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:

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:

Construct and name structural formulas for alcohols, ethers, epoxides, aldehydes, ketones, carboxylic acids, acid halides, acid anhydrides, amines, imides, esters, salts of carboxylic acids, substituted benzenes and phenols.  MnTC Goal 3

Predict the products for the reaction of HX with alcohols.  MnTC Goal 3

Design experimental procedures and perform in the laboratory the synthesis an alcohol from an alkene.  MnTC Goal 3

Propose reactants and reagents for the preparation of ethers using the Williamson Ether Synthesis reaction, as well as, stating the limitations.  MnTC Goal 3

Draw the mechanism for the acid catalyzed dehydration of alcohols.  MnTC Goal 3

Predict the products from nucleophilic ring opening reactions of ethylene oxide.  MnTC Goal 3

Assign infrared spectra to molecular structures.  MnTC Goal 3

Analyze and interpret NMR spectra in order to deduce structural formulas.  MnTC Goal 3

Draw a generic mechanism for nucleophilic addition to a carbonyl group.  MnTC Goal 3

Propose reactants and reagents for the preparation of alkenes using the Wittig reaction.  MnTC Goal 3

Predict the products for reduction reactions of alkenes, aldehydes, ketones and carboxylic acids.  MnTC Goal 3

Propose an appropriate haloalkane for the preparation of a carboxylic acid using carbon dioxide and a Grignard reagent.  MnTC Goal 3

Perform retrosynthetic analysis to interconvert carboxylic acids, acid anhydrides, esters and amides.  MnTC Goal 3

Apply the Huckel criteria to cyclic structures to determine aromaticity.  MnTC Goal 3

Predict the effects of a substituent group on further substitution in electrophilic aromatic substitution reactions.  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. 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