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Master Course Outline
CHEM& 263
Organic Chemistry w/Lab III
Course Description: This course is a continuation of CHEM& 262 for students desiring three quarters of
organic chemistry. FMO theory, nonclassical carbocations, heterocycles, rearrangements, amino acids,
lipids, carbohydrates, proteins and nucleic acids. 3 lecture hours. Satisfies specified elective requirement
for the AA degree.
Credits: 3
Prerequisites: A grade of “C-” or better in CHEM& 262 or instructor permission
Recommended Preparation: none
Co-requisites: none
Learning Outcomes:
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Aldehydes and ketones: nomenclature, structure and bonding of the carbonyl group, physical
properties, and sources
Reactions of aldehydes and ketones: nucleophilic addition, cyanohydrins formation, acetal
formation
Acetals as protecting groups
Reactions with primary and secondary amines
The Wittig reaction and alkene synthesis
Stereoselective addition to carbonyl groups
Oxidation of aldehydes
Steroscopic analysis of aldehydes and ketones
Carboxylic acids: nomenclature, structure and bonding, physical properties, and sources
Acidity of carboxylic acids; substituents and acid strength
Ionization of substituted benzoic acids
Dicarboxylic cids
Salts of carboxylic acids
Synthesis of carboxylic acids : by carboxylation of Grignard reagents, and preparation and
hydrolysis of nitriles
Reactions of carboxylic acids: acid catalyzed esterification, intramolecular ester
formation;lactones, decarboxylation of malonic acid and related compounds
Spectroscopic properties of carboxylic acids.
Carboxylic acid derivatives: nomenclature, structure and reactivity, and sources
General mechanism for Nucleophilic acyl substitution
Nucleophilic acyl substitution in acyl chlorides, acid anhydrides
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Acid catalyzed and base catalyzed ester hydrolysis
Reactions of esters with ammonia and amines, Grignard reagents, Lithium aluminum hydride
Amides: acid and base hydrolysis
Preparation and hydrolysis of nitriles
Addition of Grignard reagents to nitriles
Spectroscopic analysis of carboxylic acid derivatives
Enols and enolates: The Claisen condensation, acetoacetic ester synthesis, the malonic ester
synthesis
Amines: nomenclature, structure and bonding, and physical properties
Basicity
Tetraalkylammonium salts as phase-transfer catalysts
Reactions that lead to amines: alkylation of ammonia, the Gabriel synthesis
Lithium aluminum hydride reduction of an amide
Reductive animation
Reactions of amines: with alkyl halides, the Hofmann elimination
Electrophilic aromatic substitution in arylamines
Nitrosation of alkyl and arylamines
Synthetic transformations of aryl diazonium salts
Azo coupling
Spectroscopic analysis of amines
Phenols: nomenclature, structure and bonding, and physical properties, and sources
Acidity of phenols: substituent effect on acidity
Naturally occurring phenols
Reactions of phenols: electrophilic aromatic substitution, acylation, carboxylation
Preparation of aryl ethers from phenols
Cleavage of aryl ethers by hydrogen halides
Claisen rearrangement of allyl aryl ethers
Oxidation of phenols
Spectroscopic Analysis of phenols
Classification of carbohydrates
Fischer projections and D,L notation
Aldotetroses, aldopentoses, and aldohexoses
Cyclic forms of carbohydrates: furanose and pyranose forms
Mutarotation
Carbohydrate conformation: the anomeric effect
Ketoses
Deoxy sugars
Disaccharides
Polysaccharides
Amino acids, peptides and proteins
Classification of amino acids, stereochemistry, acid base behavior
Synthesis and reactions of amino acids
Some biochemical reactions of amino acids
Transamination
Introductory peptide structure determination
Amino acid analysis
Partial hydrolysis of peptides
End group analysis
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Amino group protection
Carboxyl group protection
Peptide bond formation
Secondary, tertiary and quaternary structures of polypeptides and proteins
Nucleosides, nucleotides, and nucleic acids
Pyrimidines, and purines
Phosphodiesters, oligonucleotides, and polynucleotides
Secondary and tertiary structure of DNA
Replication of DNA
Ribonucleic acids, Protein biosynthesis
AIDS
DNA sequencing
The human genome project
Synthetic polymers: some background, nomenclature, classification- chain growth and step
growth, and additon polymers
Chainbranching in free-radical polymerization
Branching in polyethylene by inter and intramolecular hydrogen transfer
Anionic and cationic polymerization
Polyamides, polyesters, polycarbonates, polyurethanes, and copolymers
Course Resources/Textbooks/Website:
These textbooks are required for this course as well as the beginning and second course of the
sequence, CHEM 261 and 262
Organic Chemistry, 8th Edition, Frances Carey and Robert Guiliano, McGraw Hill,
ISBN: 987-0-07-340261-1
Organic Chemistry Laboratory Manual, 3rd Edition, Anne Padías, Hayden McNeil, ISBN: 978-07380-3748-6
Making the Connection2, A How-To Guide for Organic Chemistry Lab Techniques, Anne Padías,
Hayden McNeil, ISBN: 978-1-4292-8812-5
Students are also required to purchase an Organic Chemistry Laboratory Notebook, Hayden
McNeil,
ISBN: 978-1-930882-46-1
Other ancillary materials are available from the publisher such as Student Solution Manual,
which is recommended but optional. If you have questions about the text, please contact Julie
Nelson at jnelson@ghc.edu.
A molecular model kit is also highly recommended
These items are all available at the GHC Bookstore.
Academic Integrity: All forms of cheating, falsification, and plagiarism are against the rules of this course
and of Grays Harbor College. Students who are unsure what constitutes academic dishonesty are
responsible for asking the instructor for clarification. Instances of intentional academic dishonesty will
be dealt with severely.
Disabilities: Students who have documented disabilities that require accommodations in compliance
with the Americans with Disabilities Act should contact the Disability Support Services coordinator as
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well as the instructor of the course in order to ensure that together we create an optimal environment
for educational achievement.
W Day, the final day to officially withdraw from a course, is the Thursday of the seventh week (Thursday
of the fourth week for summer quarter). Students who do not withdraw by that date will receive the
grades they have earned, regardless of whether they are attending the course or completing the work.
Students who are considering withdrawal are strongly advised to consult with the instructor, advisor and
financial aid prior to withdrawing. The only withdrawals allowed after W Day are complete withdrawals
from all courses.
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