20806257Organic Chemistry 2 Lecture
Course Information
Description
Continuation of Organic Chemistry 1. Includes the theory and interpretation of NMR and UV-VIS spectrophotometry; the nomenclature, mechanisms, reactions and properties of the following classes of compounds alkadienes, aromatic, aldehydes, ketones, enols/enolates, carboxylic acids, carboxylic acid derivatives, amines, aryl halides, and phenols. Includes multiple-strip syntheses involving all organic classes of molecules. This course completes the lecture portion of 1-year long sequence of basic organic chemistry curriculum.
Total Credits
4
Course Competencies
  1. Summarize the names and formulas for simple aromatic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the correct names for substituted benzene compounds
    Draw the correct structures for substituted benzene compounds

  2. Determine physical properties of aromatic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Summarize the trends in solubility for aromatic compounds
    Summarize the trends in boiling point for aromatic compounds
    Summarize the trends in density for aromatic compounds

  3. Predict products of aromatic reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products, conditions for halogenation aromatic reactions
    Write the reactants, products, conditions for Friedel-Crafts alkylation aromatic reactions
    Write the reactants, products, conditions for Friedel-Crafts acylation aromatic reactions
    Write the reactants, products, conditions for alkenes aromatic reactions
    Write the reactants, products, conditions for nitration aromatic reactions
    Write the reactants, products, conditions for sulfonation aromatic reactions
    Identify the groups that are ortho-para directing
    Identify groups that are meta directing
    Identify groups that are activating
    Identify groups that are deactivating
    Relate the stability of benzene to heat of hydrogenation data

  4. Summarize the mechanisms for reactions of aromatic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Outline the mechanism for electrophilic aromatic substitution

  5. Identify spectral characteristics of aromatic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Identify characteristics of aromatic compounds in NMR
    Identify characteristics of aromatic compounds in IR

  6. Explain the bonding in aromatic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Compare resonance and molecular orbital interpretations of aromatic compounds
    Identify characteristics of aromatic compounds
    Identify characteristics of aromatic ions

  7. Summarize the methods to synthesize substituted aromatic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products and conditions for Sandmeyer reactions of aryl diazonium salts
    Write the reactants, products and conditions for KI reactions of aryl diazonium salts
    Write the reactants, products and conditions for HBF4 reactions of aryl diazonium salts
    Write the reactants, products and conditions for water reactions of aryl diazonium salts
    Write the reactants, products and conditions for hypophosphorous acid reactions of aryl diazonium salts
    Write the reactants, products and conditions for activated aromatic rings reactions of aryl diazonium salts
    Write the reactants, products and conditions for the nucleophilic reactions of aryl halides with ammonia
    Write the reactants, products and conditions for the nucleophilic reactions of aryl halides with hydroxide
    Write the reactants, products and conditions for the nucleophilic reactions of aryl halides with water
    Write the reactants, products and conditions for synthesis of benzyne reactions
    Write the reactants, products and conditions for benzyne reactions
    Write the reactants, products and conditions for ammonia reactions

  8. Predict products of reactions of substituted aromatic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products and conditions for given compound with strong base reactions of phenols
    Write the reactants, products and conditions for given compound with acids reactions of phenols
    Write the reactants, products and conditions for given compound with anhydrides reactions of phenols
    Write the reactants, products and conditions for given compound with acyl halides reactions of phenols
    Write the reactants, products and conditions for reactions of phenols
    Write the reactants, products and conditions for oxidation reactions of phenols
    Write the reactants, products and conditions for oxidation of alkyl side chains reactions
    Write the reactants, products and conditions for halogenation at benzylic positions reactions
    Write the reactants, products and conditions for nitrous acid and aminobenzenes reactions
    Write the reactants, products and conditions for reduction of aromatic nitro groups reactions

  9. Summarize the mechanisms for reactions of substituted aromatic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Indicate the mechanism for the nucleophilic substitution reaction of aryl halides

  10. Compare acid-base properties of phenols with other organic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Compare the acidity of phenols with water
    Compare the acidity of phenols with other organic compounds

