CHM 263 - Organic Chemistry I

1. Evaluate information from general chemistry which is most applicable to organic chemistry
   1. Predict electronic structure of atoms
   2. Match the size of an atom to its position on the periodic table
   3. Select which of two elements has the higher electronegativity
   4. Distinguish between ionic and covalent bonding
   5. Write various types of formulas for organic molecules
   6. Define bond lengths
   7. Define bond angles
   8. Calculate heats of reaction from bond dissociation energies
   9. Distinguish between homolytic and heterolytic bond cleavage
   10. Review the nature of polar covalent bonds
   11. Recognize the principle attractive forces which are used by covalent molecules
   12. Extend acid-base chemistry to organic molecules
2. Investigate the basic structure of organic molecules
   1. Describe chemical bonding using molecular orbital theory
   2. Use valence-bond (hybridization) theory to explain chemical bond­ing
   3. Identify functional groups in organic molecules
   4. Illustrate delocalization of electrons in conjugated double bond systems
   5. Distinguish between resonance structures and isomers
   6. Recognize when resonance is possible in an organic molecule
   7. Draw appropriate resonance structures using standard electron movement designations
   8. Identify more or less important resonance structures
3. Relate the structure of an organic molecule to its systematic name
   1. Draw structures for the various isomers represented by a certain molecular formula
   2. Outline a system for naming organic compounds based upon their structures
   3. Apply the nomenclature system to a variety of organic molecules containing different functional groups
4. Investigate the chemistry of the simplest organic molecules, the alkanes
   1. Predict various physical properties of alkanes based on structure
   2. Illustrate complete combustion of an alkane with chemical equa­tions
   3. Predict products of halogen substitution reactions of alkanes
5. Generate appropriate pictures to model the three-dimensional structure of organic molecules
   1. Draw structures showing cis-trans (E-Z) isomerism in alkenes
   2. Recognize cis-trans isomerism in cycloalkanes
   3. Show conformations of open chain compounds using various pro­jections
   4. Identify the relative energies of molecular conformations
   5. Draw various conformations of cyclohexane derivatives
   6. Illustrate chirality using structures
   7. Relate chirality to the rotation of plane-polarized light
   8. Assign absolute configuration to a chiral carbon atom using the R-S system
   9. Extend the description of a chiral molecule to systems containing more than one chiral center
   10. Name organic molecules including the appropriate stereochemical designations
   11. Describe various methods of resolving racemic mixtures
6. Examine the properties of the alkyl halides
   1. Recognize various classifications of alkyl halides
   2. Predict various physical properties of alkyl halides
   3. Review the nomenclature of alkyl halides
   4. Compare the nature of substitution and elimination reactions
   5. Write the mechanism for an SN2 substitution
   6. Write the mechanism for an SN1 substitution
   7. Compare various aspects of the SN1 and SN2 reactions
   8. Write a mechanism for an E1 and E2 elimination
   9. Compare various aspects of the E1 and E2 reactions
   10. Identify the factors which favor substitution or elimination reac­tions
   11. Predict which reaction mechanism is most likely based upon the conditions
   12. Predict products of alkyl halide reactions with various nucleophile/bases
7. Investigate the mechanism of free radical reactions
   1. Use halogenation of alkanes as a model of a free radical reaction
   2. Write mechanistic steps for a free radical chain mechanism
   3. Explain why chlorine is more reactive than bromine in free radical halogenation
   4. Explain why chlorine is less selective than bromine in free radical halogenation
   5. Describe the stereochemical consequences of free radical halogen­ation at a chiral carbon atom
   6. Relate the rate of free radical halogenation to the strength of the carbon-hydrogen bond broken
   7. Illustrate the use of NBS as a selective halogenating agent
   8. Predict the product mixtures expected from bromination or chlori­nation of alkanes
   9. Describe the functions of free radical initiators
   10. Describe the function of free radical inhibitors
8. Examine the properties of alcohols
   1. Recognize various classifications of alcohols
   2. Extend the nomenclature of alcohols to include a wider variety of cases
   3. Predict various physical properties of alcohols
   4. Illustrate the acid-base properties of alcohols
   5. Use various methods to demonstrate alcohol preparations
   6. Predict products of various alcohol reactions including stereo-chemistry if necessary
   7. Write mechanisms for various alcohol reactions
   8. Recognize redox in organic reactions
   9. Outline syntheses for more complex molecules from specific start­ing materials
9. Investigate the properties of ethers
   1. Predict various physical properties of ethers
   2. Extend the nomenclature of ethers to include more complex struc­tures
   3. Demonstrate the preparation of ethers using a variety of methods
   4. Predict products of ether substitution reactions including stereo-chemistry if necessary
   5. Write mechanisms for ether substitution reactions
10. Interpret infrared (IR) and nuclear magnetic resonance (NMR) spectra
    1. Recognize features in organic molecules which give rise to the absorption of infrared radiation
    2. Correlate the position of the infrared absorption to the molecular feature responsible for it
    3. Use nuclear magnetic resonance theory to explain why different protons in a molecule have different chemical shifts
    4. Determine relative numbers of protons in NMR signals from an integration curve
    5. Relate the splitting in an NMR signal to the number of neighboring protons
    6. Identify the structure of an unknown organic molecule from its formula and spectral data
11. Demonstrate proficiency in various organic laboratory techniques
    1. Use capillary melting points to determine the purity of a solid sample
    2. Perform simple or fractional distillation as required to separate the volatile components of a mixture
    3. Recrystallize impure solids to improve purity
    4. Perform simple chromatographic separations
    5. Use a separatory funnel to do liquid-liquid extractions
    6. Construct molecular models to visualize stereochemical relation­ships
    7. Construct molecular models to visualize stereochemical relation­ships
    8. Obtain an infrared spectrum of a liquid sample