20806256Organic Chemistry 1 Lecture
Course Information
Description
The first semester of a two-semester organic chemistry sequence. Includes the electronic structure and bonding of atoms and molecules; the nomenclature, mechanisms, reactions and properties of the following classes of compounds - alkanes, alkenes, alkynes, alkyl halides, alcohols, ethers, thiols, and sulfides; instrumental (IR, NMR) methods of analysis and their interpretation. Includes a three hour per week laboratory component as well as four hours per week lecture/discussion.The first semester of a two semester organic chemistry sequence. Includes the electronic structure and bonding of atoms and molecules; stereochemistry; acids and bases; oxidation and reduction; the nomenclature, reactions, and properties of the following classes of compounds - alkanes, alkenes, alkynes, alkyl halides, alcohols, ethers, and epoxides. Includes the theory and interpretation of IR spectrophotometry and mass spectrometry.
Total Credits
4
Course Competencies
  1. Explain the characteristics of atoms that relate to chemical bonding
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided when necessary.
    Criteria
    Write and interpret electronic configurations
    Write and interpret electron dot symbols
    Recognize electronegativity trends in the periodic table
    Recognize atomic radius trends in the periodic table
    Identify the number of covalent bonds that nonmetallic elements usually form
    Identify atomic orbitals
    Recognize the differences between ionic and covalent bonds
    Calculate the formal charge on an atom or ion
    Recognize the importance of electronegativity and polarizability in the formation of polar covalent bonds

  2. Explain the characteristics of molecules that relate to chemical bonding
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Predict the types of bonds for a compound formed from specific atoms
    Predict the formula for a compound formed from specific atoms
    Write Lewis and line bond structures for molecules
    Use arrow and half-arrow (fishhook) symbols to show the movement of electrons
    Use both the crossed arrow and delta symbols to represent a polar bond
    Identify the properties of sigma and covalent bonds

  3. Explain the characteristics of molecules that relate to physical properties
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Compare the following intermolecular forces: dipole-dipole interactions, London forces, hydrogen bonding
    Relate intermolecular forces to solubility characteristics of molecules
    Relate intermolecular forces to boiling points of molecules
    Relate intermolecular forces to shapes of molecules

  4. Compare acid-base properties of organic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Identify the properties of strong acids
    Identify the properties of strong bases
    Identify the properties of weak acids
    Identify the properties of weak bases
    Calculate and interpret the meaning of Ka
    Calculate and interpret the meaning of Kb
    Calculate and interpret the meaning of pKa
    Calculate and interpret the meaning of pKb
    Write the formulas for conjugate acids
    Write the formulas for conjugate bases
    Summarize the strength relationship of conjugate acid-base pairs
    Identify the characteristics of acids and bases in the Arrhenius theory
    Identify the characteristics of acids and bases in the Bronsted-Lowry theory
    Identify the characteristics of acids and bases in the Lewis theory
    Identify organic acid functional groups
    Identify organic base functional groups

  5. Explain the role of orbitals in chemical bonding
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Identify the properties of sigma and pi covalent bonds
    Complete a molecular orbital diagram
    Identify the hybridization and geometries of atoms in molecules or ions
    Relate resonance to the characteristics of benzene
    Write resonance forms
    Identify resonance forms as major or minor contributors

  6. Explain the characteristics of molecules that relate to their orbital interactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Identify orbitals involved in bonds
    Relate hybridization to bond length
    Identify functional groups
    Identify and use the symbolism –R (alkyl) and Ar (aryl)
    Identify the polarity and bonding in a carbonyl group
    Identify conjugated double bond systems in a molecule
    Identify cumulative double bond systems in a molecule
    Identify isolated double bond systems in a molecule
    Explain how conjugated systems allow for delocalization of electrons
    Use appropriate symbols to represent resonance structures
    Relate resonance to the acidity of organic compounds