  11. Summarize the names and formulas for aldhydes and ketones
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the correct names for aldehydes
    Write the correct names for ketones
    Draw the correct structure for aldehydes
    Draw the correct structure for ketones

  12. Determine physical properties of aldehydes and ketones
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Summarize the trends in solubility for aldehydes
    Summarize the trends in solubility for ketones
    Summarize the trends in boiling point for aldehydes
    Summarize the trends in boiling point for ketones
    Summarize the trends in density for aldehydes
    Summarize the trends in density for ketones

  13. Predict products of aldehyde and ketone reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products, conditions for water reactions of aldehydes and ketones
    Write the reactants, products, conditions for alcohols reactions of aldehydes and ketones
    Write the reactants, products, conditions for HCN reactions of aldehydes and ketones
    Write the reactants, products, conditions for Grignard reagents reactions of aldehydes and ketones
    Write the reactants, products, conditions for addition-elimination reactions of aldehydes and ketones
    Write the reactants, products, conditions for oxidation reactions of aldehydes and ketones
    Write the reactants, products, conditions for reduction reactions of aldehydes and ketones

  14. Summarize the methods to synthesize aldehydes and ketones
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products, conditions for oxidation of alcohol reactions that produce aldehydes and ketones
    Write the reactants, products, conditions for alkynes + water reactions that produce aldehydes and ketones
    Write the reactants, products, conditions for the Friedel-Crafts acylation that produce aldehydes and ketones

  15. Explain the mechanisms for reaction of aldehydes and ketones
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Indicate mechanisms for keto-enol tautomerism
    Indicate mechanisms for alpha halogenation of aldehydes/ketones
    Indicate mechanisms for addition reactions of aldehydes/ketones
    Indicate mechanisms for addition-elimination reactions of aldehydes/ketones

  16. Compare acid-base properties of aldehydes and ketones
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Compare the acidity of alpha hydrogens to other acidic organic compounds

  17. Identify spectral characteristics of aldehydes and ketones
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Identify characteristics of aldehydes and ketones in NMR
    Identify characteristics of aldehydes and ketones in IR

  18. Summarize names and formulas for carboxylic acids
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the correct names for carboxylic acids
    Draw the correct structures of carboxylic acids

  19. Determine physical properties of carboxylic acids
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Summarize the trends in solubility for carboxylic acids
    Summarize the trends in boiling point for carboxylic acids
    Summarize the trends in density for carboxylic acids
    Relate hydrogen bonding to the solubility of carboxylic acids
    Relate hydrogen bonding to the boiling point of carboxylic acids

  20. Identify spectral characteristics of carboxylic acids
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Identify characteristics of carboxylic acids in NMR
    Identify characteristics of carboxylic acids in IR

  21. Explain the methods to synthesize carboxylic acids
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products and conditions for hydrolysis of nitriles and acyl derivatives reactions to synthesize carboxylic acids
    Write the reactants, products and conditions for oxidation of alcohols reactions to synthesize carboxylic acids
    Write the reactants, products and conditions for alkenes reactions to synthesize carboxylic acids
    Write the reactants, products and conditions for alkylbenzenes reactions to synthesize carboxylic acids
    Write the reactants, products and conditions for Grignard + CO2 reactions to synthesize carboxylic acids

  22. Predict products of carboxylic acid reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products, conditions for reactions with bases and carboxylic acids
    Write the reactants, products, conditions for reactions with alcohols and carboxylic acids
    Write the reactants, products, conditions for reactions with reducing agents and carboxylic acids
    Write the reactants, products, conditions for reactions with betadecarboxylation and carboxylic acids
    Write the reactants, products, conditions for reactions with anhydride formation and carboxylic acids

  23. Compare acid-base properties of carboxylic acids
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Compare the acidity of carboxylic acids with other acidic organic compounds

  24. Explain mechanisms for reactions of carboxylic acids
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Indicate the mechanism for an esterification reaction

