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.

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:

Name of Institution	Course Number and Title	Credits
St. Cloud State University	CHEM 311 Organic Chemistry 2	4
Bemidji State University	CHEM 2312 Organic Chemistry II	3
Bemidji State University	CHEM 2372 ORGANIC CHEMISTRY LABORATORY II	1

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.
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:

Expected Outcome	MnTC Goal Area
solve chemistry related problems using experimental or simulated data.	3
use the scientific method to formulate and test hypothesis and scientific laws.	3
relate chemical principles to the real world.	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. Benzene and the Concept of Aromaticity
• The Structure of Benzene
• The Concept of Aromaticity 
• Nomenclature
• Phenols
• Reactions at a Benzylic Position
10. Reactions of Benzene and It’s Derivatives
• Electophilic Aromatic Substitution 
• Disubstitution and Polysubstitution
• Nucleophilic Aromatic Substitution

2. Laboratory/Studio Sessions

1. Cyclohexene From Cyclohexanol
2. Conversion of t-Amyl Alcohol to t-Amyl Chloride Using HCl
3. Conversion of Acetominophen into Phenacetin
4. Steam Distillation of Orange Oil
5. IR Lab
6. NMR Lab
7. Structure Determination
8. Oxidation of Heptanal to Heptanoic Acid Using Potassium Permanganate
9. Reduction of Vanillin Using NaBH4
10. Synthesis of Fluorene-9-Carboxylic Acid
11. Synthesis of Aspirin by Acetylation
12. Synthesis of Banana Fragrance of Salicylic Acid
13. Oxidation of p-Nitrotoluene to p-Nitrobenzoic acid Using Na2Cr2O7