  7. Interpret different types of chemical formulas
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write and interpret the following for molecules: Lewis structures
    Write and interpret the following for molecules: molecular formula
    Write and interpret the following for molecules: empirical formula
    Write and interpret the following for molecules: complete structural formula
    Write and interprets the following for molecules: condensed formula
    Write and interprets the following for molecules: skeletal formula
    Write and interprets the following for molecules: line angle formula
    Interpret the following for molecules: 3-dimensional representations of types

  8. Predict products for alkane reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write halogenation reactions for saturated hydrocarbons
    Write combustion reactions for saturated hydrocarbons

  9. Determine physical properties of hydrocarbons
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Identify the trends in solubility for alkanes and cycloalkanes
    Identify the trends in boiling point for alkanes and cycloalkanes
    Identify the trends in density for alkanes and cycloalkanes

  10. Identify the names and formulas for alkanes, cycloalkanes and substituted alkanes
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Identify structures of isomers
    Draw the structures of isomers
    Write the correct names for alkanes
    Write the correct names for cycloalkanes
    Write the correct names for cycloalkanes derivatives
    Draw correct structures for organic compounds (alkanes, cycloalkanes, alkyl halides)
    Name and/or draw the structure for the methylene group
    Name and/or draw the structure for the phenyl group
    Name and/or draw the structure for the benzyl groups
    Name and/or draw the structure for the nitro group
    Name and/or draw the structure for the chloro group
    Name and/or draw the structure for the bromo groups
    Name and/or draw the structure for the iodo group
    Name and/or draw the structure for the fluoro group
    Name and/or draw the structure for the methyl group
    Name and/or draw the structure for the ethyl group
    Name and/or draw the structure for the propyl group
    Name and/or draw the structure for the butyl group

  11. Determine the stereochemistry of organic compounds
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write and interpret 3-dimensional structures using wedge/dash
    Write and interpret 3-dimensional structures using sawhorse
    Write and interpret 3-dimensional structures using Fischer projections
    Write and interpret 3-dimensional structures using Newman projections
    Identify molecules that are: cis or trans; E or Z; R or S
    Use Newman projections to relate conformations to energy in molecules
    Relate heat of combustion data to the concept of ring strain
    Write conformations for small cycloalkanes
    Identify axial and equatorial positions on cyclohexane
    Identify chiral carbons and their relationship to enantiomers
    Identify chiral carbons and their relationship to diastereomers
    Identify chiral carbons and their relationship to meso forms
    Explain how a polarimeter functions and the type of information it provides
    Use appropriate symbolism to indicate an optically active compound
    Summarize formulas for chiral compounds
    Summarize ways to resolve racemic mixtures
    Explain the concept of prochirality

  12. Determine the stereochemistry of substitution and elimination reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Explain the stereochemical factors in SN1 reactions
    Explain the stereochemical factors in SN2 reactions
    Explain the stereochemical factors in E1 reactions
    Explain the stereochemical factors in E2 reactions

  13. Summarize the steps in substitution and elimination mechanisms
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Draw and interpret energy diagrams for substitution and elimination reactions
    Explain the kinetics of substitution and elimination reactions
    Write mechanisms for substitution and elimination reactions
    Predict products of hydride and alkide shifts
    Explain the rates of allylic and benzylic reactions
    Explain the kinetic isotope effect

  14. Predict products of substitution and elimination reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Summarize reactants and products for substitution and elimination reactions
    Indicate trends in halogens as leaving groups
    Identify factors that lead to substitution and elimination reactions
    Compare nucleophilicity and basicity
    Identify factors that affect the rate of substitution and elimination reactions
    Predict Saytzeff/Hofmann ratios of products in elimination reactions
    Predict cis/trans ratios of products in elimination reactions

  15. Determine physical properties of alkyl halides
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Identify the trends in solubility for halogenated alkanes
    Identify the trends in boiling point for halogenated alkanes
    Identify the trends in density for halogenated alkanes

  16. Identify the names and formulas for alkyl halides
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write correct names for alkyl halides
    Draw correct structures for alkyl halides
    Summarize alkyl halides
    Summarize ary halides
    Summarize vinyl halides
    Summarize methy halides
    Summarize primary halides
    Summarize secondary halides
    Summarize tertiary halides