  25. Summarize names and formulas for carboxylic acid derivatives
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the correct name for acyl halides
    Write the correct name for acid anhydrides
    Write the correct name for esters
    Write the correct names for amides
    Write the correct names for nitriles
    Write the correct name for lactams
    Write the correct name for imides
    Write the correct name for carbamates (urethanes), sulfonamides
    Write the correct name for sulfonamides
    Draw correct structure for acyl halides
    Draw correct structure for acid anhydrides
    Draw correct structure for esters
    Draw correct structure for nitriles
    Draw correct structure for lactams
    Draw correct structure for imides
    Draw correct structure for carbamates (urethanes)
    Draw correct structure for sulfonamides
    Draw correct structure amides

  26. Compare acid-base properties of carboxylic acid derivatives
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Compare the basicity of amides and nitriles to other basic organic compounds

  27. Explain the mechanisms for reaction of carboxylic acid derivatives
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Outline the addition-elimination mechanism for carboxylic acid derivatives

  28. Identify spectral characteristics of carboxylic acid derivatives
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Identify characteristics of carboxylic acid derivatives in NMR
    Identify characteristics of carboxylic acid derivatives in IR

  29. Explain the methods to synthesize carboxylic acid derivatives
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products and conditions for the following reactions for the synthesis of acid halides: acid + thionyl chloride or phosphorus trihalides
    Write the reactants, products and conditions for the following reaction for the synthesis of acid anhydrides: acyl halide + carboxylate salt
    Write the reactants, products and conditions for the following reaction for the synthesis of acid anhydrides: two acids
    Write the reactants, products and conditions for the following reaction for the synthesis of esters: alcohol + acid
    Write the reactants, products and conditions for the following reaction for the synthesis of esters: acid halide
    Write the reactants, products and conditions for the following reaction for the synthesis of esters: acid anhydride
    Write the reactants, products and conditions for the following reaction for the synthesis of esters: ester
    Write the reactants, products and conditions for the following reaction for the synthesis of nitriles: alkyl halide + cyanide
    Write the reactants, products and conditions for the following reaction for the synthesis of nitriles: Sandmeyer reaction
    Write the reactants, products and conditions for the following reaction for the synthesis of nitriles: dehydration of amides
    Write the reactants, products and conditions for the synthesis of polyesters and polyamides

  30. Predict products of carboxylic acid derivatives
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products, conditions for the reaction of acid halides with water
    Write the reactants, products, conditions for the reaction of acid halides with alcohols
    Write the reactants, products, conditions for the reaction of acid halides with ammonia or amines
    Write the reactants, products, conditions for the reaction of acid halides with aromatic compounds
    Write the reactants, products, conditions for the reaction of acid halides with Grignard reagents
    Write the reactants, products, conditions for the reaction of acid halides with reducing agents
    Write the reactants, products, conditions for the reaction of acid halides with halogens
    Write the reactants, products, conditions for the reaction of acid halides with carboxylate salts
    Write the reactants, products, conditions for the reaction of acid anhydrides with water
    Write the reactants, products, conditions for the reaction of acid anhydrides with alcohols
    Write the reactants, products, conditions for the reaction of acid anhydrides with ammonia or amines
    Write the reactants, products, conditions for the reaction of esters with water
    Write the reactants, products, conditions for the reaction of esters with alcohol
    Write the reactants, products, conditions for the reaction of esters with ammonia or amines
    Write the reactants, products, conditions for the reaction of esters with reducing agents
    Write the reactants, products, conditions for the reaction of esters with Grignard reagents
    Write the reactants, products, conditions for the reaction of amides with water
    Write the reactants, products, conditions for the reaction of amides with reducing agents
    Write the reactants, products, conditions for the reaction of nitriles with water
    Write the reactants, products, conditions for the reaction of nitriles with reducing agents

  31. Explain the mechanisms for conjugated dienes and enones
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Outline mechanisms for the following reactions: 1,2 and 1,4 addition to a conjugated diene
    Outline mechanisms for the following reactions: 1,4 additions to alpha, beta unsaturated carbonyl compounds
    Outline mechanisms for the following reactions: Diels-Alder

  32. Predict the reactants, conditions and products for diene and enone reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Predict the reactants, conditions and products for the following: Diels-Alder reaction
    Predict the reactants, conditions and products for the following: additions to alpha, beta unsaturated carbonyl compounds

