I. General Information

1. Course Title:
Organic Chemistry I

2. Course Prefix & Number:
CHEM 2472

3. Course Credits and Contact Hours:

Credits: 5

Lecture Hours: 4

Lab Hours: 3

Internship Hours: 0

4. Course Description:

This course involves a thorough coverage of the aliphatic and aromatic classes of compounds involving the study of structure, nomenclature, physical properties, preparation, reactions and analysis of these compounds. Also included is the study of reaction mechanisms. MnTC Goal 3

5. Placement Tests Required:

Accuplacer (specify test):

No placement tests required

Score:

6. Prerequisite Courses:

9. Co-requisite Courses:

There are no corequisites for this course.

II. Transfer and Articulation

1. Course Equivalency - similar course from other regional institutions:

St. Cloud State University, CHEM 310 Organic Chemistry I, 5 credits
Bemidji State University, CHEM 2311 Organic Chemistry I, 3 credits
Bemidji State University, CHEM 2371 Organic Chemistry Laboratory I, 1 credit

III. Course Purpose

2. MN Transfer Curriculum (General Education) Courses - This course fulfills the following goal area(s) of the MN Transfer Curriculum:
Goal 3 – Natural Sciences

IV. Learning Outcomes

1. College-Wide Outcomes

College-Wide Outcomes/Competencies	Students will be able to:
Demonstrate written communication skills	Complete written reports using data collected from the laboratory.
Apply abstract ideas to concrete situations	Predict physical properties of matter using atomic and molecular theories.
Work as a team member to achieve shared goals	Work together as team members to successfully complete laboratory experiments.

2. Course Specific Outcomes - Students will be able to achieve the following measurable goals upon completion of the course:

• Predict properties and reactivity of organic molecules using concepts of molecular structure, formal charge, and resonance (Goal 3);
• Translate between compound names and representations of structure (Goal 3);
• Analyze the relative energies of molecular structures (Goal 3);
• Create and employ 3-dimensional structures to determine the constitutional and stereochemical isomeric relationships between molecules (Goal 3);
• Identify various functional groups within complex molecules, correlate physical properties with functional group structure, and predict relevant reactions each functional group will undergo (Goal 3);
• Predict the products of acid-base, substitution, elimination, and addition reactions through the application of thermodynamic and kinetic principles (Goal 3);
• Create logical synthetic strategies by combining reactions into practical multi-step sequences (Goal 3);
• Propose reaction mechanisms using the curved-arrow formalism (Goal 3); and
• Employ data from NMR, IR, and UV-VIS spectroscopy and mass spectrometry to identify compounds and demonstrate an understanding of how each of these analytical techniques work (Goal 3);
• Plan organic chemical reactions using proper reaction stoichiometry calculations (Goal 3);
• Perform successful organic chemical reactions with hands-on use of reaction glassware and equipment, practicing proper laboratory technique to maximize product yield and purity (Goal 3);
• Separate and purify chemical compounds (Goal 3);
• Determine the identity of organic samples through physical and spectroscopic methods (Goal 3);
• Determine the qualitative and quantitative purity of organic samples through physical and spectroscopic methods (Goal 3);
• Model the scientific method by performing inquiry- or research-based laboratory experiments or projects in which the student makes decisions regarding experimental design and execution (Goal 3);
• Demonstrate responsible laboratory safety and waste handling practices including the use of proper fume hoods or fume extraction for chemicals that emit hazardous vapors (Goal 3); and
• Communicate the procedure, results, and relative success of an experiment with respect to the experimental objectives in the form of a laboratory notebook, written reports, or verbal presentation (Goal 3). 

V. Topical Outline

Listed below are major areas of content typically covered in this course.

1. Lecture Sessions

1. Covalent Bonding and Shapes of Molecules
• Electronic Structure of Atoms
• Lewis Model of Bonding
• Functional Groups
• Bond Angles and Shapes of Molecules
• Polar and Nonpolar Molecules
• Resonance
• Quantum or Wave Mechanics
• The Molecular Orbital and Valence Bond Theories of Covalent Bonding
2. Alkanes and Cycloalkanes
• The Structure of Alkanes
• Constitutional Isomerism in Alkanes
• Nomenclature of Alkanes
• Cycloalkanes
• The IUPAC System--A General System of Nomenclature
• Conformations of Alkanes and Cycloalkanes
• Cis, Trans Isomerism in Cycloalkanes
• Physical Properties of Alkanes and Cycloalkanes
• Reactions of Alkanes
3. Stereoisomerism and Chirality
• Stereoisomerism
• Chirality—The Handedness of Molecules
• Naming Chiral Centers—The R,S System
• Acyclic Molecules with Two or More Chiral Centers
• Cyclic Molecules with Two or More Chiral Centers
• Properties of Stereoisomers
• Optical Activity—How Chirality Is Detected in the Laboratory
• Separation of Enantiomers Resolution
4. Acids and Bases
• Arrhenius Acids and Bases
• Bronsted-Lowry Acids and Bases
• Acid Dissociation Constants, pK_a, and the Relative Strengths of Acids and Bases
• The Position of Equilibrium in Acid-Base Reactions
• Molecular Structure and Acidity
• Lewis Acids and Bases
5. Alkenes: Bonding, Nomenclature, and Properties
• Structure of Alkenes
• Nomenclature of Alkenes
• Physical Properties of Alkene
6. Reactions of Alkenes
• Reactions of Alkenes--An Overview
• Reaction Mechanisms
• Electrophilic Additions
• Hydroboration-Oxidation
• Oxidation
• Reducton
• Molecules Containing Chiral Centers as Reactants or Products
7. Alkynes
• Structure of Alkynes
• Nomenclature of Alkynes
• Physical Properties of Alkynes
• Acidity of 1-Alkynes
• Preparation of Alkynes
• Electrophilic Addition to Alkynes
• Hydration of Alkynes to Aldehydes and Ketones
• Reduction of Alkynes
• Organic Synthesis: Retrosynthetic Analysis
8. Haloalkanes, Halogenation, and Radical Treactions
• Structure
• Nomenclature
• Physical Properties of Haloalkanes
• Perparation of Haloalkanes by Halogenation of Alkanes
• Mechanism of Halogenation of Alkanes
• Allylic Halogenation
• Radical Autoxidation
• Radical Addition of HBr to Alkenes
9. Nucleophilic Substituton and b-Elimination
• Nucleophilic Substitution in Haloalkanes
• Solvents for Nucleophilic Substitution Reactions
• Mechanisms of Nucleophilic Aliphatic Substitution
• Experimental Evidence for S_N1 and S_N2 Mechanisms
• Analysis of Several Nucleophilic Substitution Reactions
• b-Elimination
• Mechanisms of b-Elimination
• Experimental Evidence for E1 and E2 Mechanisms
• Substitution Versus Elimination

2. Laboratory/Studio Sessions

1. Chemical Drawing, Online Resources
2. Determining Melting Point
3. Recrystallization of Benzoic Acid and Aspirin
4. Determination of Boiling Point
5. Identifying an Unknown Analgesic by Melting Temperature and Chromatography
6. Separation of Organic Compounds by Acid-Base Extraction
7. Understanding Polarimetry
8. Investigating Gas Chromatography
9. Fractional Distillation of Esters
10. Extraction of Spinach Pigments & Analysis by Electronic Absorption Spectroscopy
11. S_N1: Synthesis of tert-Butyl Chloride
12. S_N2: Synthesis of 1-Bromobutane