Course Outline: Organic Chemistry II (CHM271)

NOTE on Laboratory: Both Lecture and Laboratory must be taken simultaneously; separate grades will not be given for either. Students must pass the laboratory section to receive a passing grade in the entire course.

Semesters Offered: Fall, Spring, & Summer

Prerequisites: CHM 270 or equivalent with a grade of C- or higher

Catalog Course Description:

A continuation of CHM 270. Topics covered include: alkyl and aryl halides, alcohols and phenols, ethers and epoxides, carboxylic acids, esters, anhydrides, aldehydes, ketones, amines, amino acids, carbohydrates, heterocycles and polymers.

Required Course for:           Certificate for Health Professions

Elective Course for:             Bioscience; Science, Technology, & Society; Liberal Arts & Sciences

Course Texts: 

Organic Chemistry (Wade,  9^th Edition, Pearson)

Organic Chemistry Laboratory Manual CHM 271 (FSC Chemistry Dept.)

Other Required Course Materials

Calculator, laboratory coat and safety glasses or goggles.

Course Learning Objectives:

I. Nuclear Magnetic Resonance Spectroscopy

Theory of nuclear magnetic resonance, principles of chemical shift,  signal splitting, signal integration, chemical shift, effects of symmetry

At the end of this section, the student should be able to:

1. Interpret  ¹H and ¹³C NMR Spectra.
2. Intepret the chemical shift of signals.
3. Be able to solve unknown structures using ¹H and ¹³C NMR.
4. Intepret splitting patterns in ¹H NMR.

II. Reactions of Alcohols

Structures, nomenclature, physical properties, preparations, chemical  reactions, mechanisms 

At the end of this section, the student should be able to:

1. Draw the general structure of an alcohol.
2. Name alcohols by the IUPAC system.
3. Propose methods of synthesis.
4. Predict the products of reactions of alcohols.
5. Explain the importance of reaction conditions on class of product formed.
6. Formulate mechanism of reactions of alcohols.

III. Ethers, Epoxide, Thioethers

Structure, nomenclature, physical properties, preparations, chemical reactions, mechanisms 

At the end of this section, the student should be able to:

1. Give the structure of a ether, epoxide and thioether.
2. Name said functional groups by the IUPAC system.
3. Propose methods of synthesis for said functional groups.
4. Predict the products of reactions of ether, epoxide and thioethers.
5. Synthesize ethers, epoxides and thioethers.
6. Formulate mechanisms of reactions of ethers, epoxides and thioethers.

IV. Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Structure, nomenclature, physical properties, preparations, chemical reactions, mechanisms, and molecular orbital theory..

At the end of this section, the student should be able to:

1. Draw the molecular orbitals of a conjugated system.
2. Complete 1,2 vs. 1,4 addition reactions.
3. Interpret the electronic configurations of allylic radicals, cations, and anions.
4. Describe and apply the Diels-Alder reaction.
5. Interpret UV-Vis and how it can be used to analyze conjugated compounds. .

V. Aromatic Compounds

Structure, nomenclature, physical properties, molecular orbital theory, spectroscopy of benzene and disubstituted benzenes

At the end of this section, the student should be able to:

1. Provide the general structure and physical properties of benzene.
2. Interpret the molecular orbital theory of benzene.
3. Apply Huckel’s rule to determine aromaticity (aromatic, anti-aromatic, and nonaromatic). 
4. Apply aromaticity and mechanism to heterocyclic aromatics.
5. Apply aromaticity and mechanism to polynuclear aromatic compounds.
6. List the physical properties of benzene and its derivatives.
7. Interpret NMR spectra of aromatic compounds

VI. Reactions of Aromatic Compounds

Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms and synthesis.

At the end of this section, the student should be able to:

1. Describe and draw Electrophilic Aromatic Substitution (EAS).
2. Describe and apply the use of directing groups in EAS reactions.
3. Describe and draw Nucleophilic Aromatic Substituion (NAS).
4. Describe Benzyne Chemistry.
5. Describe and draw the side-chain reactions of Benzene derivatives.

VII. Ketones and Aldehydes

Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms and spectroscopy.

At the end of this section, the student should be able to:

1. Give the general structure of a ketone or aldehyde.
2. Name ketones and aldehydes by the IUPAC system and the common system.
3. Draw structures for ketones and aldehydes from the common or IUPAC name.
4. Explain the reactions of ketones and aldehydes.
5. Synthesize ketones and aldehydes.
6. Formulate mechanisms for the formation of ketones and aldehydes.
7. Interpret NMR spectra of ketones and aldehydes.

VIII. Amines

Structures, nomenclature, physical properties, preparation, chemical reactions, mechanisms, acidity and spectroscopy

At the end of this section, the student should be able to:

1. Give a general structure for an amine.
2. Name amines by the IUPAC system.
3. Rank compounds in order of increasing acidity.
4. Predict the product of reactions for amines. 
5. Formulate mechanisms for the formation of amines.
6. Use amines in synthetic sequences.

IX. Condensations and Alpha Substitutions of Carbonyl Compounds

Structures, physical properties, preparation, chemical reactions, mechanisms, condensation reactions and synthesis.

At the end of this section, the student should be able to:

1. Identify and give mechanism for the formation of enols and enolates.
2. Provide reaction mechanisms for condensation reactions.
3. Understand mechanism and be able to utilize the malonic ester and acetoacetic ester syntheses. 
4. Formulate mechanism for conjugate addition reaction to alpha-beta unsaturated ketones and aldehydes.
5. Apply the Robinson Annulation.
6. Utilize Reactions in multi-step synthesis.

X. Carboxylic Acids

Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms, synthesis and basicity.

At the end of this section, the student should be able to:

1. Write a general structure for a carboxylic acid.
2. Name carboxylic acids by the IUPAC system.
3. Draw structures of carboxylic acids corresponding to given names.
4. Predict the acidity of carboxylic acids.
5. Understand reaction Mechanisms for the formation of carboxylic acids.
6. Utilize carboxylic acids in multistep synthesis.
7. Interpret the spectroscopy of carboxylic acids.
8. Synthesize carboxylic acid derivatives from carboxylic acids.

XI. Carbohydrates and Nucleic Acids

Definition and classifications, aldoses, ketoses, structural determination, cyclic structure, polysaccharides.

At the end of this section, the student should be able to:

1. Classify carbohydrates.
2. Identify monosaccharides as D or L.
3. Draw monosaccharides in the Fischer, Haworth and Chair conformation projections.
4. Predict   the   products of reactions of monosaccharides.
5. Predict   the   products of reactions of disaccharides.
6. Deduce the structure of disaccharides.
7. Define the terms monosaccharide, disaccharide, reducing sugar, nonreducing sugar, anomeric center, furanose ring, pyranose ring and glucosides.
8. Explain the mechanism of cyclization reactions. 
9. Explain the difference between starch and   cellulose.

Laboratory Schedule

Experiment #                                           Title

1.                                                        Preparation of Aniline (Part 1)
2.                                                        Preparation of Aniline (Part 2)
3.                                                        Preparation of Acetanilide
4.                                                        Preparation of p-bromoacetanilide
5.                                                        Extraction and Purification of a Two Component Mixture
6.                                                        Purification of Extracts
7.                                                        Identification of a mixture by physical and spectroscopic analysis
8.                                                        Chemical Properties of Unknowns
9.                                                        Derivatives I (aldehyde or ketone)
10.                                                        Derivatives II (other functional groups)
11.                                                        Identification of Chemical Unknowns (Part 1)
12.                                                        Identification of Chemical Unknowns (Part 2)