This limits the use of deuterium labeling at certain positions in protic solvents, for example.
3.
Note the gross increase in reaction rates when changing from a protic solvent to an aprotic solvent.
4.
Tosylates tend to form the alkene if the reaction is done in a protic solvent in basic conditions.
5.
The use of protic solvents results in the Bouveault-Blanc reduction of the separate esters rather than condensation.
6.
This difference arises from acid / base reactions between protic solvents ( not aprotic solvents ) and strong nucleophiles.
7.
Other features include reliability, predictability, selectivity, functional group tolerance and inertness to water and other protic solvents.
8.
Avobenzone is sensitive to the properties of the solvent, being relatively stable in polar protic solvents and unstable in nonpolar environments.
9.
In protic solvents, the equilibrium lies towards the keto form as the intramolecular hydrogen bond competes with hydrogen bonds originating from the solvent.
10.
This actually creates a problem in protic solvents, as they are typically very good at accepting hydrogen bonds if not outright reacting with the solvent.
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