Four isomeric (C₅H₁₀O₂) liquids are found in separate bottles with no labels. We shall refer to these unknowns as A, B, C, & D. These compounds are known to have the structures shown on the right. Each of these compounds is partially or completely soluble in water, and is also soluble in ether and methylene chloride.
To discover which is which, three chemical tests may be applied to these unknowns:

1. Treatment with 5% aqueous sodium bicarbonate (NaHCO₃ ).
2. Treatment with Tollens' reagent (AgNO₃ in NH₄OH ) .
3. Treatment with Jones' reagent (CrO₃ in H₃O⁽⁺⁾ ).

Once you have conducted your tests, make structural assignments to A, B, C & D in the boxes following the compound names.