In terms of the molecular complexity of the product, why might a “tandem reactio
ID: 1032621 • Letter: I
Question
In terms of the molecular complexity of the product, why might a “tandem reaction” like this be an attractive method to develop?
Experimental Procedure: Using the appropriate pipet, carefully transfer 50 ?L of (E,E)- 2,4-hexadien-1-ol into the bottom of a clean, dry, tared small beaker (<100 mL, the smaller the better!). After the transfer, weigh your beaker. Add an equimolar amount of finely powdered, solid maleic anhydride (~44 mg) to the same beaker. Use the small end of a clean, dry metal spatula to vigorously and continuously stir the mixture as it liquefies and resolidifies (10-15 minutes). After solidification is complete, weigh the beaker and calculate the mass of product and yield. Analyze your product by IR (solid) and melting point (lit value reported to be 159-161°C).
?? no heat no solvent + enantiomer CO2H CH3 CH3 proton transfer CH3 CH3Explanation / Answer
The basic definition of a "tandem reaction" also called cascade reaction is when a series of reaction steps (minimum two) occur consecutively, solely on the basis of chemical functionality of the product formed in the previous step. The process is completely internal with its inherent functional groups driving the reaction. Major advantages of this methodology is;
1. No isolation of intermeditaes necessary as reaction proceeds sponataneously.
2. No reagents need to be added after the initial step for further consecutive steps to occur.
3. No waste generated.
4. High atom economy which is an important part of green chemistry concept.
5. Much less time and work required to carry out the reaction.
In terms of the given reaction, by course of a tandem reaction, the molecular complexity has increased substantially, especially from a stereochemical point of view, but via a very efficient and simple process. A large degree of complexcity has been achieved in one transformation. This would be otherwise quite cumbersome if a different methodology was used.
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