Jitin Varughese Chem 2204 September 17, 2012 The Diels-Alder Reaction of Furan and Maleic Anhydride Objective:

The purpose of this experiment is to review and practice recrystallization techniques. The Diels-Alder reaction helps to create products and solvents.
Reaction Scheme:

Data and Results Table: AlphaPhellandrene Mol. Formula Amount (g) Amount (mL) mmoles Molar (g) Mass 0.500 6.88 136.24 0.77 6.80 4 M in CH2Cl2 234.29 2.0 C10H16 maleic anhydride C4H2O3 CH2Cl2 exo-product C14H18O3 endo-product C14H18O3al

Density (g/ml) mp (C) lit. mp (C)

0.838 113 110

Calculations: .8380g of alpha phellandrene * .5mL * 1 mole * 1000 * 1 = 1.77 ml phellandrene mL 136.24g phellandrene 4 M of Phellandrene Observations:

Errors

There were no changes seen in the reaction tube even though the tube was kept for recrystallization for 2 weeks. To recrystallize the solution a glass rod was used to dip in the solution and that made the solution recrystallize within a few minutes. White needle like substance was formed. The reaction was exothermic as heat was formed on the test tube. The room temperature and exposure to air made the recrystallization process faster.

The reason that the solution was not recrystallized for two weeks maybe cause it was not mixed in unclean test tube. the other reason that it was not recrystallized can be because of the temperature where the test tube was kept for 2 weeks. Questions

I. Questions: Answer the following questions. Be as complete as possible, and always explain your reasoning. 1. Write a mechanism for the Diels-Alder reaction of furan and maleic anhydride. Include pathways to all possible products and be sure to show electron flow. The first question in every lab report will always pertain to reaction mechanism.

2. After recrystallization, did you isolate the exo- or endo-isomer of the Diels-Alder product? What data supports your assignment? After recrystallization I was able to isloate the exo isomer as the melting point was from 110 to 115C.The melting point of an endo isomer of diels alder reaction is 80C while that of exo isomer is going to be 114C

3. When forming bicyclic products in a Diels-Alder reaction, explain why the endoproduct is favored in most cases (hint: your response should include mention of molecular orbitals). Is your recrystallized product (question 2) in line with this trend, or an exception? In bystolic product formed in a Diels-Alder reaction in most cases would be an endoproduct. The highest occupied molecular orbital (HOMO) of the diene will donate electron density into the lowest unocupied molecular orbital (LUMO) of the dienophile results in cyclic product and non polar transition state. The isomer I got through

recrystalliztion is an exo isomer which is an exception but exo isomers are generally stable than endo isomers.

4. Does the identity of your recrystallized product agree with your expectations from the energy calculations performed in the SPARTAN experiment?

5. Draw the structures for the diene and dienophile necessary to synthesize bicyclo[2.2.2]oct-2-ene by a Diels-Alder reaction:

bicyclo[2.2.2]oct-2-ene