The Diels- Alder Reaction 29 April 2009 Sulaiman Jacobs 2766456 Chemistry 211 Locker Number: D65 Instructor:

Babajide

Aim:

The main purpose of the experiment was to perform the Diels- Alder reaction between maleic anhydride and 1, 3-cyclopentadiene. The product was then converted to an acid.

Introduction:
The Diels- Alder reaction that was performed was a cycloaddition reaction of a conjugated diene and a dienophile. The main point of the reaction is the
formation of new -bonds, which are energetically more stable than the -bonds. With its broad applications and ease of operation, the Diels-Alder reaction is the most powerful synthetic method for unsaturated six-membered rings.

Materials and Method:

6.0g of maleic anhydride was dissolved to 20ml of ethyl acetate in a 125ml Erlenmeyer flask and was heated on a steam bath. 20ml of petroleum ether was added to the solution and it was cooled in an ice bath. The solution was kept in a homogenous state, and 6.0g of a 1, 3-cyclopentadiene was added to the flask

and whirled until the exothermic reaction subsided and the adduct had formed a white solid. The flask was placed back on the steam bath and heated until the product had redissolved. The flask was cooled to room temperature, where after it was filtered. The percentage yield and melting points were determined. 4.0g of the above product was added to an Erlenmeyer flask filled with 25ml of deionised water. The mixture was brought to a boil on a Bunsen burner until the initial oil that had formed had dissolved. The solution was cooled and crystallized. The crystals were filtered and the melting point and percentage yield was calculated.

Results:
Anhydride: Mass: 6.59g Melting Point: 1590C- 1600C Theoretical Yield: 6.0g + 4.80g = 10.80g Actual Yield = 6.59g % yield: 61.02 % Converted Anhydride: Theoretical Mass: 4.0g Actual Mass: 3.3g % Yield: 82.5% Melting Point: 1780C- 1790C

Discussion/ Exercise:
1. This is due to the fact that maleic anhydride contains electron withdrawing groups, this increases the reactivity. 2. This is to isolate the 1, 3-cyclopentadiene by fractional distillation. 3. The homogeneous solution helps determine the product of the reaction. 4. Each compound in the mixture could be easily identified and separated by layers.
5. 1, 3-cyclopentadiene was the limiting reagent; the amount of product

formed in the reaction was dependant on the amounts of 1, 3cyclopentadiene available. 6.

Conclusion:
The Diels-Alder reaction between 1, 3-cyclopentadiene and maleic anhydride

was performed, the melting points I obtained were with in range of the theoretical melting points, the yields obtained were also satisfactory, but could be bettered if the reaction was performed under ideal conditions.

References:
1. Roberts M, 1985, Modern Experimental Organic Chemistry, 4th edition,

chapter 15, Page 385-389. 2. http://www.organic-chemistry.org/namedreactions/diels-alderreaction.shtm