CHEM221 Organic Chemistry I

Department of Science, Technology, Engineering & Mathematics: Chemistry

I. Course Number and Title
CHEM221 Organic Chemistry I
II. Number of Credits
5 credits
III. Number of Instructional Minutes
IV. Prerequisites
CHEM122 (C or better), or CHEM220 (C or better), or a grade of B+ or better in both CHEM101 and CHEM102
V. Other Pertinent Information
Three-hour lecture, one-hour lab discussion and three-hour laboratory per week. Safety glasses or goggles required.
VI. Catalog Course Description
The preparation, properties, and reactions of the more important classes of carbon compounds are studied in this lecture and laboratory course. Emphasis is on reaction mechanisms, stereochemistry, and functional group characteristics. The laboratory stresses synthetic methods and techniques. Compounds are analyzed using classical and instrumental methods.
VII. Required Course Content and Direction

Chemistry 221, Organic Chemistry I, is an advanced level chemistry course for science majors. It is designed, when followed by CHEM 222, Organic Chemistry II, to fulfill the organic chemistry requisites for biology and chemistry majors, as well as for pre-medical, pre-dental, pharmacy, chiropractic, and chemical engineering schools. Students registering for CHEM 221 must have a good background in general chemistry. Knowledge of chemical bonding, structure and physical properties, acid-base theory, kinetics, and equilibrium are fundamental for the concept-building approach of organic chemistry.

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. Furthermore, the laboratory component of the course will help to illustrate and apply some of these technological advances.

Organic chemistry provides the student with the necessary background to understand the chemistry of carbon-containing compounds. Topics will include structure, stereochemistry, nomenclature, synthesis, properties, and reactions of the major classes of organic compounds. A non-mathematical, mechanistic approach is used in the course to explain the reactions of these compounds.

The laboratory component consists of a series of experiments that illustrate synthesis of organic compounds, fermentation chemistry and natural products isolation. A strong emphasis is put on analytical techniques for product separation and purification, as well as on instrumentation as a tool for studying properties and characterization of the isolated compounds.

  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 and stereochemistry;
    2. describe mechanisms of reactions: free radical, nucleophilic substitution, elimination and electrophilic addition, 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 a hydrocarbons, alkyl halides, alcohols, or alkenes; and
    4. 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; stoichiometry and use of instrumentation; and writing of laboratory notebooks and reports in accordance with current scientific journals styles.
  2. Planned Sequence of Topics and/or Learning Activities

    Course Outline:

    1. Introduction to Organic Chemistry
    2. Chemical Bonding: A Review
    3. Alkanes: Structure, Nomenclature, Properties, Sources, and Conformation
    4. Cycloalkanes: Structure, Nomenclature, and Conformational Analysis
    5. Alcohols and Alkyl Halides: Structures, Nomenclature, Properties, Preparation, and Mechanisms of Reactions
    6. Alkenes: Structure, Nomenclature, Properties, Preparation, and Mechanisms of Reactions
    7. Stereochemistry: Definitions, Analysis, and Reactions of Stereogenic Compounds
    8. Nucleophilic Substitution Reactions
    9. Alkynes: Structure, Nomenclature, Properties, Preparation, and Reactions
    10. Dienes: Structure, Nomenclature, and Reactions. Polymers and Polymerization
    11. Arenes and Aromaticity: Structure, Nomenclature, and 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. Literature Search
    3. Ethanol from Sucrose
    4. Preparation of Acetylsalicylic Acid
    5. Melting Point: An Index of Purity
    6. TLC Analysis of Analgesic Drugs
    7. GC Analysis of Hydrocarbons
    8. IR Determinations
    9. Boiling Point Determinations
    10. Paper Chromatography of Food Colors
    11. Refractometry
    12. Nucleophilic Substitution Reactions, Competing Nucleophiles
    13. Preparation of Cyclohexene
    14. Polarimetry

    Learning Activities:
    Instruction aims to enable the student to:

    1. recognize main 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. recognize nucleophiles, electrophiles and their reactivity, in order to predict the course of a reaction;
    5. write and understand mechanisms for the different types of organic reactions: free radical, nucleophilic substitution, elimination, and electrophilic addition;
    6. predict the major product in an organic reaction, such as those involving hydrocarbons, alcohols, alkyl halides, and alkenes, by applying the knowledge of reaction mechanisms;
    7. write a scheme for the synthesis of different classes of organic compounds, such as hydrocarbons, alcohols, alkyl halides, and alkenes;
    8. construct models of all the important classes of compounds, and predict their optical and structural isomers;
    9. standardize and operate laboratory instruments to identify reactants and products and to separate mixtures of compounds;
    10. synthesize a compound--for example, cyclohexene--in the laboratory, isolate and purify it, identify it by physical or chemical tests, and calculate its yield;
    11. prepare laboratory reports in accordance with current scientific journal styles;
    12. obtain information about chemical compounds from all possible reference sources; apply this information for the safe handling, use and disposal of such compounds in a safe and environmentally responsible manner;
    13. work as a member of a team in solving classroom problems and in the laboratory;
    14. use appropriate current technology in the laboratory to obtain data; and
    15. understand the impact that recent 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:

    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