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Formation of Acetals under Acid Conditions

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This Demonstration considers the chemical kinetics of the formation of acetals from hemiacetals. This reaction, unlike the formation of hemiacetals [1], can only take place with acid catalysis. In fact, this reaction is a substitution reaction, replacing the –OH group with the –OR group, and an acid solution is necessary to transform –OH into , thus obtaining a good leaving group. If an ion is formed and an excess of charge is present, a colored shadow identifies the charge and its center: purple indicates an excess of positive charge, while green indicates an excess of negative charge.

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You can choose to focus on the functional groups.

The reaction summary help to schematize the overall reaction and the animated arrows show how electrons move in the reaction.

In (, framed means this acts only as catalyst, not being consumed nor produced). You can choose between one of the three stages of this reaction, which are:

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Contributed by: D. Meliga, V. Giambrone, L. Lavagnino and S. Z. Lavagnino Additional contribution by: F. Calcagno (I.T.I.S. Artom) (January 2024)
Open content licensed under CC BY-NC-SA

Snapshots

Details

Snapshot 1: first step of the acid catalysis, a proton transfer to start the reaction

Snapshot 2: second step of the acid catalysis, a water molecule loss to form the carbocation

Snapshot 3: third step of the acid catalysis, a nucleophile attack between the carbocation and the methanol

Snapshot 4: final step of the acid catalysis, a proton loss to produce the acetal

References: [1] Addizioni nucleofile ai chetoni https://www.youtube.com/watch?v=dKQLBPJ8Jew&list=PLswwssc6Q2ybl1IVEY56LVc16XsDKzFr-&index=48 [2] Hydrates, Hemiacetals, and Acetals https://www.masterorganicchemistry.com/2010/05/28/acetals-hemiacetals-hydrates/

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