Updated: 5/26/99
Required of all sophomores majoring in chemistry. A study of the aliphatic hydrocarbons, their preparations and reactions, with emphasis on reaction mechanisms and transforrnations. Lecture: three hours.
Prerequisites: CHEM 152 and CHEM 162; Chemistry majors must have a grade of C or higher. Three Credit Hours
Text: McMurry, "Organic Chemistry," 3rd Edition
Instructor: Dr. J.R. Blanton (additional informatiion may be found here), 103 Byrd Hall
After completing this course, the student will gain an understanding of the following reaction processes: electrophilic additions, free radical additions, nucleophilic substitutions (SN1 and SN2), free radical substitutions, and eliminations (E1 and E2). In order to more fully grasp these concepts the student will also learn about the aspects of carbon stereochemistry and how molecules are identified via modern spectroscopic techniques.
In attaining the goals set for this course, the student will learn how to predict the products of reactions, propose mechanisms for reactions, develop synthesis schemes for specific target molecules, name and draw chemical compounds, and be able to use modern instrumentation techniques to analyze basic organic molecules.
The tests and final exam for this course will be keyed to the skills the student is to master. A summary database will be maintained to chart the progress of the class in each area to observe how well the goals of the course are met relative to the standards for the course. Should a problem be detected, the course materials (notes, examples, text, etc.) will be reviewed for possible action
I. Chemical Bonds and General Chemistry
A. Organic Chemistry---Historical Overview
B. Structural Theory and Isomerism
C. Chemical Bonds
i. Ionic
ii. Covalent
D. Formal Charges and Resonance
E. M.O. Theory
i. sp Hybridization
ii. sp2 Hybridization
iii. sp3 Hybridization
F. Polar and Nonpolar Molecules
G. Drawing Chemical Structures
H. Acid-Base Theory
i. Bronsted-Lowry
ii. Lewis
iii. Physical Properties and Molecular Structure
iv. Illustrating Reactions
v. Relative Strength
II. Representative Carbon Compounds
A. Alkanes
B. Alkenes
C. Alkynes
D. Functional Groups
III. Alkanes and Cycloalkanes
A. Nomenclature
B. Physical Properties
C. Conformational Analysis
i. Linear Alkanes
ii. Cycloalkanes
D. Reactions of Alkanes
E. Synthesis of Alkanes
IV. Alkenes and Alkynes. Properties and Synthesis
A. Nomenclature
B. Physical Properties
C. Uses of Hydrogenation
D. Stabilities
E. Synthesis of Alkenes and Alkynes
F. Properties of Terminal Alkynes
G. Introduction to Multi-step Syntheses
V. Reactions of Alkenes and Alkynes
A. Electrophilic Additions with Alkenes
i. Hydrogen Halides
ii. Water
iii. Halogens
iv. Stereochemistry
v. Halohydrins
vi. Epoxidation
B. Oxidations
C. Reactions with Carbocations
D. Electrophilic Additions with Alkynes
i. Hydrogen Halides
ii. Water
iii. Halogens
iv. Stereochemistry
v. Halohydrins
vi. Epoxidation
E. Planning Organic Syntheses
VI. Free Radical Reactions
A. Homolytic Bond Dissociations
B. Geometry of Free Radical
C. Reactions
i. Substitutions
ii. Additions
VII. Stereochemistry
A. Isomers
i. Constitutional
ii. Stereoisomers
B. Enantiomers and Chirality
C. Nomenclature: Cahn, Ingold, and Prelog Rules
D. Optical Activity
E. Other Stereoisomers
i. Diastereomers
ii. Meso Compounds
F. Fischer Projections
G. Relating Configuration
H. Resolution
VIII. Polar Reactions
A. Nucleophilic Substitution Reactions
i. Unimolecular
ii. Bimolecular
B. Nucleophiles
C. Kinetics
D. Mechanisms
E. Transition States and Energy Diagrams
F. Stereochemistry
G. Alkyl Halides in Synthesis
H. Elimination Reactions
i. Unimolecular
ii. Bimolecular
I. Comparison of Elimination vs. Substitution
IX. Conjugation and Diene Chemistry
A. Resonance
B. Conjugation and Stability
i. Molecules
ii. Ions
C. Thermodynamic vs. Kinetic Control
D. Pericyclic Reactions
X. Spectroscopy
A. Infrared Spectroscopy
B. Nuclear Magnetic Resonance Spectroscopy
i. Proton
ii. Carbon
C. Interpretation and Structure Determination
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