(20 pts] Provide the detailed mechanism of hydration of the following aldehyde in acidic solution. (You need to show all steps, reagents,
bonds, atoms, lone pairs, charges and arrows that are involved and required for the mechanism reactions)
Н.
The equilibrium for hydrate formation depends both on steric and electrical factors of the carbonyl as discussed in the previous section. In most cases the resulting gem-diol is unstable relative to the reactants and cannot be isolated. Exceptions to this rule exist, one being formaldehyde where the small size of the hydrogen substituents relative to aldehydes and ketones favor hydrate formation. Thus, a solution of formaldehyde in water (formalin) is almost exclusively the hydrate, or polymers of the hydrate. The addition of electron donating alkyl groups stabilized the partial positive charge on the carbonyl carbon and decreases the amount of gem-diol product at equilibrium. Because of this ketones tend to form less than 1% of the hydrate at equilibrium.
