Distinguishing Isomers

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(+) ).

Isomer Treatment
with NaHCO3
with Tollens' reagent
with Jones' reagent

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

4-Hydroxytetrahydropyran ....  

2-Hydroxytetrahydropyran ....  

Isopropyl Acetate ....................  

2,2-Dimethylpropanoic acid ...  

This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.