Hypotheses

=Hypotheses= 1. Aromatic aldehydes with electron withdrawing groups form a significant amount of hemi-acetal (>5%) when dissolved in pure alcohols. (Discoveries 1 and 2 UsefulChem post ) **JC Bradley** 2. Water will form a hydrate with 4-chlorobenzaldehyde based on the behavior of ethanol and methanol (Discoveries 1 and 2). Because the very low solubility of this aldehyde in water (0.005 M ) it may be possible to observe the formation of the hydrate in a solvent such as acetonitrile, which easily dissolves the aldehyde and water without reacting. **JC Bradley** 3. By the difference in NMR shift it should be possible to distinguish between pure bulk water, water in a brine environment and water dissolved in octanoic acid. This would allow a direct measurement of the desalination process in a single NMR session cycling from 25C to 60C and back. (see Ref 1 ) **JC Bradley** 4. Acetonitrile inhibits 4-chlorobenzaldehyde from forming hemiacetals **Cuepil** 5. ethanol produces less hemiacetal production than methanol due to the larger molecule having a less favorable chance of meeting the aldehyde with the hydroxy group head on **Cuepil** 6. Only cyclic acetals can form upon heating of diols with aromatic aldehydes and no catalyst. **JCB** 7. The benzylic HNMR peak and the OH HNMR peak of 4-chlorobenzaldehyde hemiacetal couple only at lower temperatures. At higher temperatures, only the benzylic singlet is visible. CRSEXP007 array table shows coupling only at room temperature. **Cuepil**