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SYLLABUS

Catalog Description

Part one of the study of carbon compound chemsitry covering: atomic and molecular orbitals; stereochemistry; nomenclature, structure, reaction mechanisms, and laboratory synthesis of akanes, alkenes, and alcohols. Gas chromatography, along with infrared, mass, and nuclear magnetic resonance spectroscopies are taught and used for compound identification. For pre-professional majors. Prerequisite: CHEM 112 or equivalent. Semester Offered-On Demand.

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

1. 3D visualization: hybridization, orbital overlap, resonance, and molecular structure.
2. nomenclature, properties, and reactions of alkanes.
3. substitution and elimination reaction mechanisms with symmetry considerations.
4. nomenclature, properties, and reactions of alkenes.
5. nomenclature, properties, and reactions of alcohols.
6. laboratory synthesis: techniques, gas chromatography; infra red, mass, and nuclear magnetic resonance spectroscopies.

Specific Objectives: At the end of this course the student will be able to:
 

• 1.1 Draw resonance structures and use them to predict stabilities of radicals and ions.
• 1.2 Identify nucleophiles and electrophiles, and predict Lewis acid-base reactions.
• 1.3 Predict hybridization and geometry of atoms in molecules.
• 1.4 Describe sigma and pi bonding in terms of orbital overlap.
• 1.5 Identify structural isomers and stereoisomers.
• 1.6 Predict boiling and melting points based on structure.
• 2.1 Name and draw alkanes.
• 2.2 Compare the energies of alkane conformations and predict the most stable conformations.
• 2.3 Explain the mechanism and energetics of the free-radical halogenation of alkanes.
• 2.4 Predict the products of halogenation of an alkane.
• 2.5 Explain how to use isotope effects to determine whether a C-H bond is being broken in the rate-determining step of a reaction.
• 3.1 Predict the products of SN1, SN2, E1, and E2 reactions including stereochemistry.
• 3.2 Classify molecules as chiral or achiral, and identify mirror planes of symmetry.
• 3.3 Identify enantiomers, diastereomers, and meso compounds.
• 3.4 Draw Fischer projections of chiral carbon atoms.
• 3.5 Predict the stereochemistry of products of reactions such as substitutions and eliminations on optically active compounds.
• 4.1 Predict relative stabilities of alkenes and cycloalkenes based on structure and stereochemistry.
• 4.2 Propose logical mechanisms for dehydrohalogenation, dehalogenation, and dehydration reactions.
• 4.3 Predict the products of additions, oxidations, reductions, and cleavages of alkenes, including regiochemistry and sterochemistry.
• 4.4 Use alkenes in devising single step and multistep synthesis.
• 5.1 Show how to convert alkenes, alkyl halides, and carbonyl compounds to alcohols.
• 5.2 Predict alcohol products of hydration, hydroboration, and hydroxylation of alkenes.
• 5.3 Use retrosynthetic analysis to propose effective syntheses of compounds using alcohols.
• 6.1 Synthesize and ivestigate reactions of alkyl halides, alkenes, and alcohols in the laboratory.
• 6.2 Apply chemical and physical tests to identify organic compounds.
• 6.3 Identify key components and principles of operation of a gas chromatograph.
• 6.4 Use gas chromatography to separate and identify components of a mixture.
• 6.5 Describe how an infrared spectrophotometer works.
• 6.6 Given an IR spectrum, idententify functional groups.
• 6.7 Describe how a mass spectrometer works.
• 6.8 Use the fragmentation pattern of a mass spectrum to determine structure.
• 6.9 Describe how a nuclear magnetic resonanance spectrometer works.
• 6.10 Combine the chemical shifts, intergrals, and spin-spin splitting patterns in the NMR spectrum with information from IR and MS to determine the structures of organic compounds.