20806267Organic Chemistry 2 Lab
Course Information
Description
This course covers traditional material taught in Organic Chemistry, as well as basic organic laboratory techniques, including correct documentation of work in a laboratory notebook, thin layer chromatography, distillation, recrystallization and separations. It will also include various characterization techniques, including NMR, IR, gas chromatography, melting point determination, and refractometry. Lastly, it will cover many of the organic transformations and mechanisms covered in most basic organic chemistry lecture courses, including polymerizationn, Diels-Alder, Aldol, Grignard syntheses, green chemistry, unknown characterization with multiple techniques and multi-step synthesis. This course will also include written and oral presentation components.
Total Credits
2
Course Competencies
  1. Document lab experiments in a standard format in a laboratory notebook
    Assessment Strategies
    Lab assignments
    Criteria
    The notebook contains an accurate and complete index
    The notebook includes an experimental objective, introduction with relevant theory and reaction schemes, chemical safety and disposal information, an accurate table of reference data, procedural details, and all necessary data tables prior to the beginning of each experiment
    Each completed experiment is accurately documented
    Each experiment's report is complete
    All sections of each report are substantive and accurate
    Each report includes a concise discussion indicating whether or not the experimental objective was met based on experimental results
    The information given in the notebook is sufficient to allow another individual with comparable skill and experience to replicate the experiment

  2. Perform single-step and multi-step syntheses of desired compounds
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    Substitution reactions (SN1 and SN2) are successfully performed on various substrates
    Elimination reactions (E1 and E2) are successfully performed on various substrates
    Alkylation of an aromatic compound is successfully performed
    A Diels-Alder product is successfully synthesized
    A [4 + 2] cycloaddition reaction similar to the Diels-Alder reaction is successfully performed
    An aqueous analog to the Grignard reaction is successfully performed
    A Fischer esterification reaction is successfully performed
    Reduction of a nitro derivative formed by thermal dehydration of an aromatic dicarboxylic acid with hydrazine is successfully performed
    Green chemistry concepts are explored and implemented

  3. Identify structures of unknown chemicals using NMR spectroscopy
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    NMR spectra include a complete, accurate and specific title
    NMR spectra include peaks labeled with relevant chemical shifts
    NMR spectra include peak integrations
    NMR spectra include the proposed structure consistent with the spectrum
    NMR spectra are accompanied by a table, detailing the chemical shifts, peak integrations, peak multiplicity, and peak labels Explanations are provided
    Explanations are provided for peaks that do not belong to the chemical that was synthesized

  4. Identify structures of unknown chemicals using infrared (IR) spectroscopy
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    IR spectra include a complete, accurate and specific title
    IR spectra include peaks labeled with relevant molecular vibrations
    IR spectra include the proposed structure consistent with the spectrum
    IR spectra are accompanied by a database match, along with percent similarity comparing the experimental spectra to reference spectra
    Matching peaks found in both the experimental and database spectra are highlighted

  5. Identify structures of solids using melting point analysis
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    The literature value for melting point of the pure substance is documented
    The melting range is correctly measured using a melting point apparatus
    The average melting range and melting “point” are correctly calculated based on experimental data
    The percent deviation between the experimental and literature melting points is correctly calculated based on experimental data
    A concise comparison of the experimental and reference melting point is included in the laboratory report
    The relative purity of the substance is assessed based on the width of the melting range and the percent deviation in the melting point

  6. Separate components from a liquid mixture using distillation techniques
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    A simple distillation apparatus is correctly assembled
    A fractional distillation apparatus is correctly assembled
    A mixture is successfully separated using simple distillation
    A mixture is successfully separated using fractional distillation
    Characterization techniques, such as thin layer chromatography, refractometry, infrared spectroscopy, gas chromatography and/or NMR spectroscopy are utilized to confirm identity and purity of isolated components from the mixture

  7. Separate components of a mixture using thin layer chromatography (TLC)
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    The retardation factor (Rf) of substances is accurately measured
    The percent deviation in the retardation factor is accurately calculated
    The components of a mixture are identified using standards
    The purity of a sample is assessed using the results of TLC analysis

  8. Identify an unknown chemical using refractometry
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    The refractive index of substances is accurately determined using a refractometer
    The experimentally measured refractive index is corrected to allow comparison to a reference refractive index
    The percent deviation in the refractive index is accurately calculated
    The corrected refractive index is used to confirm the identity of an unknown substance

  9. Identify components of a mixture using gas chromatography (GC)
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    Samples are prepared for injection into the gas chromatograph
    Samples are effectively analyzed using a gas chromatograph
    Accurate retention times are measured for each component of a mixture
    Accurate retention times are measured for standards of each potential component of a mixture
    The percent deviation in the retention time is accurately calculated
    The identity of each component in a sample is accurately identified
    The purity of a sample is assessed based on the experimental chromatogram

  10. Purify a sample using recrystallization
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    Determine appropriate recrystallization solvent(s) for a given sample
    Perform a recrystallization of a solid sample
    Recover the purified solid using vacuum filtration
    Perform appropriate analyses on the recrystallized solid to assess its purity

  11. Evaluate the purity of a final purified sample chemical
    Assessment Strategies
    Lab reports
    Pre-laboratory assessments
    Demonstrated lab performance
    Criteria
    Appropriate method(s) of analysis are chosen for a given sample
    A qualitative analysis of the purity of a sample is presented based upon the results of each method of analysis
    A quantitative analysis of the purity of a sample is presented based upon the results of each method of analysis

  12. Present current organic chemistry research reported in a scholarly journal
    Assessment Strategies
    Oral presentation
    Written summary
    Criteria
    Selected research is presented during an in-class presentation
    Presentation includes a title, outline, introduction, relevant theory, images, graphs or data tables as appropriate, conclusion and references
    Visual aids (PowerPoint, posters, etc.) are legible and appealing
    Presenter engages the audience
    Presenter discusses research using correct terminology
    Presenter is knowledgeable of all relevant details of presented research
    Presenter accurately answers fundamental questions posed during question-and-answer portion of presentation
    Presenter appropriately answers more advanced questions posed during question-and-answer portion of presentation
    An accurate summary of the research presentation is presented to the audience