Reactions
    8. Aldehydes and Ketones: Structure, Properties, Preparation, Reactions, and Analysis
    9. Carboxylic Acids: Reactions, Synthesis, and Spectroscopy
    10. Acyl Transfer Reactions: Carboxylic Acids Derivatives
    11. Amines: Preparation, Physical Properties, and Reactions
    12. Aryl Halides: Bonding, Reactions, and Mechanisms
    13. Phenols: Structure, Preparations, Reactions, and Analysis
    14. Ester Enolates: Condensation Reactions

    Laboratory Experiments:
    While specific laboratory experiments vary depending on the instructor and the semester, the following list is representative of the experiments that are used:

    1. Check-in, Safety Regulations
    2. Organic Reactions (Computer Program)
    3. Polymers and Plastics: Polyesters and Polyamide (Nylon)
    4. Liquid-Liquid Extraction
    5. Grignard Reaction: Preparation of Benzoic Acid
    6. Preparation of Methyl Benzoate
    7. Nitration of Methyl Benzoate
    8. Friedel-Crafts Acylation
    9. Vacuum Distillation FC Product
    10. Cannizaro Reaction
    11. HPLC
    12. Reduction of FC Product
    13. Computer Unknowns Identification
    14. NMR

    Learning Activities:
    Instruction aims to enable the student to:

    1. recognize functional groups in organic compounds;
    2. name organic compounds using the I.U.P.A.C. system;
    3. analyze the structure of a given compound and predict the type of bonding, hybridization state, and effect of the structure on the physical properties of such a compound;
    4. apply the concepts of conjugation, resonance, and aromaticity on the prediction of the behavior of some compounds;
    5. write and understand mechanisms for the different types of organic reactions: electrophilic aromatic substitution, electrophilic addition, pericyclic reactions, in addition to the ones covered in Organic Chemistry I;
    6. predict the major product in an organic reaction, such as those involving alkynes, aromatic compounds, carbonyl containing compounds, and amines, by applying the knowledge of reaction mechanisms;
    7. write a scheme for the synthesis of different classes of organic compounds, such as alkynes, ethers, aromatic compounds, amines, and carbonyl containing compounds;
    8. standardize and operate laboratory instruments to identify reactants and products and to separate mixtures of compounds;
    9. execute multi-step synthesis in the laboratory; calculate the yield after isolation and purification, identify the products of the reactions by physical, chemical, and spectroscopic tests;
    10. identify a given organic unknown compound by using physical, chemical, and spectroscopic data;
    11. prepare laboratory reports in accordance with current scientific journal styles;
    12. utilize the characteristics of the common functional groups to understand the formation and properties of larger molecules, i.e., synthetic polymers and biomolecules, such as carbohydrates, peptides, and lipids;
    13. obtain information about chemical compounds from all possible reference sources, apply this information for the safe handling, use, and disposal of such compounds in an environmentally responsible manner;
    14. work as a member of a team in solving classroom problems and in the laboratory;
    15. use appropriate computer programs to enhance learning;
    16. use appropriate current technology and instrumentation (microwave, FT-IR, NMR, HPLC) in the laboratory to obtain and analyze data; and
    17. understand the impact that this latest technology has on the field.
  3. Assessment Methods for Course Learning Goals

    Course learning goals are continuously assessed by periodic written examinations, class exercises, laboratory preparation, laboratory results, laboratory reports, and assigned work.
  4. Reference, Resource, or Learning Materials to be used by Student:

    The students will use approved text, laboratory modules and handouts, laboratory and demonstration equipment, library, science learning center, computer programs, and internet links. Please refer to the course syllabus for specific information.

Review/Approval Date - 2/99; Revised 6/08; New Core 8/2015