Diels Alder Reaction Virtual Lab Simulation | PraxiLabs

Diels Alder Reaction Simulation

Chemistry | Organic Chemistry



As Featured In

General Aim

Synthesis of six member cyclic organic compounds.

Method

Electrocyclic reaction where 4 π-electrons from the conjugated diene (anthracene) and 2 π-electrons from the dienophile (maleic anhydride) are involved in the reaction in the presence xylene as a solvent at temperature of 350 ⁰C. The driving force is the formation of new σ-bonds as they are energetically more stable than the π-bonds.

Learning Objectives (ILO’s)

  • Become proficient at running organic chemical reactions.

  • Learning basics of organic synthesis procedures.

  • Understand mechanism of Diels Alder reaction.

  • Learn function of Diels Alder reaction Get trained on how reflux and setup of reaction is used.

Theoretical Background/Context

The Diels-Alder reaction is one of the most important reactions of organic chemistry since they are used in synthesizing six-membered ringed cyclic organic compounds.


It is also considered as a [4+2]-cycloaddition reaction because it involves the an addition reaction between a conjugated diene molecule and a substituted alkene (dienophile) in order to produce a substituted cyclohexene system. 


Specifically, 4 π-electrons from the conjugated diene and 2 π-electrons from the dienophile are involved in the reaction. Therefore, it is counted as an electrocyclic reaction whose driving force is the formation of new σ-bonds as they are energetically more stable than the π-bonds.


Furthermore, Diels-Alder reaction is known as a non-polar reactions since no charged intermediates are formed during the reaction. In addition, no unpaired electrons are involved in the addition reaction. It is considered as a concerted reaction since several bonds are formed and broken simultaneously during the transition state.

http://upload.wikimedia.org/wikipedia/en/6/68/Dielsalder.png

Principle of Work

An example of Diels Alder reaction is the cycloaddition of anthracene (conjugated diene) and maleic anhydride (dienophile) to form 9,10-dihydroanthracene-9,10-endo-a3-succinic anhydride. Xylene is used as the reaction solvent due to its high-boiling that could accommodate the high temperature needed for running the chemical reaction. 
Maleic anhydride is known as a highly reactive dienophile owing to the presence of two electron withdrawing carbonyl substituents within its chemical structure. On the other hand, anthracene is not a highly reactive diene because of both its steric hindrance in addition to its high stability due to aromaticity. 

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