  17. Predict products for free radical reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Predict the product(s) of free radical substitution reactions of chlorine
    Predict the product(s) of free radical substitution reactions of bromine
    Identify the relative reactivities of chlorine in free radical reactions
    Identify the relative reactivities of bromine in free radical reactions
    Write products of NBS with alkenes
    Summarize products of reactions of alkenes with oxygen
    Predict monomer and/or polymer structures

  18. Summarize the mechanisms for free radical reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write initiation, propagation and termination steps of individual and polymerization reactions
    Summarize the relative stability of free radical intermediates
    Show peroxides as free radical initiators
    Show phenols as free radical inhibitors
    Write resonance structures for free radical intermediates

  19. Determine the stereochemistry of free radical reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Explain the stereochemistry of free radical reactions

  20. Compare acid-base properties of alcohols
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Show alcohols as acids and bases

  21. Outline mechanisms for reactions of alcohols
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Outline the Grignard/organolithium reactions with carbonyl compounds mechanism
    Outline the hydrogen halides with alcohols mechanism
    Outline the tosylate esters with nucleophiles mechanism
    Outline the thionyl chloride with alcohols mechanism
    Outline the dehydration of alcohols mechanisms

  22. Predict products of alcohol reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Draw products for the following reactions of alcohols with: halides, thionyl chloride, phosphorus tribromide, acids, oxidizing agents, reducing agents
    Draw products for the reaction of alcohols with halides
    Draw products for the reaction of alcohols with thionyl chloride
    Draw products for the reaction of alcohols with phosphorus tribromide
    Draw products for the reaction of alcohols with acids
    Draw products for the reaction of alcohols with oxidizing agents
    Draw products for the reaction of alcohols with reducing agents
    Summarize the relative reactivities of hydrogen halides with alcohols
    Solve synthesis problems involving alcohols
    Identify oxidation and reduction in organic reactions

  23. Determine physical properties of alcohols
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Relate hydrogen bonding to the solubility of alcohols
    Relate hydrogen bonding to the boiling point of alcohols

  24. Write names and formulas for alcohols
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write the correct names for alcohols and diols
    Write the correct structures for alcohols and diols
    Identify alcohols as primary, secondary, and tertiary

  25. Outline methods to synthesize alcohols
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Predict products for the reaction of alkyl halides and hydroxide
    Predict products for the reaction of reduction of carbonyl compounds
    Predict products for the reaction of hydration of alkenes
    Predicts products for the reaction of Grignard and Lithium reagents with carbonyl compounds, water
    Predicts products for the reaction of alkyl halides and magnesium or lithium

  26. Compare acid-base properties of ethers, epoxides, and sulfides
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Compare the acidity of alcohols and thiols

  27. Outline mechanisms for reaction of ethers, epoxides, and sulfides
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Indicate mechanisms for the following reactions: Williamson ether synthesis
    Indicate mechanisms for the following reactions: alkene + peroxyacid
    Indicate mechanisms for the following reactions: intramolecular reaction of halohydrins
    Indicate mechanisms for the following reactions: epoxide cleavage with acid and/or base
    Indicate mechanisms for the following reactions: ethers and HI and/or HBr
    Indicate mechanisms for the following reactions: sulfides by SN2

  28. Predict products of ethers, epoxides, and sulfide reactions
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write reactants, products, conditions for the following reactions :ethers and HBr or HI
    Write reactants, products, conditions for the following reactions: acid/base catalyzed cleavage of ethers
    Write reactants, products, conditions for the following reactions: Grignard + epoxide
    Write reactants, products, conditions for the following reactions: Williamson ether synthesis
    Write reactants, products, conditions for the following reactions: intermolecular dehydration of alcohols
    Write reactants, products, conditions for the following reactions: thiol + strong base
    Write reactants, products, conditions for the following reactions: alkyl halide + bisulfide.
    Write reactants, products, conditions for the following reactions: alkyl halide + alkyl sulfide
    Write reactants, products, conditions for the following reactions: oxidation of thiols and sulfides
    Write reactants, products, conditions for the following reactions: reduction of disulfides.

