There are two important functional groups in organic chemistry interconnected in many ways; they are aldehyde and ketone. An ‘R’ group and a hydrogen atom are bonded to a carbonyl group (CO) to compose an aldehyde. On the other hand, ketones contain two ‘R’ groups bound to a carbonyl group. The acid catalysts are acids that speed up the reaction rate as catalysts are never eaten alive in a chemical reaction. Their role is to ensure the reaction reaches completion in record reaction time. The formation of acetals or geminal-diether derivatives from aldehydes or ketones occurs by reaction with two equivalents or an excess amount of alcohol and water removal. The ketone derivatives of such type of reaction were once called ketals, but nowadays, this term’s usage has dropped. A hemiacetal is formed as an intermediate during the reaction of formation of an acetal.
Mechanism of Acetal Formation:
The mechanism of acetal formation comprises two main steps. The first step initiates with the protonation of the carbonyl group that makes it more electrophilic. As a nucleophile, the first alcohol molecule attacks the protonated carbonyl and produce an oxonium ion intermediate. Later, an acid deprotonates this intermediate of oxonium ion to give a hemiacetal. Step two involves the transformation of hemiacetal to acetal with a similar mechanism of step one. It initiates with the hydroxide group protonation by an acid that releases water as a leaving group. Such water removal redevelops the double bond of carbon and oxygen, which makes it more electrophilic for the nucleophile attack. The addition of a second molecule of alcohol with hemiacetal takes place, which produces another oxonium ion as an intermediate.
Further, deprotonation of the as-obtained intermediate is done by an acid catalyst to gives out an acetal. Each step in the reaction process is reversible and administered by equilibrium. The equilibrium can be shifted in either direction for ketones in the left or right for aldehydes. Hence, acetals formation is favored by employing excess alcohol or water removal and formation of aldehydes or ketones favored by water addition. Using aqueous acid by the hydrolysis process, they get hydrolyzed. Generally, acetals are stable under neutral and basic conditions, and by neutralizing with the acid, the catalyst can be isolated as a pure substance. The acetals can also be employed during synthesis for protecting and masking the carbonyl group into an ether-like moiety, i.e. comparatively unreactive. The carbonyl groups are protected from nucleophilic attack by the cyclic acetal formation.
Acetals Functions like Protecting Groups:
In strongly basic and neutral conditions, acetals are less reactive and highly stable, which acquires their great importance as carbonyl derivatives. Generally, they reduce reactivity related to ethers exhibited by acetals as long as acids, particularly aqueous acids do not treat them. The reactivity of aldehydes and ketones toward strongly nucleophilic metallo-hydride, alkyl, and aryl reagents is among their most useful and characteristic reactions. These powerful reagents will not affect the carbonyl group after conversion into an acetal and prevent irreversible addition reactions. Hence, acetals are excellent protective groups.
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