Chabot College
Fall 2006
Replaced Fall 2010
Course Outline for Chemistry 12A
ORGANIC CHEMISTRY I
Catalog Description:
12A - Organic Chemistry I
5 Units
The structure, nomenclature, bonding, stereochemistry, conformational analysis, and physical properties
in relation to alkanes, alkyl halides, alkenes, alkynes, alcohols, and ethers. Emphasis on reactivity and
reaction mechanisms. Multi-step synthesis is also introduced. Laboratory work includes microscale, semimicroscale, 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.
[Typical contact hours: lecture 52.5, laboratory 105]
Prerequisite Skills:
Before entering the course, the student should be able to:
1.
solve problems involving gas phase equilibria;
2.
determine the extent of acid-base, precipitation and complex equilibria;
3.
interpret reactions in terms of Arrhenus, Bronsted-Lowry and Lewis acid-base theory;
4.
predict whether oxidation-reduction reactions will occur and set up voltaic and electrolytic cells;
5.
describe factors that affect the rate of chemical reactions and match mechanism with reaction
rates;
6.
describe current models for the bonding of coordination compounds;
7.
perform problems involving complex ion equilibria;
8.
describe changes that occur in the nucleus of atoms;
9.
recognize organic compounds and simple isomers;
10.
analyze properties of family groups of the periodic table in terms of chemical principles;
11.
perform titrimetric experiments;
12.
measure pH with the use of pH meter or indicators;
13.
perform quantitative laboratory experiments in an accurate and precise manner;
14.
perform qualitative analysis of anions and cations in the laboratory;
15.
collect and analyze scientific data, using statistical and graphical methods;
16.
use a visible spectrophotometer;
17.
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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2.
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name compounds of the common organic functional groups using the IUPAC system of
nomenclature;
use a mechanistic approach to make reasonable predictions of major products formed in
reactions involving hydrocarbons, alkyl halides, alcohols and ethers;
explain physical and chemical properties of groups studied based on structural analysis;
use spectroscopic data from infrared spectroscopy, 1H nuclear magnetic spectroscopy to
elucidate structures for organic compounds;
identify structural isomers, stereoisomers and conformers and determine relationships between
pairs of structures;
predict and draw the possible conformations of acyclic and cyclic organic compounds and
analyze these conformation for relative stability;
identify stereocenters and chiral molecules and determine stereochemical relationships between
pairs of compounds;
Chabot College
Course Outline for Chemistry 12A, page 2
Fall 2006
8.
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use resonance theory and/or molecular theory to interpret reactivity of organic compounds;
suggest plausible single step and multi-step syntheses of hydrocarbons, alcohols, alkyl halides
and ethers;
analyze and explain nucleophilic substitutions reactions via SN1 and SN2 mechanisms, including
the influence of changes in structure of substrate and solvent;
analyze and explain elimination reactions via E1 and E2 mechanisms, including the influence of
changes in structure of substrate and solvent;
develop qualitative and quantitative problem solving skills;
perform basic laboratory techniques in organic laboratory: crystallization, simple and fractional
distillation, melting and boiling point determinations, extractions, chromatography, and
spectroscopy analysis;
explain the theory behind the techniques of crystallization, melting point determination, extraction,
distillation, boiling point determination and chromatographic separations;
synthesize, separate and analyze organic compounds using microscale and semi-microscale
methods;
effectively communicate observations and subsequent conclusions by means of keeping a bound
laboratory notebook and written laboratory reports;
utilize library and internet resources for information and in support of laboratory reports;
follow safe practices in handling and disposing of organic chemicals.
Course Content (Lecture):
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2.
