COURSE DESCRIPTION

Introduces fundamental chemistry of carbon compounds, including structures, physical properties, synthesis, and typical reactions. Emphasizes reaction mechanisms. Lecture 3 hours per week.

GENERAL COURSE PURPOSE

A sequence of courses designed to introduce the student to the chemistry of carbon compounds. It covers some of the historical aspects of organic chemistry as well as the relationships with industrial synthesis. Biochemical as well as polymer chemistry is included. It covers the wide variety of synthesis methods and chemical group reactions.

ENTRY-LEVEL COMPETENCIES

Completion of CHM 241 - "Organic Chemistry I" or permission of the instructor.

COURSE OBJECTIVES

As a result of the learning experiences provided in this course, the student should be able to:

A. use the information from the UV/Vis, IR, ¹H-NMR, ¹³C-NMR, and mass spectra to deduce the structure of the organic compound

B. give detailed consideration to specific classes of organic compounds and their types of reactions (such as amines, aldehydes, ketones, ethers, phenols, arenes, carboxylic acids, and carboxylic acid derivatives)

C. give detailed consideration to specific classes of polyfunctional compounds and their types of reactions (such as b-unsaturated carbonyl compounds, polyenes, dicarbonyl compounds (including quinones), hydroxy acids, and amino acids)

D. give detailed consideration to specific classes of complex compounds and their types of reactions (such as saccharides, polysaccharides, amino acids, polypeptides, nucleic acids, polynucleotides, alkaloids, and vitamins)

E. complete challenging sequence synthesis of the specific classes of compounds included in B, C, and D above

F. give to IUPAC and common names of the classes of compounds given in B, C, and D above

G. use the orbital symmetry rules to predict the correct cycloaddition products

MAJOR TOPICS TO BE COVERED
 

A. Conjugated systems, allylic systems and the use of molecular orbitals and orbital symmetry to explain the Reactions of these systems (including the Diels-Alder reaction)

B.  Ultraviolet absorption spectroscopy

C. Nomenclature, structures, and physical properties of benzene and polynuclear systems. Aromatic, antiaromatic, and nonaromatic compounds. Heterocyclic aromatic systems. Electrophilic aromatic substitution reactions (including halogenation, nitration, sulfonation, Friedel-Crafts alkylation, and Friedel-Crafts acylation reactions) and the effect of subtituents on the aromatic ring

D. ¹H, and ¹³C nuclear magnetic resonance spectroscopy (including chemical shift, relative areas of the various signals, spin-spin splitting, and nonequivalence in stereoisomeric forms)

E. Nomenclature, structures, physical properties, methods of preparation, and reactions of the aldehydes and ketones (including reduction,cyanohydrin formation, imine formation, enamine formation, ketal and acetal formation, oxidation reactions and deoxygenation reactions)

F. Infrared spectroscopy and mass spectroscopy. Major group absorptions in the infrared. Elementary concepts of mass spectroscopy

G. Basic functional-group tests

H. Nomenclature, structures, physical properties, methods of preparation, and reactions of the amine compounds (including alkylation, acylation, elimination, oxidation, and diazotization)

I. Nomenclature, structures, physical properties, methods of preparation, and reactions of the carboxylic acids and the carboxylic acid derivatives (acid halides, anhydrides, esters, amides, and nitriles)

J. Addition and condensation reactions of the enols and enolate ions. These will include the Aldol condensation, Cannizzaro reaction, Wittig reaction, Claisen condensation, and the Michael reaction.

K. Classification structure, stereochemistry, chemical and physical properties of the saccharides, Fischer's work on the absolute configuration of the monosaccharides, Ruff degradation, Kiliani-Fischer synthesis, epimerization, oxidation to aldonic acids and aldaric acids, reduction to poly-ols, nomenclature of the monosaccharides, disaccharides, and polysaccharides, nucleic acids with their base pairings

L. Classification, structure, stereochemistry, chemical and physical properties of the amino acids. Synthesis and reactions of the amino acids. Nomenclature of the amino acids, peptides, and proteins. Determination of the sequence of amino acids by Edman degradation, and the use of C-terminal analysis. The levels of protein structure.

M. The classes of lipids: waxes, triglycerides, phospholipids, steroids, and terpenes. Saponification, difference between soaps and detergents

N. Industrial polymerization: addition and condensation polymers. Stereochemistry of polymers. Free radical, cationic, and anionic polymerization

O. Nomenclature, structure, chemical and physical properties of the lactones, lactams, oxiranes, furans, pyrans, aziridines, azetidines, pyrrolidines, piperidines, pyridines, pyrimidines, and purines