SYLLABUS

CHEM 252 Organic Chemistry II (3+3P) 4 credits

Catalog Description

Part two of the study of carbon compound chemistry covering: structure and reaction mechanisms of carboxyl, amine, conjugated, and polyfunctional systems; ultraviolet spectroscopy; biochemistry; and synthetic polymers. Prerequisite: CHEM 251 or equivalent. Semester Offered-On Demand.

General Objectives: Upon completion of the course, the student should have a working knowledge of the following:
 

1. nomenclature, properties, and reactions of ethers and epoxides.
2. nomenclature, properties, and reactions of alkynes.
3. electronic structure, ultraviolet spectroscopy, and reactions of conjugated systems.
4. electronic structure, spectroscopies, and nomenclature of aromatic compounds.
5. reactions of aromatic compounds.
6. nomenclature, properties, and reactions of ketones and aldehydes.
7. nomenclature, properties, and reactions of amines.
8. nomenclature, properties, and reactions of carboxylic acids and derivatives.
9. additions and condensations of enols and enolate ions.
10. nomenclature, properties, and reactions of carbohydrates, and nucleic acids.
11. nomenclature, properties, and reactions of amino acids, peptides, and proteins.
12. nomenclature, properties, and reactions of lipids.
13. nomenclature, properties, and reactions of synthetic polymers.

Specific Objectives. Upon completion of this course the student should be able to:
 

• 1.1 Propose Williamson ether synthesis of ethers.
• 1.2 Show the mechanism of epoxidation and acid catalyzed ring opening and cyclization related to the biosynthesis of steroids.
• 2.1 Show how to synthesize alkynes from acetlyides and alkyl halides.
• 3.1 Construct molecular orbitals and electronic configurations of simple conjugated systems.
• 3.2 Predict the products of Diels-Alder reactions.
• 3.3 Use HOMO-LUMO interactions to predict thermal or photochemical cycloadditions.
• 3.4 Predict UV absorption maxima of conjugated systems.
• 4.1 Construct and interpret molecular orbitals and electronic configurations of aromatics.
• 4.2 Use the polygon rule on conjugated cyclic systems to determine aromaticity.
• 4.2 Use IR, NMR, UV, and MS to determine the structures of aromatic compounds.
• 5.1 Predict products and give mechanisms for electrophillic aromatic substitutions.
• 5.2 Design syntheses that use the influences of substituents to generate the correct isomers of multisubstituted aromatic compounds.
• 5.3 Explain how Friedel-Crafts Acylation overcomes two of the three limitations of Friedel- Crafts Alkylation
• 6.1 Show how to synthesise ketones and aldehydes from oxidation of alcohols, ozonolysis, Friedel-Crafts acylations, organolithiums, and acid chlorides.
• 6.2 Show mechanisms of nucleophillic additions and condensation reactions.
• 6.3 Interpret the IR, NMR, UV, and MS of ketones and aldehydes.
• 6.4 Predict the products of McLafferty rearrangement in the Mass Spectrometer
• 6.5 Predict the approximate values of 8max for n 6 B* and B 6 B* transitions.
• 7.1 Show how to synthesize amines by reductive amination and acylation-reduction.
• 7.2 Predict basicity of amines.
• 7.3 Use amines in synthesis.
• 7.4 Interpret the IR, NMR, UV, and MS of amines.
• 8.1 Use carboxylic acids and derivatives in fisher esterification and hydrolysis reactions.
• 8.2 Show how to interconvert acid derivatives by nucleophillic Acyl Substitution.
• 8.2 Interpret the IR, NMR, UV, and MS of carboxylic acids.
• 9.1 Predict the products and give mechanisms of Aldol, Wittig, and Claisen reactions.
• 10.1 Identify essential features of carbohydrates and nucleic acids.
• 10.2 Recognize the anomers and epimers of glucose.
• 10.3 Name monosaccharides and disaccharides, and draw their structures from their names.
• 10.4 Predict reaction products involving carbohydrates.
• 10.5 Recognize the structures of DNA and RNA, and draw the structures of a ribonucleotide and deoxyribonucleotide.
• 11.1 Name amino acids and peptides, and draw the structures from their names
• 11.2 Explain which amino acids are acidic, basic, or neutral.
• 11.3 Show how an amino acid is synthesized.
• 11.4 Show how classical and solid-phase peptide synthesis would be used to make a given peptide.
• 11.5 Discuss and identify the four levels of protein structure.
• 12.1 Classify lipids.
• 12.2 Predict physical properties of fats and oils.
• 12.3 Identify isoprene units in terpenes.
• 12.4 Explain how soaps and detergents work.
• 13.1 Given the structure of a synthetic polymer, determine whether it is an addition or condensation polymer, and determine the structure of the monomer(s).
• 13.2 Predict the general characteristics of a given polymer.