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Review of General Chemistry Concepts:
a. Atomic structure and electron configurations
b. Bonding, hybrid orbitals and molecular shapes
c. Molecular structure and relationship to physical properties (boiling point, solubility, etc).
d. Acid/base theories
e. Determination of empirical and molecular formulas from quantitative analysis
Overview of Organic Chemistry:
a. Structure of major functional groups including hydrocarbons, alkyl halides, alcohols, ethers,
carbonyl compounds, amines and amides
b. Nomenclature of above functional groups
Alkanes:
a. Structure and physical properties
b. Sources of alkanes and industrial preparations
c. Laboratory preparations of alkanes
d. Reactions of alkanes including free radical halogenation
e. Detailed analysis of use of kinetics and mechanisms
f. Conformational analysis of open chain alkanes
g. Structure of cycloalkanes, including stability and conformational analysis
h. Stereochemistry of cycloalkanes
i. Preparation and reactions of cycloalkanes
Stereochemistry:
a. Polarimetry and optical activity
b. Chiral carbons and chiral substances
c. Enantiomers, diastereomers and racemic modifications
d. Specification of configuration, R/S
e. Synthesis and optical purity
f. Stereospecific reactions
g. Stereoselectivity vs. stereospecificity
Alkyl Halides:
a. Structure and physical properties
b. Laboratory preparations of alkyl halides
Chabot College
Course Outline for Chemistry 12A, page 3
Fall 2006
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c. Reactions of alkyl halides
d. Detailed analysis of nucleophilic substitution reactions (SN1 and SN2 mechanisms)
e. Solvent effects and secondary bonding
f. Carbocations and rearrangements
Alcohols:
a. Structure and physical properties
b. Industrial sources
c. Laboratory preparations of alcohols
d. Reactions of alcohols
e. Multi-step synthesis of alcohol
Ethers:
a. Structure and physical properties
b. Laboratory preparation of ethers
c. Reactions of ethers
Spectroscopy:
a. Introduction to Mass Spectroscopy and use in determining molar mass and molecular
formulas
b. Infrared Spectroscopy and use in elucidating basic molecular structures
c. 1H Nuclear Magnetic Resonance and use in elucidating molecular structures
Alkenes:
a. Structure and properties
b. Geometric Isomerism including specification of E/Z configurations
c. Laboratory preparations of alkenes
d. Detailed analysis of elimination reactions (E1 and E2 mechanisms)
e. Stereochemistry of E2 reactions, syn- and anti-elimination
f. Competition between elimination and substitution
g. Reactions of alkenes
h. Detailed analysis of addition reactions (electrophilic and free radical)
i. Stereochemistry of addition reactions, syn- and anti-addition
j. Free radical addition and substitution in alkenes including allylic rearrangements
Alkynes:
a. Structure and properties
b. Laboratory preparation of alkynes
c. Reactions of alkynes (including introduction of tautomerism via hydration)
d. Acidity of alkynes
Course Content (Laboratory):
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2.
Techniques:
a. Boiling Point and Melting Point Determination
b. Extraction
c. Simple and Fractional Distillation
d. Polarimetry
e. Crystallization
f. Thin layer and column chromatography
g. Refractometry
h. Vacuum Sublimation
i. Infrared Spectroscopy
j. Synthesis of simple compounds
Safety:
a.
Correct handling of organic compounds
b. Use of literature (Reference books such as Merck Index, etc and MSDS sheets) and internet
resources to determine possible hazards and safe handling procedures
Chabot College
Course Outline for Chemistry 12A, page 4
Fall 2006
Methods of Presentation:
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Lecture and class discussions
Models, computerized molecular modeling, videos, and transparencies
Demonstrations and computer simulations
Problem solving exercises
Hands-on laboratory work with direct access to all instrumentation
Assignments and Methods of Evaluating Student Progress:
1. Typical Assignments
a. Read the chapter on alkanes in your text
1) complete all the designated end of the chapter problems
2) using models, complete the assignment on conformations
b. Synthesize acetylsalicylic acid, otherwise known as aspirin
1) purify your product by crystallization using water as solvent
2) calculate the percent yield for your reaction
3) obtain the melting point of your product and compare it to the
literature value. Cite your literature reference.
2. Methods of Evaluating Student Progress
a. Quizzes
b. Midterm examinations
c. Homework assignments
d. Written lab reports
e. Written lab notebooks
f. Final exam
Textbook(s) (Typical):
Organic Chemistry, Wade, Prentice Hall Publishers, 2005
Introduction to Organic Laboratory Techniques, a Microscale Approach, Pavia, Lampman, Kriz, and
Engel, Saunders College Publishers, 1999
Special Student Materials:
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Molecular model kit
Scientific calculator
Safety goggles approved for chemistry laboratory
Laboratory notebook with sewn-in pages
DG/al
Revised 10/18/05