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Organic Chemistry Text Book (CHEM 3401 and 3402)

19.4.1a Hydration

It has been demonstrated (above) that water adds rapidly to the carbonyl function of aldehydes and ketones. In most cases the resulting hydrate (a geminal-diol) is unstable relative to the reactants and cannot be isolated. Exceptions to this rule exist, one being formaldehyde (a gas in its pure monomeric state). Here the weaker pi-component of the carbonyl double bond, relative to other aldehydes or ketones, and the small size of the hydrogen substituents favor addition. Thus, a solution of formaldehyde in water (formalin) is almost exclusively the hydrate, or polymers of the hydrate. Similar reversible additions of alcohols to aldehydes and ketones take place. The equally unstable addition products are called hemiacetals

R2C=O   +   R'OH      R'O–(R2)C–O–H   (a hemiacetal)


Stable Hydrates and Hemiacetals
To see examples of exceptional aldehydes and ketones that form stable hydrates or hemiacetals Click Here.