Download Course Content (Laboratory)

Replaced Fall 2010
Fall 2008
Chabot College
Course Outline for Chemistry 8
SURVEY OF ORGANIC CHEMISTRY
Catalog Description:
8 – Survey of Organic Chemistry
6 units
Fundamental aspects of the structure, physical properties, chemical reactivity and synthesis of organic
compounds with emphasis on topics of interest to students in the biological sciences. Laboratory
experiments cover basic organic laboratory techniques using reactions or processes found in the
biological sciences. Chemistry 8 is a one-semester course in Organic Chemistry designed for students
majoring in biological sciences. No credit will be given for Chemistry 8 if taken after Chemistry 12A/B.
Prerequisite: Chemistry 1B (completed with a grade of “C” or higher). 4 hours lecture, 1 hour discussion,
3 hours laboratory.
Sally Jahnke [Typical contact hours: lecture 70, discussion, 17.5, laboratory 52.5]
Prerequisite Skills:
Upon entering the course, the student should be able to:
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solve problems involving gas phase equilibria;
determine the extent of acid-base, precipitation and complex equilibria;
interpret reactions in terms of Arrhenus, Bronsted-Lowry and Lewis acid-base theory;
predict whether oxidation-reduction reactions will occur and set up voltaic and electrolytic cells;
describe factors that affect the rate of chemical reactions and match mechanism with reaction
rates;
describe current models for the bonding of coordination compounds;
perform problems involving complex ion equilibria;
describe changes that occur in the nucleus of atoms;
identify organic compounds and simple isomers;
analyze properties of family groups of the periodic table in terms of chemical principles;
perform titrimetric experiments;
measure pH with the use of pH meter or indicators;
perform quantitative laboratory experiments in an accurate and precise manner;
perform qualitative analysis of anions and cations in the laboratory;
collect and analyze scientific data, using statistical and graphical methods;
use a visible spectrophotometer;
perform laboratory experiments in an efficient, safe, and purposeful manner.
Expected Outcomes for Students:
Upon completion of the course, the student should be able to:
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explain physical and chemical properties of common organic functional groups based on structural
analysis;
name compounds containing common functional groups using the IUPAC system of nomenclature;
predict major organic products for reactions involving functional groups studied;
give simple mechanisms for the following reaction types (SN1, SN2, E1, E2, electrophilic addition
and nucleophilic addition);
use spectroscopic data to elucidate structures for simple organic compounds;
identify structural and stereochemical isomers and correlate properties with structure;
propose short synthetic pathway to compounds of the functional groups studied;
apply knowledge of organic molecules to biological processes;
Chabot College
Course Outline for Chemistry 8, Page 2
September 2008
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perform basic laboratory techniques in organic laboratory such as but not limited to
(crystallization, distillation, extraction and chromatography techniques, polarimetry);
follow safe practices in handling organic chemicals.
Course Content (Lecture):
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Review of General Chemistry concepts
a. Atomic structure and electronic configurations
b. Bonding concepts, including: Lewis dot structures, hybridization, molecular geometries,
polarity, and molecular orbital theory
c. Intermolecular forces, and predicting physical properties (boiling point, etc) based on
molecular structure
d. Acid/Base properties, pH, and molecular structure; acid/base equilibria
Overview of organic chemistry
a. Structure of the most common functional groups including alkanes, alkenes, alkynes, alkyl
halides, aromatic hydrocarbons, alcohols, ethers, epoxides, amines, carboxylic acids, esters,
amides, acid halides, nitriles, acid anhydrides, aldehydes, and ketones.
b. Representation of the structure of organic molecules using expanded and condensed (Kekulé
or skeletal) structures and simple three-dimensional representations.
c. Common names of alkanes, alkyl halides, alcohols, amines and ethers using common alkyl
group names.
d. Introduction to reactivity concepts such as curved arrows, nucleophile, electrophile, etc.
Alkanes
a. Structure, representations and physical properties.
b. Sources of alkanes and industrial roles
c. IUPAC nomenclature and common names of alkanes, cycloalkanes, and alkyl halides
d. Structural (constitutional) isomerism in alkanes, cycloalkanes and alkyl halides.
e. Conformations of simple alkanes such as ethane and butane; Newman projections and
relative stability of conformations.
f. Reactivity of alkanes: Free radical halogenation (FRH)
g. Mechanism of FRH reactions
h. Free radical stability and product yield prediction in FRH reactions
Alkenes and alkynes
a. Structure and physical properties of alkenes and alkynes
b. IUPAC nomenclature of alkenes and alkynes; common names.
c. Geometric isomerism of alkenes; cis/trans and E/Z system nomenclature
d. Addition reactions of alkenes, such as hydrohalogenation, acid-catalyzed hydration, acidcatalyzed alcohol addition, halogenation, and catalytic hydrogenation
e. Addition Reactions of alkynes, including hydrohalogenation, hydration, and hydrogenation
f. Mechanisms of Markovnikov additions.
g. Carbocation stability
h. Relative stability of alkenes based on degree of alkyl group substitution
i. Simple synthetic preparations starting with alkenes or alkynes
Conjugated Organic molecules and Aromaticity
a. Review of resonance structures in organic molecules
b. Analysis of molecular stability based on resonance
c. Effect of delocalization of electrons on acidity/basicity.