  33. Explain the mechanisms for enolate and carbanion reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Indicate mechanisms for the following enolate and carbanion reactions reaction: alkylation
    Indicate mechanisms for the following enolate and carbanion reactions reaction: condensation

  34. Predict products of enolate and carbanion reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products, conditions for the malonic ester synthesis alkylation reaction
    Write the reactants, products, conditions for the acetoacetic ester synthesis alkylation reaction
    Write the reactants, products, conditions for the alkylation of other carbonyl compounds alkylation reaction
    Write the reactants, products, conditions for the alkylation (acylation) of enamines alkylation reaction
    Write the reactants, products, conditions for the aldol and crossed aldol condensation carbanion reaction
    Write the reactants, products, conditions for the Claisen and crossed Claisen condensation carbanion reaction; Michael addition; Robinson annulation
    Write the reactants, products, conditions for the Michael addition carbanion reaction

  35. Summarize the names and formulas for amines
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the correct names for amines
    Write the correct names for ammonium salts
    Draw the correct structures of amines
    Draw the correct structures of ammonium salts

  36. Determine physical properties of amines
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Summarize the trends in solubility for amines and ammonium salts
    Summarize the trends in boiling point for amines and ammonium salts
    Summarize the trends in density for amines and ammonium salts
    Relate hydrogen bonding to the solubility of amines
    Relate hydrogen bonding to the boiling point of amines

  37. Identify spectral characteristics of amines
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Identify characteristics of amines in NMR
    Identify characteristics of amines in IR

  38. Explain the methods to synthesize amines
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products and conditions for the following reactions to synthesize amines: ammonia + alkyl halide
    Write the reactants, products and conditions for the following reactions to synthesize amines: Gabriel synthesis
    Write the reactants, products and conditions for the following reactions to synthesize amines: reduction of nitro compounds
    Write the reactants, products and conditions for the following reactions to synthesize amines: nitriles
    Write the reactants, products and conditions for the following reactions to synthesize amines: amides
    Write the reactants, products and conditions for the following reactions to synthesize amines: reductive amination
    Write the reactants, products and conditions for the following reactions to synthesize amines: Hofmann rearrangement

  39. Predict products of amine reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the reactants, products, conditions for the following reaction of amines with acids
    Write the reactants, products, conditions for the following reaction of amines with enzenesulfonyl chloride
    Write the reactants, products, conditions for the following reaction of amines with nitrous acid
    Write the reactants, products, conditions for the following reaction of ammonium salts with base
    Write the reactants, products, conditions for the following reaction of ammonium salts with silver oxide
    Write the reactants, products, conditions for the following reaction of ammonium salts with heat (ammonium hydroxides)
    Write the reactants, products, conditions for the following reaction of ammonium salts with exhaustive methylation

  40. Compare acid-base properties of amines
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Compare the acidity of amines with other basic organic compounds

  41. Summarize the names and formulas for polycyclic and heterocyclic aromatic ompounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Write the correct names/formulas for naphthalene
    Write the correct names/formulas for anthracene
    Write the correct names/formulas for phenanthrene
    Write the correct names/formulas for pyridine
    Write the correct names/formulas for pyrrole
    Draw correct structure for naphthalene
    Draw correct structure for anthracene
    Draw correct structure for phenanthrene
    Draw correct structure for pyridine
    Draw correct structure for pyrrole

  42. Compare acid-base properties of heterocyclic aromatic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Compare the acidity/basicity heterocyclic amines with other acidic and basic organic compounds

  43. Explain the theory of UV and mass spectrometry
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Explain the relationship of energy, absorbance and molar absorptivity
    Identify UV energy states
    Explain IR active molecular vibrations
    Explain how a mass spectrometer works
    Relate magnetic states of nuclei to NMR

  44. Interpret IR, NMR, UV and mass spectra
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material; with periodic table and other tables and/or charts as provided
    Criteria
    Identify major functional parts in spectra.
    Summarize energy transitions
    Summarize compounds that absorb in UV-VIS
    Summarize lambda max
    Summarize functional groups present and absent
    Summarize different proton environments and number of protons
    Summarize different C environments
    Summarize molecular ions
    Summarize fragmentation patterns
    Summarize isotopic patterns
    Propose structures for compounds using information above