CHM 273 - Organic Chemistry II

1. Relate topics from CHM 263 to appropriate material in CHM 273
2. Investigate the properties of alkenes and alkynes
   1. Describe the bonding in alkenes and alkynes
   2. Review the nomenclature of alkenes and alkynes
   3. Illustrate various preparations of alkenes and alkynes
   4. Predict physical properties of alkenes and alkynes
   5. Review spectral properties of alkenes and alkynes
   6. Predict products of various addition reactions of alkenes and alkynes including stereochemistry if necessary
   7. Write mechanisms for alkene and alkyne reactions
   8. Relate the structure of alkenes and alkynes to oxidation products
   9. Compare 1,2 addition to 1,4 addition for conjugated dienes
   10. Outline syntheses for various molecules beginning with alkenes or alkynes
3. Examine the properties of aromatic hydrocarbons
   1. Assign systematic names to benzene derivatives
   2. Describe the physical properties of aromatic hydrocarbons
   3. Review the spectral properties of aromatic hydrocarbons
   4. Classify compounds as aromatic, antiaromatic, or non-aromatic
   5. Write a mechanism for electrophilic aromatic substitution
   6. Predict products of the reactions of benzene with various other reagents
   7. Explain the differences between ortho-para and meta directors using resonance theory
   8. Predict the most likely products of electrophilic aromatic substitu­tion on substituted benzene rings
   9. Determine the effect of the aromatic ring on alkyl substituents
   10. Use resonance to explain the unusual properties of phenol
   11. Illustrate the chemical reactions of benzene diazonium salts
   12. Distinguish between electrophilic and nucleophilic aromatic substi­tution mechanisms
   13. Outline syntheses of compounds beginning with various aromatic hydrocarbons
4. Compare the properties of aldehydes and ketones.
   1. Review the nomenclature of aldehydes and ketones
   2. Illustrate various methods of preparing aldehydes and ketones
   3. Compare the physical properties of aldehydes and ketones
   4. Compare the spectral properties of aldehydes and ketones
   5. Predict products of addition reactions of aldehydes and ketones
   6. Predict products of addition-elimination reactions of aldehydes and ketones
   7. Predict products of redox reactions involving aldehydes and ketones
   8. Use resonance to explain the reactivity of alpha hydrogen atoms in aldehydes and ketones
   9. Predict products of various reactions involving the alpha carbon
   10. Predict products of 1,4 addition reactions of alpha-beta-unsaturated aldehydes and ketones
   11. Write mechanisms for various aldehyde and ketone reactions
   12. Outline syntheses of compounds beginning with aldehydes or ketones
5. Investigate the properties of carboxylic acids
   1. Review the nomenclature of carboxylic acids
   2. Predict various physical properties of carboxylic acids
   3. Review the spectral properties of carboxylic acids
   4. Illustrate various methods for preparing carboxylic acids
   5. Analyze the relationship between acid strength and acid structure
   6. Predict products of reactions of carboxylic acids with various bases
   7. Write a complete mechanism for the esterification of a carboxylic acid
   8. Predict the products of reduction reactions of carboxylic acids
   9. Investigate the special properties of dicarboxylic acids
   10. Predict products of 1,4 addition involving alpha-beta-unsaturated carboxylic acids
   11. Outline syntheses for other molecules beginning with carboxylic acids
6. Examine the properties of amines
   1. Recognize the classifications of amines
   2. Review the nomenclature of amines
   3. Predict various physical properties of amines
   4. Review the spectral properties of amines
   5. Illustrate various preparations of amines
   6. Relate the basicity of amines to various structural features of the amines
   7. Predict products of reactions of amines with a variety of acids
   8. Predict products of various substitution reactions involving amines
   9. Compare the products of various amine classes reacting with nitrous acid
   10. Use Hofmann elimination data to determine the structure of an amine
   11. Outline syntheses for compounds from amines
7. Compare the properties of various carboxylic acid derivatives
   1. Compare the relative reactivities of carboxylic acid derivatives
   2. Compare the spectral properties of carboxylic acid derivatives
   3. Extend the nomenclature system to the various carboxylic acid derivatives
   4. Illustrate the preparation of acid chlorides
   5. Predict products of reactions of acid chlorides
   6. Illustrate the preparation of acid anhydrides
   7. Predict products of reactions of acid anhydrides
   8. Illustrate the preparation of esters
   9. Predict products of the reactions of esters
   10. Illustrate the preparation of amides
   11. Predict products of the reactions of the amides
   12. Illustrate the preparation of nitriles
   13. Predict products of the reactions of nitriles
   14. Write mechanisms for various examples of nucleophilic acyl substi­tution
   15. Outline syntheses of compounds beginning with various carboxylic acid derivatives
8. Examine various reactions of enolate anions
   1. Review the acidity of various types of alpha hydrogen atoms
   2. Predict products of various alkylation reactions at the alpha carbon
   3. Relate the aldol condensation to similar reactions
   4. Predict products of ester condensations
   5. Predict products of nucleophilic 1,4 additions to alpha-beta-unsatu­rated carbonyl compounds
   6. Write mechanisms for various reactions involving enolate anions
   7. Outline syntheses for compounds using various condensation reac­tions
9. Perform various laboratory exercises
   1. Review various laboratory techniques used in CHEM161
   2. Synthesize various organic compounds using methods discussed in CHEM162
   3. Relate laboratory procedures to class material