d. Structure and molecular orbitals of benzene
e. IUPAC nomenclature of benzene derivatives
f. Definition of aromaticity
g. Electrophilic aromatic substitution (EAS) reactions of benzene and derivatives such as
catalytic halogenation, nitration, and Friedel-Crafts reactions
h. Mechanisms of EAS reactions
i. Simple synthetic preparations using EAS reactions
Chabot College
Course Outline for Chemistry 8, Page 3
September 2008
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Stereochemistry
a. Chirality and asymmetric centers in organic molecules
b. Optical activity
c. Representation of chiral molecules in three dimensions
d. R/S system of nomenclature of chiral molecules
e. Meso compounds and diastereomers
Reactions of Alkyl Halides
a. Nucleophillic Substitution (SN) Reactions: mechanism, kinetics and energetics
b. Stereochemistry of SN reactions
c. Eliminations reactions: mechanism, kinetics and energetics
d. Synthetic preparations using SN reactions
Alcohols
a. Structure and physical properties
b. IUPAC nomenclature of alcohols
c. Uses and Sources of alcohols
d. Substitution reactions of alcohols, with mechanism
e. Elimination reactions of alcohols, with mechanism
f. Oxidation reactions of alcohols.
g. Synthetic pathways from alcohols to other functional groups
Ethers and epoxides
a. Structure and physical properties of ethers
b. IUPAC nomenclature of ethers and epoxides
c. Reactions of ethers such as acid cleavage.
d. Simple ring-opening reactions of epoxides
e. Use of epoxides in synthesis
Amines
a. Structure and physical properties of amines
b. Basicity of amines
c. IUPAC nomenclature of amines
d. Acid/base reactions of amines
Carboxylic acids and Derivatives
a. Structure and physical properties of carboxylic acids, esters, amides, acid chlorides, and
nitriles
b. IUPAC nomenclature of carboxylic acids, esters, amides, acid chlorides, and nitriles
c. Acid/base reactions of carboxylic acids
d. Nucleophilic acyl substitution (NAS) reactions, including mechanism of non-acid catalyzed
types.
e. Relative reactivity of stated functional groups in NAS reactions
f. Hydrolysis reactions
Aldehydes and ketones
a. Structure and physical properties of aldhydes and ketones
b. IUPAC nomenclature of aldehydes and ketones
c. Carbonyl addition reactions of aldehydes and ketones: Grignard reactions, reduction
reactions, imine formation, hemiacetal, acetal, hemiketal and ketal formation reactions.
d. Relative reactivity of aldehydes and ketones
e. Synthesis using Grignard reagents and reducing reagents such as NaBH 4 and LiAlH4
Spectroscopic analysis of organic molecules
a. Proton nuclear magnetic spectroscopy of simple organic molecules
b. Use of infrared spectrophotometry in the identification of organic functional groups
c. Conjugation and ultraviolet/visible spectrophotometry
Carbohydrates
a. Structure, stereoisomerism, and classification of monosaccharides
b. Fischer and Haworth projections of monosaccharides
c. Structure and classification of common dissacharides
Chabot College
Course Outline for Chemistry 8, Page 4
September 2008
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d. Structure and classification of polysaccharides
e. Types of glycosidic linkages in oligiosaccharides
f. Reducing and nonreducing sugars
Amino acids and proteins
a. Structure, abbreviations, and classification of common amino acids
b. pH-dependent ionic forms of amino acids
c. Methods of amino acid separation; electrophoresis, isoelectric points
d. The peptide bond and structure of polypeptides
e. Types of protein structure: primary, secondary, tertiary, quartenary
f. Functional variety of proteins: enzymes, structural proteins, etc.
g. Simple primary structure determination of oligiopeptides using cleavage reagents
Lipids
a. Structure and classification of lipids:
1) fatty acids
2) fats and oils
3) waxes
4) triglycerides and phospholipids
5) terpenes
6) steroids
b. Hydrolysis of complex lipids
c. Biological functions of lipids such as lipid bilayers
Nucleic Acids
a. Structure of the purine and pyrimidine bases in RNA and DNA
b. Structure of nucleosides and nucleotides in RNA and DNA
c. Structure of polynucleotides, diphosphoester linkages
d. Base-pairing in the DNA double helix;
e. DNA replication, and sense/antisense sequences
Course Content (Laboratory):
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Laboratory Techniques
a. Extraction
b. Distillation
c. Chromatography
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Thin Layer
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Column
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Gas
d. Polarimetry
e. Refractometry
f. Melting point determination
g. Boiling point determination
h. Crystallization
i. Infrared Spectrophotometry
j. Synthesis of simple compounds
Recording and interpreting laboratory data
Laboratory Safety
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Handling of chemicals
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Researching safety of chemicals
c. Disposal of chemicals
Use of the scientific literature and reference material to research chemical properties.
Methods of Presentation:
1. Lecture and class discussions
Chabot College
Course Outline for Chemistry 8, Page 5
September 2008
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Exercises in problem solving
Models, computerized molecular modeling, videos and presentation slides
Demonstrations
Hands-on laboratory work to learn lab techniques and to support lecture topics
Assignments and Methods of Evaluating Student Progress:
1. Typical Assignments
a. Read the chapter on carboxylic acids and derivatives in your text and work the following
problems at the end of the chapter: 1,2,5,7,9,10,14-16,18,20-22,26,27,37a,d.
b. Synthesize banana oil using isopentyl alcohol and acetic acid;
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Purify the product by distillation
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Collect an infrared spectrum of your product to determine its purity.
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Determine the percent yield and percent recovery of your product.
2. Methods of evaluating student progress
a. Homework assignments
b. In-class and online problem sets
c. Quizzes
c. Written laboratory reports based on departmentally approved experiments
d. Written laboratory notebooks
e. Midterm examinations
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Final examination
Textbook(s) (Typical):
Essential Organic Chemistry, P.Y. Bruice, Prentice Hall, 2006
Fundamentals of Organic Chemistry, J. McMurry, Thomson, Brooks/Cole, 2006
Special Student Materials:
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Molecular model kit
Safety goggles approved for chemistry laboratory
Laboratory notebook
Scientific Calculator
Laboratory coat/apron
September 10, 2007
Andrew Wells