Search results
Results from the WOW.Com Content Network
In organic chemistry, a hemiacetal is a functional group the general formula R 1 R 2 C(OH)OR, where R 1, R 2 is a hydrogen atom or an organic substituent. They generally result from the nucleophilic addition of an alcohol (a compound with at least one hydroxy group ) to an aldehyde ( R−CH=O ) or a ketone ( R 2 C=O ) under acidic conditions.
Acetals are stable compared to hemiacetals but their formation is a reversible equilibrium as with esters. As a reaction to create an acetal proceeds, water must be removed from the reaction mixture, for example, with a Dean–Stark apparatus , lest it hydrolyse the product back to the hemiacetal.
The latter reagent in itself is an acetal and therefore the reaction is actually a cross-acetalisation. Kinetic reaction control results from 2-methoxypropene as the reagent. D-ribose in itself is a hemiacetal and in equilibrium with the pyranose 3. In aqueous solution ribose is 75% pyranose and 25% furanose and a different acetal 4 is formed.
In contradistinction to the O,O‑acetal case, it is not needed to remove water from the reaction mixture in order to shift the equilibrium. [65] S,O-Acetals are hydrolyzed a factor of 10,000 times faster than the corresponding S,S-acetals. Their formation follows analogously from the thioalcohol.
It forms acetals readily, a prominent one being the spirocycle derived from pentaerythritol, diallylidene pentaerythritol. Acrolein participates in many Diels-Alder reactions , even with itself. Via Diels-Alder reactions, it is a precursor to some commercial fragrances, including myrac aldehyde ("lyral") and norbornene -2-carboxaldehyde. [ 5 ]
If reaction is between the C-4 hydroxyl and the aldehyde, a furanose is formed instead. [1] The pyranose form is thermodynamically more stable than the furanose form, which can be seen by the distribution of these two cyclic forms in solution. [2] Formation of pyranose hemiacetal and representations of β-D-glucopyranose
Hemithioacetal functional group. In organic chemistry, hemithioacetals (or thiohemiacetals) are organosulfur compounds with the general formula R−CH(−OH)−SR’.They are the sulfur analogues of the acetals, R−CH(−OH)−OR’, with an oxygen atom replaced by sulfur (as implied by the thio-prefix).
Main page; Contents; Current events; Random article; About Wikipedia; Contact us; Donate; Pages for logged out editors learn more