CHM 273 - Organic Chemistry II

1. Incorporate knowledge of Organic Chemistry I
   1. Recall nomenclature rules of Organic Chemistry I
   2. Illustrate reactivity patterns discussed in Organic Chemistry I
2. Evaluate nuclear magnetic resonance (NMR) spectra
   1. Examine nuclear magnetic resonance theory to explain why different protons and carbon atoms in a molecule have different chemical shifts
   2. Interpret the relative numbers of protons in NMR signals from an integration curve
   3. Relate the splitting in an NMR signal to the number of neighboring protons
   4. Contrast proton NMR to carbon-13 NMR
   5. Identify the structure of an unknown organic molecule from its formula and spectral data
3. 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
4. Evaluate the properties of carboxylic acids
   1. Interpret various physical properties of carboxylic acids
   2. Show the special properties of dicarboxylic acids
   3. Illustrate various methods for preparing carboxylic acids
   4. Analyze the relationship between acid strength and acid structure
   5. Predict products of reactions of carboxylic acids with various bases
   6. Write a complete mechanism for the esterification of a carboxylic acid
   7. Solve for the products of reduction reactions of carboxylic acids
   8. List products of 1,4 addition involving alpha-beta-unsaturated carboxylic acids
   9. Outline syntheses for other molecules beginning with carboxylic acids
5. Compare and contrast the properties of various carboxylic acid derivatives
   1. Compare the relative reactivities of carboxylic acid derivatives
   2. Illustrate the preparation of acid chlorides, acid anhydrides, esters, amides and nitriles
   3. Show the products of reactions of acid chlorides, acid anhydrides, esters, amides and nitriles 
   4. Illustrate mechanisms for various examples of nucleophilic acyl substi­tution
   5. Plan syntheses of compounds beginning with various carboxylic acid derivatives
6. Compare and contrast the properties of aldehydes and ketones.
   1. Illustrate various methods of preparing aldehydes and ketones
   2. Compare the physical properties of aldehydes and ketones
   3. Predict products of addition reactions of aldehydes and ketones
   4. Predict products of addition-elimination reactions of aldehydes and ketones
   5. Predict products of redox reactions involving aldehydes and ketones
   6. Use resonance to explain the reactivity of alpha hydrogen atoms in aldehydes and ketones
   7. Predict products of various reactions involving the alpha carbon
   8. Predict products of 1,4 addition reactions of alpha-beta-unsaturated aldehydes and ketones
   9. Write mechanisms for various aldehyde and ketone reactions
   10. Outline syntheses of compounds beginning with aldehydes or ketones
7. Evaluate various reactions of enolate anions
   1. Examine the acidity of various types of alpha hydrogen atoms
   2. Show products of various alkylation reactions at the alpha carbon
   3. Compare the aldol condensation to similar reactions
   4. Show the products of ester condensations
   5. Show the products of nucleophilic 1,4 additions to alpha-beta-unsatu­rated carbonyl compounds
   6. Illustrate mechanisms for various reactions involving enolate anions
   7. Outline syntheses for compounds using various condensation reac­tions
8. Evaluate the properties of amines
   1. Classify different categories of amines
   2. Examine various physical properties of amines
   3. Illustrate various preparations of amines
   4. Compare the basicity of amines to various structural features of the amines
   5. Show the products of reactions of amines with a variety of acids
   6. Show the products of various substitution reactions involving amines
   7. Analyze Hofmann elimination data to determine the structure of an amine
   8. Outline syntheses for compounds from amines
9. Evaluate molecules with delocalized electrons
   1. Explain the stability of compounds with delocalized electrons
   2. Illustrate delocalization of electrons in conjugated double bond systems
   3. Illustrate the importance of resonance with delocalized electrons
   4. Examine Reactions of Dienes
   5. Explain kinetic versus thermodynamic control
   6. Develop an understanding of the Diels-Alder Reaction
   7. Explain the directing effects of the Diels-Alder Reaction
   8. Illustrate the stereochemistry of the Diels-Alder Reaction
10. Assess the properties of aromatic hydrocarbons
    1. Explain the physical properties of aromatic hydrocarbons
    2. Define compounds as aromatic, antiaromatic, or non-aromatic
    3. Illustrate a mechanism for electrophilic aromatic substitution
    4. Solve for the products of the reactions of benzene with various other reagents
    5. Explain the differences between ortho-para and meta directors using resonance theory
    6. Show the most likely products of electrophilic aromatic substitu­tion on substituted benzene rings
    7. Determine the effect of the aromatic ring on alkyl substituents
    8. Illustrate the chemical reactions of benzene diazonium salts
    9. Explain electrophilic and nucleophilic aromatic substi­tution mechanisms
    10. Outline syntheses of compounds beginning with various aromatic hydrocarbons
11. Perform various laboratory exercises
    1. Relate various laboratory techniques used in CHM263
    2. Apply knowledge to synthesize various organic compounds using methods discussed in CHM273
    3. Relate laboratory procedures to class material
    4. Work safely and professionally in the organic chemistry laboratory