Diels-Alder Cycloaddition

Diels-Alder Cycloaddition Reaction Report Guidelines

Purpose: (5 pts)

• Provide a brief explanation of the purpose of this experiment. Do not exceed three sentences.  Do not start the first sentence with the word: To.

Reaction Scheme: (5 pts)

• Chemdoodle reaction scheme (Included student name)

Procedure (10 pts)

• Used prototypical procedures as explained on pg 60. Address the particularities of this experiment.

Data, Calculations, and Results (20 pts)

• Table of IR data (see Aspirin synthesis report sheet for an example). (10 pts)
• Show limiting reactant calculations (to product mass) (5 pt)
• Show percent yield calculations based on limiting reactant. (5 pt)

Results and Discussion (15 pts)

• Discuss the purity of your product. (5 pts)
• Characterize your product by IR (5 pts)

Conclusion (15 pts)

• Summarize the experiment.
• Did you make the correct product? Make sure to use all of the data to justify your conclusion.  Be specific in your justification.Just saying that it looks good is not an answer.  A good answer includes a full comparison of the literature and experimental IR data.

References (2 pt)

• Lab manual
• Anything else. Lab manual or ACS format should be maintained.

Mechanism (25 pts) – attach to end of report, turn in a paper copy to TA.

• Draw the mechanism for the Diels-Alder cycloaddition between 1,3-butadiene and maleic anhydride. (10 pts)
• Propose a mechanism for the opening of the product anhydride (cis-4-cyclohexene-1,2-dicarboxylic acid) under acidic conditions to render a dicarboxylic acid product. (15 pts)

Literature Search (8 pts)

• The Diels-Alder synthesis is an important tool for chemical synthesis. Please provide another example of this type of synthesis from recent literature.  Narrow your search to these journals: Journal of the American Chemical Society, Journal of Medicinal Chemistry, Journal of Organic Chemistry, and Organic Letters and limit your search to articles published within the past 8 years.  Include a proper ACS formatted reference and upload a pdf copy of the article with your report.  (Note: use the university library’s remote access portal to access the ACS journal website.)