Chabot College
December, 1995
Replaced Fall 2006
Course Outline for Chemistry 12A
ORGANIC CHEMISTRY
Catalog Description:
12A - Organic Chemistry
5 Units
Hydrocarbons, alkyl halides, alcohols, ethers, and an introduction to aromatic
hydrocarbons. Structure, bonding, stereochemistry, conformational analysis
nomenclature, and physical properties in relation to these particular groups of
compounds. Emphasis on reactivity, and reaction mechanisms. Laboratory work
includes microscale, macroscale, spectroscopic, and chromagraphic techniques.
Chemistry 12A is the first semester in a year course in organic chemistry designed for
students majoring in chemistry and related disciplines. Prerequisites: Chemistry 1B
(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. construct electron configurations and draw Lewis structures given chemical formulas
2. determine molecular shapes using VSEPR and hybrid orbital theories
3. generate and evaluate resonance structures in terms of contribution and overall
structure
4. determine limiting reagent and calculate percent yield
5. describe properties of liquids, solids, and solutions
6. interpret chemical reactions via thermodynamic data
7. use molecular geometries to determine intermolecular forces
8. interpret redox reactions
9. determine if reaction mechanisms fit experimental rate laws
10. use acid-base theory to predict reaction products and extent of reaction
Expected Outcomes for Students:
Upon completion of 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 groups studied based on structural
analysis;
3. use spectroscopic data to elucidate structures for organic compounds;
4. Identify structural and optical isomers and correlate properties with structure;
5. Name compounds of the classes studied;
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.
Course Content (Lecture):
I.
Review of General Chemistry Concepts:
Chabot College
Course Outline for Chemistry 12A, Page 2
December 1995
II.
III.
IV.
V.
VI.
VII.
1. Atomic structure and electron configurations.
2. Bonding, hybrid orbitals and molecular shapes.
3. Molecular structure and relationship to physical properties (boiling point, solubility,
etc).
4. Acid/base theories.
5. Determination of empirical and molecular formulas from quantitative analysis.
Overview of Organic Chemistry:
1. Structure of major functional groups including hydrocarbons, alkyl halides, alcohols,
ethers, carbonyl compounds, amines and amides.
2. Nomenclature of above functional groups.
Alkanes:
1. Structure and physical properties.
2. Sources of alkanes and industrial preparations.
3. Laboratory preparations of alkanes.
4. Reactions of alkanes including free radical halogenation.
5. Detailed analysis of use of kinetics and mechanisms.
6. Conformational analysis of open chain alkanes.
7. Structure of cycloalkanes, including stability and conformational analysis.
8. Stereochemistry of cycloalkanes.
9. Preparation and reactions of cycloalkanes.
10. Carbenes and cycloaddition reactions.
Stereochemistry:
1. Polarimetry and optical activity.
2. Chiral carbons and chiral substances.
3. Enantiomers, diastereomers and racemic modifications.
4. Specification of configuration, R/S.
5. Synthesis and optical purity.
6. Stereospecific reactions.
7. Stereoselectivity vs. stereospecificity.
Alkyl Halides:
1. Structure and physical properties.
2. Laboratory preparations of alkyl halides.
3. Reactions of alkyl halides.
4. Detailed analysis of nucleophilic substitution reactions (SN1 and SN2 mechanisms).
5. Solvent effects and secondary bonding.
6. Carbocations and rearrangements.
Alcohols:
1. Structure and physical properties.
2. Industrial sources.
3. Laboratory preparations of alcohols.
4. Reactions of alcohols.
5. Multi-step synthesis.
Ethers:
1. Structure and physical properties.
2. Laboratory preparation of ethers.
3. Reactions of ethers.
4. Cyclic ethers and epoxides.
Chabot College
Course Outline for Chemistry 12A, Page 3
December 1995
VIII.
IX.
X.
XI.
XII.
5. Crown ethers.
Spectroscopy:
1. Mass Spectroscopy and use in determining molar mass and molecular formulas.
2. Infrared Spectroscopy and use in elucidating molecular structures.
3. Nuclear Magnetic Resonance (1H and 13C) and use in elucidating molecular
structures.
Alkenes:
1. Structure and properties.
2. Geometric Isomerism including specification of E/Z configurations.
3. Laboratory preparations of alkenes.
4. Detailed analysis of elimination reactions (E1 and E2 mechanisms).
5. Stereochemistry of E2 reactions, syn- and anti-elimination.
6. Competition between elimination and substitution.
7. Reactions of alkenes.
8. Detailed analysis of addition reactions (electrophilic and free radical).
9. Stereochemistry of addition reactions, syn- and anti-addition.
10. Free radical addition and substitution in alkenes including allylic rearrangements.
Dienes:
1. Structure and properties.
2. Resonance theory and stability of dienes.
3. Electrophilic addition to conjugated dienes; 1,4-addition.
4. Kinetic vs. thermodynamic products (1,2- vs. 1,4-addition).
5. Polymerization of dienes.
6. Isoprene and the isoprene rule.
Alkynes:
1. Structure and properties.
2. Laboratory preparation of alkynes.
3. Reactions of alkynes (including introduction of tautomerism via hydration).
4. Acidity of alkynes.
Aromaticity:
1. Benzene; structure and resonance.
2. Aromatic character; the Huckel 4n+2 rule.
3. Polynuclear aromatic substances.
Course Content (Laboratory):
I.
Techniques:
1. Boiling Point and Melting Point Determination
2. Extraction
3. Simple and Fractional Distillation
4. Polarimetry
5. Crystallization
6. Thin layer and column chromatography
8. Refractometry
9. Vacuum Sublimation
10. Infrared Spectroscopy
Chabot College
Course Outline for Chemistry 12A, Page 4
December 1995
II.
Safety:
1. Correct handling of organic compounds.
2. Use of literature (Reference books such as Merch Index, etc and MSDS sheets) to
determine possible hazards.
Methods of Presentation:
1. Lecture and class discussions
2. Models, computerized molecular modeling, videos, and transparencies
3. Demonstrations
4. Hands-on laboratory work to learn lab techniques and support lecture topics
Methods of Evaluating Student Progress:
1.
2.
3.
4.
Quizzes
Midterm examinations
Final Exam
Written lab reports and lab notebooks
Textbook(s) (Typical):
Organic Chemistry, Morrison and Boyd, Prentice Hall Publishers
Introduction to Organic Laboratory Techniques, a Microscale Approach, Parra,
Lampman, Kriz, and Engel, Saunders College Publishers
Special Student Materials:
1. Molecular model kit
2. Safety goggles approved for chemistry laboratory
3. laboratory coat/apron
DG/al