The student will be able to:

1. Safely handle and dispose of hazardous organic chemicals
2. Acquire skill in laboratory techniques common to experimental organic chemistry
3. Acquire and interpret spectroscopic data, including NMR, IR, and GC-MS
4. Provide a rationale for each step in an experimental design
5. Analyze data to discern the validity of a hypothesis
6. Communicate clearly using the language of organic chemistry
7. Work constructively and collaboratively in groups

See Lab Content, below.

1. Safely handle and dispose of hazardous organic chemicals
   1. Research the Material Safety Data Sheets of chemicals
   2. Categorize chemicals according to their compatibility
2. Develop skill in laboratory techniques common to experimental organic chemistry. Representative projects may include the following or equivalent alternatives addressing similar outcomes:
   1. Aldol condensation-dehydration of unknown aldehydes and ketones
      1. Preparation, recrystallization and MP of ketone and aldehyde derivatives for unknown identification
      2. Characterization of aldol products via NMR and MP
   2. Ester synthesis via reaction between unknown alcohol and acetic anhydride
   3. Evaluation of the Keq for Fischer esterification of unknown alcohols
      1. Determination of relative response factors in GC
      2. NMR analysis of mixtures
   4. Amine synthesis via selective reduction of 3-nitroacetophenone
   5. Multi-step synthesis of bromoaniline from aniline; evaluation of regioselectivity
   6. Quantitative kinetics via NMR: evaluating substituent effects on the nucleophilic substitution of substituted benzyl chlorides
   7. Thermodynamic vs. kinetic control in the alkylation of chlorobenzene
   8. Combined spectroscopic identification of an unknown (MS, 1H NMR, IR)
3. Acquire and interpret spectroscopic data, including NMR, IR, and GC-MS
   1. Routine acquisition of 1H NMR and IR spectra following isolation of organic products
   2. Analysis of 1H NMR data. Applications may include but are not limited to:
      1. Acquisition of 13C NMR of organic unknowns
      2. Utilizing 1H NMR spectra to determine equilibrium constants between acetate esters and their associated alcohols
      3. Analyze GC-MS data of a general organic unknown to confirm its identity
4. Provide a rationale for each step in an experimental design
   1. Independent strategic planning of experimental procedures
   2. Evaluate procedural steps to identify consequences of errors and to propose alternative approaches
5. Analyze data to discern the validity of a hypothesis
   1. Determine the regioselectivity of a reaction through NMR analysis
   2. Formulate a strategy to deduce the identity of an unknown organic compound based on its properties and chemical reactivity alone
6. Communicate clearly using the language of organic chemistry
   1. Maintain complete and accurate records of experimental data and observations
   2. Prepare written laboratory reports
   3. Research and present chemical safety and handling precautions (SDS reports)

Critical evaluation of procedural steps in prelab exercises and/or quizzes
Demonstrating skill in safe handling of organic chemicals
Recording data and observations
Writing laboratory reports/ post lab summaries
Written short- answer examinations

Students will prepare, isolate, purify, and characterize organic compounds
Students will formulate hypotheses and critically evaluate the experiment designed to test it
Students will work with partner(s) to analyze experimental data
Students will draw conclusions based on first-hand experience
Students will discover the connection between experiment and real-world applications
Students will actively participate in instructor-led discussion of experimental design

Mohrig, Jerry, David Alberg, Gretchen Hofmeister, Paul Schatz, and Christina Noring Hammond. Laboratory Techniques in Organic Chemistry: Supporting Inquiry-driven Experiments. 2014.

Although this text is more than 5 years old, it is still in print and is a seminal text that describes laboratory methodology and techniques rather than providing prescriptive activities and is still therefore up to date.

1. Students will conduct a preliminary analysis of experimental procedures with the application of prior knowledge.
2. Students will evaluate and reflect on experimental results and summarize their findings in a post-lab report.
3. Students will draw their own conclusions based on first-hand observations and discuss them verbally and in writing.