CHM 263 - Organic Chemistry I

Credits: 5
Lecture Hours: 3
Lab Hours: 4
Practicum Hours: 0
Work Experience: 0
Course Type: Core

1. Evaluate information from General Chemistry I and II
   1. Recall atomic structure
   2. Illustrate electronegativity trends
   3. Distinguish between ionic and covalent bonding
   4. Relate thermodynamics to organic reactions
   5. Apply kinetics to organic reactions

2. Assess Acid/Base Chemistry as it applies to organic chemistry
   1. Identify an acidic proton
   2. Utilize molecular structure as it relates to acidity
   3. Apply acid strength to reaction outcomes
   4. Compare relative acid strength to base strength
   5. Identify Lewis Acids and Lewis Bases

3. Evaluate 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. Distinguish between resonance structures and isomers
   5. Identify when resonance is possible in an organic molecule
   6. Draw appropriate resonance structures using standard electron movement designations
   7. Identify more or less important resonance structures

4. Appraise the relationship between systemic names and structures of organic molecules
   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

5. Assess the stereochemistry and molecular three-dimensionality of organic molecules
   1. Apply the correct stereochemistry for an asymmetric carbon using the R/S convention
   2. Apply the correct stereochemistry for an alkene using the E/Z convention
   3. Apply the correct stereochemistry for molecules that are identifiable as cis/trans
   4. Name organic molecules with the proper stereochemical designations
   5. Draw and identify enantiomers and diastereomers
   6. Understand the stereochemistry rules of Fischer projections and the meaning of those structures
   7. Relate chirality to optical activity
   8. Solve specific rotation and enantiomeric excess problems

6. Evaluate the correlation between structure and reactivity of organic molecules
   1. Calculate heats of reaction from bond dissociation energies
   2. Distinguish between homolytic and heterolytic bond cleavage
   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. Identify a nucleophile and an electrophile
   7. Interpret reaction energy diagrams
   8. Construct reaction mechanisms with the proper curved arrows
   9. Explain reaction intermediate stability 

7. Interpret infrared (IR) spectra
   1. Relate features in organic molecules which give rise to the absorption of infrared radiation
   2. Relate the position of the infrared absorption to the molecular feature responsible for it

8. Compare and contrast the properties of alkenes and alkynes
   1. Describe the bonding in alkenes and alkynes
   2. Illustrate various preparations of alkenes and alkynes
   3. Predict physical properties of alkenes and alkynes
   4. Predict products of various addition reactions of alkenes and alkynes including stereochemistry if necessary
   5. Write mechanisms for alkene and alkyne reactions
   6. Relate the structure of alkenes and alkynes to oxidation products
   7. Outline syntheses for various molecules beginning with alkenes or alkynes

9. Compare and contrast the properties of the alkyl halides
   1. Distinguish between various classifications of alkyl halides
   2. Predict various physical properties of alkyl halides
   3. Compare the nature of substitution and elimination reactions
   4. Write the mechanism for an S_N2 substitution
   5. Write the mechanism for an S_N1 substitution
   6. Compare various aspects of the S_N1 and S_N2 reactions
   7. Write a mechanism for an E1 elimination
   8. Write a mechanism for an 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

10. Interpret 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. Predict the product mixtures expected from bromination or chlori­nation of alkanes
    8. Describe the functions of free radical initiators

11. Compare and contrast the properties of alcohols
    1. Distinguish between various classifications of alcohols
    2. Predict various physical properties of alcohols
    3. Illustrate the acid-base properties of alcohols
    4. Use various methods to demonstrate alcohol preparations
    5. Predict products of various alcohol reactions including stereochemistry if necessary
    6. Write mechanisms for various alcohol reactions
    7. Identify redox in organic reactions
    8. Outline syntheses for more complex molecules from specific start­ing materials

12. Compare and contrast the properties of ethers
    1. Predict various physical properties of ethers
    2. Demonstrate the preparation of ethers using a variety of methods
    3. Predict products of ether substitution reactions including stereochemistry if necessary
    4. Write mechanisms for ether substitution reactions

13. Perform in various organic laboratory techniques proficiently
    1. Use capillary melting points to determine the purity of a solid sample
    2. Perform simple or fractional distillation as required
    3. Recrystallize impure solids to improve purity
    4. Perform simple chromatographic separations
    5. Use a separatory funnel to do liquid-liquid extractions
    6. Follow detailed experimental procedures
    7. Work safely and professionally in the organic chemistry laboratory

 
Competencies Revised Date: AY2025