The Diels–Alder reaction between anthracene and maleic anhydride

The Diels–Alder reaction between anthracene and maleic anhydride

 

 

 

Pre-laboratory assignment (Due on Blackboard Monday, April 27 2020

Link to video: https://www.youtube.com/watch?v=HdvrTQpzfjc

 

  1. Complete the following table with the amounts presented in the video:

 

Reagent Molecular weight (g/mol) Density (g/mL) Moles Mass (g) Volume (mL) Role in the reaction
Anthracene   —     —  
Maleic anhydride   —     —  
Xylenes     — —    

 

  1. Draw the product for each of the following Diels–Alder reactions:

 

  1. List the precautionary measures that you will take when handling xylenes.
  2. Calculate the theoretical yield of the product.
  3. Summarize a procedure (250 words or less) based on the instructional video.

 

 

 

 

Report:

Include the name of all group members and the experiment name

Draw the reaction scheme (use ChemDraw)

 

  1. Draw and discuss the mechanism for the formation of the Diels-Alder adduct of anthracene and maleic anhydride.

 

  1. Tabulate 3-5 relevant IR peaks for the Diels–Alder reaction product.

 

  1. Compare and contrast the IR spectra of your starting materials (anthracene and maleic anhydride) and product (9,10-dihydroanthracene-9,10-a,b-succinic anhydride) and explain how the IR data for the product confirms the formation of the Diels-Alder adduct. Pay special attention to the carbonyl stretching frequencies.

 

  1. Show your calculations for the theoretical yield of the product. Include calculations for the moles of each reactant.

 

 

 

 

GRADING SCHEME FOR DIELS-ALDER REACTION

Format/Title                                                                                                   2 points

Reaction Scheme                                                                                            2 points

Discussion questions                                                                                     25 points

Calculations                                                                                                   3 points

Grammar                                                                                                        3 points

Total                                                                                                               35 points

 


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