Academic Catalog

CHEM 13BH: HONORS ORGANIC CHEMISTRY LABORATORY

Foothill College Course Outline of Record

Foothill College Course Outline of Record
Heading Value
Effective Term: Summer 2021
Units: 3
Hours: 1 lecture, 6 laboratory per week (84 total per quarter)
Prerequisite: CHEM 12A and CHEM 12AL.
Corequisite: CHEM 12B.
Advisory: Not open to students with credit in CHEM 12BL.
Degree & Credit Status: Degree-Applicable Credit Course
Foothill GE: Non-GE
Transferable: CSU/UC
Grade Type: Letter Grade Only
Repeatability: Not Repeatable

Student Learning Outcomes

  • Interpret experimental data through application of theoretical models
  • Safely handle Organic Chemicals
  • Gain skill with common synthetic chemistry techniques

Description

Honors laboratory course to accompany CHEM 12B. Intended to introduce students to laboratory techniques common in modern synthetic organic chemistry. Emphasis is on chemical reactions relevant to CHEM 12B content. Similar to CHEM 12BL, this honors course adds critical analysis of primary literature, and requires additional writing assignments and group presentations.

Course Objectives

The student will be able to:
A. Safely handle and dispose of hazardous chemicals
B. Execute techniques common to chemical researchers in order to synthesize, isolate, purify and characterize organic compounds
C. Gain skill in the critical evaluation of primary literature
D. Provide a rationale for each step in an experimental design
E. Analyze data to draw conclusions about chemical system
F. Communicate effectively using the language of Organic Chemistry
G. Work constructively and collaboratively in groups

Course Content

A. Safely handle and dispose of hazardous chemicals (refer to Lab Content)
B. Execute techniques common in experimental chemistry to synthesize, isolate, purify and characterize organic compounds. (refer to Lab Content)
C. Critically evaluate primary literature on topics relevant to CHEM 12B (e.g., Nuclear Magnetic Resonance, Electrophilic Aromatic Substitution, Organometallics, Asymmetric Synthesis, Multistep Synthesis, Kinetics vs Thermodynamics)
1. Review how research results are disseminated
2. Examine components of a research article
3. Link experimental results to current theory
4. Analyze data to formulate conclusions
a. Deduce whether or not data supports a hypothesis
b. Relate graphical displays to current theoretical models
c. Evaluate and discuss experimental results
d. Propose next steps in scientific inquiry
5. Present and justify deductive reasoning to support experimental results
D. Analysis of experimental design
1. Rationalize the approach taken to address a scientific inquiry
2. Determine the need for each step taken in a scientific inquiry
3. Predict the consequence of a given experimental outcome
E. Data analysis and precision/error assessment (refer to Lab Content)
F. Effective communication using the language of Organic Chemistry
1. Group Work
2. Poster and/or Oral Presentation of topic of interest related to course content
G. Work constructively and collaboratively in groups

Lab Content

A. Safely handle and dispose of hazardous chemicals
1. Research and report published safety data sheets on all chemicals being manipulated
2. Categorize and segregate hazardous waste to avoid undesired reaction between incompatible compounds
3. Apply care and skill in following instruction to safely handle hazardous compounds
B. Practice common laboratory techniques to acquire skill in the preparation, isolation and purification of Organic compounds using guided inquiry laboratory projects as exemplified below:
1. Multi-step syntheses of 4-Bromoaniline from Aniline
2. Bromination of trans-cinnamic acid
3. Selective reduction of 3-nitroacetophenone
4. The Diels-Alder reaction between butadiene and maleic anhydride
5. Acid-Catalyzed Dehydration of 3-methylcyclohexanol
6. Identification of Organic Compounds
a. Measure Physical Properties (mp or bp, mixed mp)
b. Identification of unknowns by NMR
c. Acquisition of FTNMR (1H or 13C) and/or FTIR spectra on isolated products
7. Isolation/Purification of Organic Compounds
a. Column Chromatography as needed
b. TLC to follow reaction progress and assess purity
b. Distillation (microscale to remove solvent, steam to isolate product)
d. Routine Extraction and Recrystallization
e. Gas Chromatographic separation of products from Acid-Catalyzed Dehydration of 3-methylcyclohexanol
f. Assessing the optimal method for isolation or purification of an impure organic compound
C. Demonstrate skill in the evaluation of primary literature (refer to Course Content)
D. Analysis of experimental design (refer to Course Content)
E. Data analysis and precision/error assessment
1. Computing margins of error in volume, weight and chromatographic signal integration measurements
2. Propagation of error in computation
F. Effective communication using the language of Organic Chemistry
1. Group work
2. Laboratory notebook preparation
3. Formal laboratory report
4. Maintenance of complete and accurate records of experiments
G. Work constructively and collaboratively in groups

Special Facilities and/or Equipment

Standard and Microscale Chemistry Glassware, MP apparatus, Analytical Balance, GC, FT NMR, FTIR, Library resources including access to research publications in Chemistry.

Method(s) of Evaluation

Evaluations include but are not limited to:
A. Participation in execution of laboratory
B. Short answer examinations
C. Data analysis and written laboratory reports
D. Demonstration of safety protocols

Method(s) of Instruction

During periods of instruction the student will be:
A. Engaged in the preparation, isolation and purification of organic compounds
B. Working in groups to analyze data published in primary literature
C. Presenting his or her experimental results to the class

Representative Text(s) and Other Materials

Mohrig, Jerry R. Laboratory Techniques in Organic Chemistry: Supporting Inquiry-driven Experiments. New York, NY: W.H. Freeman, 2014.
 

Types and/or Examples of Required Reading, Writing, and Outside of Class Assignments

Required reading and writing may include:
A. Analyzing research article to extract information relevant to stated conclusions, and demonstrating acquired knowledge in writing.
B. Organizing and reporting of experimental results in formal laboratory report.
C. Formulation of abbreviated outline from detailed experimental procedure.
 

Discipline(s)

Chemistry