I. General Information

1. Course Title:
Organic Chemistry II

2. Course Prefix & Number:
CHEM 2473

3. Course Credits and Contact Hours:

Credits: 5

Lecture Hours: 4

Lab Hours: 3

4. Course Description:

This course is a continuation of CHEM 2472 and 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. 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 311 Organic Chemistry 2, 4 credits
Bemidji State University, CHEM 2312 Organic Chemisry II, 3 credits
Bemidji State University, CHEM 2372 Organic Chemistry Laboratory II, 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 a team member 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 (MnTC Goal 3);
• Translate between compound names and representations of structure (MnTC Goal 3);
• Create and employ 3-dimensional structures to determine the constitutional and stereochemical isomeric relationships between molecules (MnTC 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 (MnTC Goal 3);
• Predict the products of oxidation, reduction, aromatic substitution, nucleophilic acyl addition, nucleophilic acyl substitution, and alpha carbon (enol and enolate) reactions through the application of thermodynamic and kinetic principles (MnTC Goal 3);
• Create logical synthetic strategies by combining reactions into practical multi-step sequences (MnTC Goal 3);
• Propose reaction mechanisms using the curved-arrow formalism (MnTC Goal 3);
• 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 (MnTC Goal 3);
• Identify structures and functions of macromolecules (MnTC Goal 3);
• Plan organic chemical reactions using proper reaction stoichiometry calculations (MnTC 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 (MnTC Goal 3);
• Separate and purify chemical compounds (MnTC Goal 3);
• Determine the identity of organic samples through physical and spectroscopic methods (MnTC Goal 3);
• Determine the qualitative and quantitative purity of organic samples through physical and spectroscopic methods (MnTC 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 (MnTC 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 (MnTC 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 (MnTC Goal 3.

V. Topical Outline

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

1. Lecture Sessions

1. Alcohols
• Structure and Nomenclature of Alcohols 
• Physical Properties of Alcohols
• Acidity and Basicity of Alcohols
• Reaction of Alcohols with Active Metals
• Conversion of Alcohols to Haloalkanes and Sulfonates
• Acid-Catalyzed Dehydration of Alcohols
• The Pinacol Rearrangement
• Oxidation of Alcohols
2. Ethers, Sulfides, and Epoxides
• Structure of Ethers
• Nomenclature of Ethers
• Physical Properties of Ethers
• Preparation of Ethers
• Reactions of Ethers
• Silyl Ethers as Protecting Groups
• Epoxides: Structure and Nomenclature
• Synthesis of Epoxides
• Reactions of Epoxides
• Ethylene Oxide and Epichlorohydrin: Building Blocks in Organic Synthesis
• Crown Ethers
3. Infrared Spectroscopy
• Electromagnetic Radiation
• Molecular Spectroscopy
• Infrared Spectroscopy
• Interpreting Infrared Spectra
• Solving Infrared Spectral Problems
4.  Nuclear Magnetic Resonance Spectroscopy
• Nuclear Spin States
• Orientation of Nuclear Spins in an Applied Magnetic Field
• Nuclear Magnetic Resonance
• An NMR Spectrometer
• Equivalent Hydrogens
• Signal Areas
• Chemical Shift
• Signal Splitting and the (n+1) Rule
• The Origins of Signal Splitting
• Stereochemistry and Topicity
• ¹³C-NMR
• The DEPT Method
• Interpretation of NMR Spectra
5. Organometallic Compounds
• Organomagnesium and Organolithium Compounds
• Lithium Diorganocopper (Gilman) Reagents
6. Aldehydes and Ketones
• Structure and Bonding
• Nomenclature
• Physical Properties
• Reactions
• Addition of Carbon Nucleophiles
• Keto-Enol Tautomerism
• Oxidation
• Reduction
• Reactions at an a-Carbon
7. Carboxylic Acids
• Structure
• Nomenclature
• Physical Properties
• Acidity
• Preperation of Carboxylic Acids
• Reduction
• Esterification
• Conersion to Acid Chlorieds
• Decarboxylation
8. Functional Derivatives of Carboxylic Acids
• Structure and Nomenclature
• Acidity of Amides, Imides, and Sulfonamides
• Characteristic Reactions
• Reaction with Water: Hydrolysis
• Reaction with Alcohols
• Reactions with Ammonia and Amines
• Reaction of Acid Chlorides with Salts of Carboxylic Acids
• Interconversion of Functional Derivatives
• Reduction
9. Enolate Anions and Enamines
   • Formation and Reactions of Enolate Anions
   • Aldol Reaction
   • Claisen Condensations
   • Reaction with Alcohols
10. Dienes, Conjugated Systems, and Pericyclic Reactions
    • Stability of Conjugated Dienes
    • Electrophilic Addition to Conjugated Dienes
    • Pericyclic Reaction Theory
    • The Diels-Alder Reaction
11. Benzene and the Concept of Aromaticity
• The Structure of Benzene
• The Concept of Aromaticity 
• Nomenclature
• Phenols
• Reactions at a Benzylic Position
12. Reactions of Benzene and It’s Derivatives
• Electophilic Aromatic Substitution 
• Disubstitution and Polysubstitution
• Nucleophilic Aromatic Substitution

2. Laboratory/Studio Sessions

1. Observing the Reaction Kinetics of Sucrose with Polarimetryl
2. Using a Gas Chromatograph: Identifying Unknown Compounds
3. Isolation and Epoxidation of a Natural Product: R-(+)-Limonene
4. Grignard Formation of Crystal Violet
5. IR Lab
6. NMR Lab
7. Structure Determination
8. Synthesis of Fluorescein
9. Synthesizing Ethyl Acetate by Fischer Esterification
10. Synthesis of Dibenzalacetone by Aldol Condensation
11. The Diels-Alder Reaction of Anthracene with Maleic Anhydride
12. Friedel-Crafts Acylation of Ferrocene
13. The Synthesis and Analysis of Aspirin