Organic Chemistry

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Chabot College
December, 1995
Replaced Fall 2006
Course Outline for Chemistry 12B
ORGANIC CHEMISTRY
Catalog Description:
12B - Organic Chemistry
5 Units
Continuation of Chemistry 12A with an introduction to the chemistry of aromatics,
amines, carbanions, carboxylic acids, aldehydes, ketones and biochemical topics focusing
on structure, synthesis, and mechanisms of reaction. Laboratory work in basic
techniques, synthetic methods, qualitative, spectroscopic, and chromatographic analysis
techniques. Designed for students whose interests require a full year in-depth study of
organic chemistry. Prerequisite: Chemistry 12A (completed with a grade of C or higher).
3 hours lecture, 6 hours laboratory.
Prerequisite Skills:
Upon entering the course, the student should be able to:
1. use a mechanistic approach to make reasonable predictions of major products formed
in reactions involving hydrocarbons, alkyl halides, alcohols, and ethers
2. explain physical and chemical properties of hydrocarbons, alkylhalides, alcohols, and
ethers
3. use spectroscopic data to elucidate structures for organic compounds
4. identify structural and optical isomers and correlate properties with structure
5. use IUPAC systems to name compounds of common functional groups
6. perform basic laboratory techniques in organic laboratory: crystallization, simple and
fractional distillation, extractions, microscale and macroscale syntheses,
chromatography, and spectroscopy analysis
7. follow safe practices in handling organic chemicals
Expected Outcomes for Students:
Upon completion of the course, the student should be able to:
1.
propose reasonable syntheses for compounds in the classes studied;
2.
use spectroscopic information and data concerning reactions or physical properties
to elucidate structures for compounds in the classes studied;
3.
draw mechanistic pathways which illustrate how the products are obtained from
the reactants;
4.
evaluate kinetic data as a tool in elucidating the mechanism for a reaction;
5.
name compounds of the classes studied;
6.
carry out syntheses in the laboratory, using techniques developed in Chemistry
12A to monitor the progress of the reaction and the purity of the product;
7.
identify an unknown organic compound in the laboratory by chemical methods
(optional, can be done in Chemistry 12B);
8.
utilize carbanions in proposing sophisticated syntheses;
9.
apply knowledge of organic reactions to biological processes;
10.
develop and work on a special research project (optional);
11.
make a formal oral and written presentation about a special research project
(optional).
Chabot College
Course Outline for Chemistry 12B, Page 2
December 1995
Course Content (Lecture):
I
II
III
IV.
V.
VI.
VII
Aromatics:
1. Review of aromaticity.
2. Reactions of benzene.
3. Electrophilic aromatic substitution mechanism, including reactivity and orientation.
4. Synthesis of substituted benzenes.
5. Electrophilic substitution in naphthalene.
Arenes and Their Derivatives:
1. Structure and properties.
2. Nomenclature.
3. Reactions of alkylbenzenes.
4. Preparation and reactions of alkenylbenzenes.
Aldehydes and Ketones:
1. Structure and properties.
2. Nomenclature.
3. Laboratory preparations of aldehydes and ketones.
4. Reactions of aldehydes and ketones.
5. Detailed analysis of nucleophilic addition.
6. Multi-step syntheses of aldehyes, ketones and related compounds.
Carboxylic Acids:
1. Structure and properties.
2. Nomenclature.
3. Acidity and relationship to structure.
4. Laboratory preparations of carboxylic acids.
5. Reactions of carboxylic acids.
Functional Derivatives of Carboxylic Acids:
1. Nucleophilic acyl substitution reactions.
2. Mechanism of nucleophilic acyl substitutions and comparison to alkyl nucleophilic
substitutions.
3. Structure, nomenclature, preparation and reactions of acid chlorides.
4. Structure, nomenclature, preparation and reactions of acid anhydrides.
5. Structure, nomenclature, preparation and reactions of amides.
6. Structure, nomenclature, preparation and reactions of esters.
Carbanion Chemistry:
1. Aldol condensations.
2. Claisen condensations.
3. Wittig reactions.
4. Malonic ester synthesis of carboxylic acids.
5. Acetoacetic ester synthesis of ketones.
6. Use of the above reactions in multi-step syntheses.
Alpha-beta unsaturated Compounds:
1. Structure and properties.
2. Laboratory preparations.
3. Electrophilic and nucleophilic addition reactions.
4. The Michael addition.
Chabot College
Course Outline for Chemistry 12B, Page 3
December 1995
VIII.
IX.
X
XI.
XII.
5. The Diels-Alder reaction.
Amines:
1. Structure and properties.
2. Nomenclature.
3. Structure and relationship to base strength.
4. Sterochemistry of nitrogen.
5. Laboratory preparations of amines.
6. Reactions of amines.
Phenols:
1. Structure and properties.
2. Nomenclature.
3. Structure and relationship to acid strength.
4. Laboratory preparations of phenols.
5. Reactions of phenols.
Aryl Halides:
1. Structure and properties.
2. Nomenclature.
3. Laboratory preparations of aryl halides.
4. Reactions of aryl haldies.
5. Detailed analysis of nucleophilic aromatic substitution reactions, including both
bimolecular displacement and elimination-addition mechanisms.
Heterocyclic Compounds:
1. Structure and properties of pyrrole, furan and thiophene and pyridine.
2. Electrophilic substitution in heterocyclic compounds.
3. Nucleophilic substitution in pyridine.
Biomolecules:
1. Carbohydrates;
a. Classifications, Fischer Projections and configurations.
b. Cyclic structures of monosaccharides, hemiacetal formation.
c. Monosaccharide anomers and mutarotation.
d. Reactions of monosaccharides (Kiliani-Fishcher synthesis and The Ruff
Degradation)
e. Disaccharides and polysaccharides.
2. Amino acids and Proteins;
a. Structure and properties of amino acids including isoelectric points.
b. Synthesis of alpha amino acids.
c. Peptide bonds.
d. Peptide sequencing (Edman Degradation and C-Terminal Residue Determination
Technique).
e. Peptide synthesis.
f. Proteins, structure and denaturation.
g. Enzymes.
3. Lipids;
a. Structure and properties of waxes, fats and oils.
b. Phospholipids, structure and use in cell membranes.
c. Structure and biosyntheses of terpenes and steroids.
Chabot College
Course Outline for Chemistry 12B, Page 4
December 1995
Course Content (Laboratory):
I.
II.
III.
Techniques:
1. Multi-step synthesis
2. Gas chromatography
3. Fourier-Transform Infrared Spectroscopy
4. Vacuum Distillation
Qualitative Analysis:
1. Wet chemistry analysis of unknowns including formation and purification of
derivatives for elucidating molecular structure.
2. Interpretation of IR and NMR spectra for elucidating molecular structures.
Library Research
Methods of Presentation:
1.
2.
3.
4.
Informal lecture with student questions encouraged.
Models, periodic tables, films, overlays.
Demonstrations.
Safety and proper respect for chemicals and scientific apparatus are
stressed.
Methods of Evaluating Student Progress:
1.
2.
3.
4.
Quizzes
Written lab reports
Midterm examinations
Final examination
Textbook(s) (Typical):
Organic Chemistry, Morrison and Boyd, Prentice Hall Publishers
Special Student Materials:
1. Molecular model kit
2. Safety goggles approved for Chemistry laboratory
3. Laboratory coat/apron
al
constantly
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