The mechanism of acid-catalyzed hydrolysis of acetals to aldehydes and ketones. This is the reversed reaction between carbonyls and alcohols.

What happens to 1,5-dimethyl-6,8-dioxabicyclo [3.2.1]octane when it is hydrolyzed under acidic conditions? I know that under acidic conditions the first thing to likely happen is protonation. Does it matter which oxygen is protonated first? Once that oxygen has been protonated it is going to want to return to neutrality.

2010年5月28日 · Hydrates, hemiacetals and acetals are the products of addition reactions of oxygen-based nucleophiles (water and alcohols) to aldehydes and ketones. A hydrate contains a carbon with two single bonds to OH. An acetal (sometimes called a ketal if originating from a ketone) contains a carbon with two single bonds to OR groups.

Mechanistically speaking, the acetal hydrolysis is a combination of all the same proton transfer, nucleophilic attack, and leaving group dissociation steps as in the acetal formation, but in reverse. And here’s another example of a cyclic acetal hydrolysis:

2000年5月26日 · A better understanding of the hydrolytic behaviour of acyclic and cyclic acetals, ketals, orthoesters and orthocarbonates is important for mechanistic reasons 1 and can be useful in organic synthesis either for the design of stereocontrolled processes or for the selection of appropriate hydroxyl and carbonyl protecting groups. 2 We wish to ...

Facile Synthesis and Photo-Tunable Properties of a Photosensitive Polymer Whose Chromophores Bound with pH-Labile Cyclic Acetal Linkages. Macromolecules 2008 , 41 (13) , 4597-4606.

hydrolysis of cyclic acetals or ketals, the principle of microscopic reversibility [16] requires that the ring closure 9a, b → 10 (Fig. 6.2) be the rate-determining step for the formation of cyclic acetals or ketals.

1997年10月20日 · A series of cyclic and acyclic acetals and ketals were hydrolyzed to their corresponding carbonyl compounds by a catalytic amount of CBr 4 (20%) in CH 3 CN/H 2 O solvent mixture under different energy sources, thermal or ultrasound. The highly chemoselective hydrolysis can be achieved under ultrasonic reaction condition.

2024年1月16日 · Cyclic acetals are more stable towards hydrolysis than acyclic ones and are also kinetically favored because the intramolecular ring-closing reaction is fast. Once the addition reaction is accomplished (or whatever reaction required protecting the carbonyl), the reversibility of acetal formation can be used to reform the original carbonyl.

1979年7月1日 · We now describe an improved method employing differential hydrolysis of cyclic acetals. It is well known that the rate of hydrolysis of benzylidene and substituted benzylidene groups can be strongly influenced by substituents on the aromatic ring.