  29. Determine physical properties of ethers, epoxides, and sulfides
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Summarize the trends in solubility for ethers and sulfur containing organic compounds
    Summarize the trends in boiling point for ethers and sulfur containing organic compounds
    Summarize the trends in density for ethers and sulfur containing organic compounds
    Relate hydrogen bonding to the solubility of ethers and sulfur containing organic compounds
    Relate hydrogen bonding to the boiling point of ethers and sulfur containing organic compounds

  30. Write names and formulas for ethers, epoxides, and sulfides
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write the correct names for ethers
    Write the correct names for epoxides
    Write the correct names for oxiranes
    Write the correct names for thiols
    Write the correct names for sulfides
    Draw the correct structure for ethers
    Draw the correct structure for epoxides
    Draw the correct structure for oxiranes
    Draw the correct structure for thiols
    Draw the correct structure for sulfides

  31. Outline methods to synthesize ethers, epoxides, and sulfides
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write the reactants, products and conditions for the following reaction: dehydration of alcohols
    Write the reactants, products and conditions for the following reaction: Williamson ether synthesis
    Write the reactants, products and conditions for the following reaction: alkene + peroxyacid
    Write the reactants, products and conditions for the following reaction: intramolecular reaction of halohydrins

  32. Interpret IR and NMR spectra
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Identify major functional groups in spectra
    Explain the effects of hydrogen bonding
    Explain the shielding effects
    explain the inductive and anisotropic effects
    Identify chemically equivalent hydrogens
    Identify relative areas
    Identify splitting patterns
    Identify compounds that produce spectra for IR
    Identify compounds that produce spectra for proton NMR
    Identify compounds that produce spectra for carbon-13 NMR
    Calculate unsaturation number (double bond equivalents) for a compound

  33. Explain the theory of IR and NMR
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Explain the relationship of energy, wavelength, frequency
    Identify IR vibrational states
    Explain how IR and NMR instruments work
    Relate magnetic states of nuclei to NMR

  34. Compare acid-base properties of alkenes and alkynes
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Compare the relative acidity of a terminal alkyne with other organic functional groups

  35. Summarize the mechanisms for reactions of alkenes and alkynes
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Outline the mechanisms for the following reaction: addition of acids to alkenes
    Outline the mechanisms for the following reaction: Markovnikov and anti-Markovnikov
    Outline the mechanisms for the following reaction: oxymercuration­demercuration
    Outline the mechanisms for the following reaction: hydroboration, carbene addition;
    Outline the mechanisms for the following reactions: Simmons-Smith reaction
    Draw energy diagrams to explain: Markovnikov addition; effect of a catalyst

  36. Predict products of reactions of alkenes and alkynes
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Indicate reactants, products and conditions for the following reaction: terminal alkyne + sodamide and/or Grignard
    Indicate reactants, products and conditions for the following reaction: addition of acids, halogens, hydrogen to alkenes and alkynes
    Relate heats of hydrogenation to alkene stability
    Indicate products and conditions for the reaction of alkenes and alkynes with potassium permanganate
    Indicate products and conditions for the reaction of alkenes and alkynes with osmium tetroxide
    Indicate products and conditions for the reaction of alkenes and alkynes with sodium bisulfite
    Indicate products and conditions for the reaction of alkenes and alkynes with peroxycarboxylic acids
    Indicate products and conditions for the reaction of alkenes and alkynes with oxygen
    Indicate products and conditions for the reaction of alkenes and alkynes with ozone

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

  38. Identify the names and formulas for alkenes and alkynes
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Write correct names for alkenes and alkynes
    Draw correct structures for alkenes and alkynes

  39. Summarize the methods to synthesize alkenes and alkynes
    Assessment Strategies
    Minimum score of 70% on written exams and quizzes without referring to text and/or other reference material and with relevant tables and/or charts as provided.
    Criteria
    Use the E2 reaction of alkyl halides and vicinal dihalides method to synthesize alkenes and alkynes
    Use the acetylides + alkyl halides method to synthesize alkenes and alkynes
    Use the Grignard + carbonyl compound method to synthesize alkenes and alkynes