Riverside Community College District
Integrated Course Outline of Record
Chemistry 12A
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COURSE DESCRIPTION
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12A Organic Chemistry I
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Units: 5.00
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Prerequisite(s):
CHE 1B: General Chemistry II
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A discussion of aliphatic hydrocarbons that focuses on their structure, reactivity, methods of synthesis, physical properties, and reaction mechanisms. Laboratory work emphasizes techniques used to identify, separate, and purify substances. 54 hours lecture and 108 hours of laboratory.
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SHORT DESCRIPTION FOR CLASS SCHEDULE
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Structure and reactivity of the compounds of carbon for pre-professional programs and science majors.
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ADVISORY ENTRY SKILLS
None.
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STUDENT LEARNING OUTCOMES
Upon successful completion of the course, students should be able to:
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1. Identify the factors affecting the structure, physical properties,
and chemical reactivity of the aliphatic hydrocarbons.
2. Apply the reactions, methods of preparation and nomenclature for
each of the families of reactions studied.
3. Perform basic laboratory operations used to measure physical
properties, purify organic substances, and separate mixtures.
4. Setup and carry out a synthetic operation through the final
purification.
5. Analyze infrared and nuclear (proton) magnetic resonance to
determine structures of organic molecules.
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COURSE CONTENT
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TOPICS
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The structure of the course will depend upon the preferences of the instructor whether to adhere to a functional group or mechanistic approach and whether the front-end conceptual materials is done early, by topic, or interspersed throughout the course. Thus individual concepts from the list below may or may not be included under the heading where they are listed, but the lectures and/or laboratories contain the following content:
1. Review
a. Atomic structure
b. Atomic properties
c. Molecular geometry
2. Bonding theories
a. Valence bond model
b. Molecular orbital theory
3. Structure
a. Lewis structures
b. Resonance
c. Three dimensional representation
d. Potential surface, minima (local and global), saddle points
c. Hybridization
4. Molecular conformation
a. Angle and torsion strain
b. Staggered and eclipsed conformations of simple hydrocarbon
molecules
c. Chair and boat conformations of cyclohexane rings
D. Relief of strain in cyclic hydrocarbon rings having three through
seven ring atoms
5. Chemical Thermodynamics
a. Heats of combustion and hydrogenation
b. Relative stabilities
6. Chemical Kinetics
a. Transition states and activation energy
b. Rate laws and reaction order
c. 1st and 2nd order reactions
7. Stereochemistry
a. Chirality and optical activity
b. Enantiomers, diastereomers, and meso compounds
c. EZ (cis/trans) isomerism
d. Effect of stereo environment on reaction outcomes
8. Acid Base
a. Bronsted acidity, weak and strong acids
b. Conjugate acid/bases and leveling effect
c. Acid strength and pK
d. Lewis acidity
e. Alcohols as acids and bases
f. Hydrocarbons as acids
9. Classes of reactions
a. Addition reactions
b. Elimination reactions
c. Substitution reactions metallation
10. Mechanisms
a. Electrophilic addition
b. SN1 and SN2 Nucleophilic substitution
c. E1 and E2 substitution
d. Free radical substitution
11. Reactive intermediates: in all cases below, the structure of each
intermediate, means of formation, relative stabilities, and
methods of quenching/decomposition will be discussed.
a. Carbenium ions (carbocations)
b. Carbanions
1. Free readicals
12. Families of compounds: for each family studied, the student will
know the nomenclature, physical properties, methods of
synthesis, and important reactions
a. Alkanes
b. Alkynes
c. Organosulfur compounds
d. Alcohols/ethers
e. Organohalogen compounds
13. Carbon-carbon bond forming reactions
a. Organometalic/organohalogen coupling
b. Oxirane metalation
c. Acetylide alkylation
14. Special topics:
a. Terpene
b. Biosynthetic formation of the terpenes
c. Cellular substitution reactions
d. Conformation in fused ring systems
15. Physical properties
a. Melting points
b. Boiling points
c. Index of refraction
16. Methods of separation and purification
a. Extraction
b. Distillation
c. Crystallization
17. Synthetic methods
a. Temperature control
b. Micro and semi microscale reactions
c. Workup
d. Final purification
18. Qualitative analysis
a. Methods for identifying elements
b. Simple tests to distinguish between hydrocarbons
19. Spectroscopy
a. Infrared spectroscopy
b. Interpretation of spectroscopy
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METHODS OF INSTRUCTION
Methods of instruction used to achieve student learning outcomes may include, but are not limited to:
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- Traditional lecture: information transfer, problem-solving approaches and strategies, applications
- Multimedia Presentation: information transfer, problem-solving approaches and strategies, applications
- Socratic interaction
In-class problem solving with instructor assistance
- Instructor guided collection, calculation, and analysis of data from experimental procedures
- Small Group Activities
- Computer Aided Instruction (including tutorials), molecular modeling, internet assignments
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METHODS OF EVALUATION
Students will be evaluated for progress in and/or mastery of learning outcomes by methods of evaluation which may include, but are not limited to:
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- Exams and quizzes testing for problem solving ability, knowledge of concepts and reactions, and the ability to apply the concepts
- Oral reports
Written assignments
- Laboratory reports
- Laboratory projects and/or performance through assessment of purity, yields, or correct identification of unknowns
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ASSIGNMENTS
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Required Reading Assignments
Required Writing Assignments
Other Outside-of-Class Assignments
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COURSE MATERIALS
All materials used in this course will be periodically reviewed to ensure that they are appropriate for college level instruction. Possible texts include:
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Brown and Foote. Organic Chemistry. 3 ed.
any: Saunders College Publishing, 2000.
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Bruice. Organic Chemistry. 2 ed.
any: Prentice Hall, 1998.
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Pavia, Lampman, Kriz, and Engel. Organic Laboratory Techniques – A Microscale Approach. 3 ed.
any: Thomson Brooks Cole, 1999.
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| 05/04 |
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