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It is clear that there is a need for less expensive, and environmentally benign alternatives. The objective of this work is to develop a deeper understanding of the interaction between the solute (biomolecules) and the solvent, which is necessary to effectively choose these alternative solvents. A number of solvent properties like hydrogen bond formation, acidity, etc., will be studied for both imidazolium-based ILs and lower-cost alternatives. Using probe reactions like the isomerization and dehydration of sugars, property-performance relationships will be established. The effect of using different catalysts to affect the reaction environment and thence product yields will also be examined. This work will provide insights into rationally selecting ILs to perform targeted chemistries.