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. Four hours of lecture and three hours of lab weekly.

5. Placement Tests Required:

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

1. Program-Applicable Courses – This course fulfills a requirement for the following program(s):

Criminalistics, AS Degree

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:

• Draw Lewis structures from condensed structural formulas.  MnTC Goal 3
• Construct and name structural formulas for alkanes, cycloalkanes, alkenes, alkynes and haloalkanes.  MnTC Goal 3
• Use curved arrows and push electrons to create contributing resonance structures.  MnTC Goal 3
• Identify and assign R and S configurations to chiral centers.  MnTC Goal 3
• Draw potential energy diagrams and correlate staggered and eclipsed conformations of acyclic alkanes.  MnTC Goal 3
• Predict the relative strength of acids based on molecular structure.  MnTC Goal 3
• Predict the reaction products for electrophilic addition, hydroboration-oxidation, reduction and ozonolysis of alkenes.  MnTC Goal 3
• Predict the reaction products from the electrophilic addition, hydration and reduction of alkynes.  MnTC Goal 3
• Plan an organic synthesis using retrosynthetic analysis.  MnTC Goal 3
• Draw the mechanisms for electrophilic addition reactions of HX, H₂O and X₂ of alkenes.  MnTC Goal 3
• Draw the mechanism for halogenation of alkanes.  MnTC Goal 3
• Define the following terms; SN1, SN2, E1, E2, and draw generic mechanisms involving haloalkanes.  MnTC Goal 3
• Predict the reaction mechanism (SN1, SN2, E1, E2) and the products formed for the substitution and elimination reactions of haloalkanes based on the structure of the haloalkane, the properties of the nucleophile and properties of the solvent.  MnTC Goal 3
• Perform a melting point determination of an organic unknown.  MnTC Goal 3
• Use molecular modeling software to compose three-dimensional structural formulas.  MnTC 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. Lab Techniques
3. Recrystallization of Benzoic Acid
4. Recrystallization of Napthalene
5. Choosing a Recrystallization Solvent
6. Fractional Distillation
7. Separation of Three Solids
8. Extraction of Caffeine
9. Column Chromatography
10. Bromine to Cinnamic Acid
11. Phenylpropynoic Acid by Double Dehydrobromination of Cinnamic Acid
12. Sn2 Reactions