Home >
Community >
What is the reaction mechanism of B-naphthol methyl ether via Williamson synthesis method with any strong base?
Upvote
13
Downvote
+ Chemical reactions
+ Chemical synthesis
+ Methods
+ Chemistry
+ Organic chemistry
+ Reaction mechanisms
+ Mechanisms
Posted by
Future Worlds
What is the reaction mechanism of B-naphthol methyl ether via Williamson synthesis method with any strong base?
The base deprotonates beta-naphthol to beta-naphthoxide, which then undergoes a Walden inversion (SN2) reaction with, for example, methyl bromide or iodide.
The base deprotonates beta-naphthol to beta-naphthoxide, which then undergoes a Walden inversion (SN2) reaction with, for example, methyl bromide or iodide.
It is a simple SN2 substitution reaction. Iodomethane undergoes backside attack by the naphthyloxide anion. (Naphthyloxide is formed by deprotonation of the OH in naphthol much like formation of phenoxide from phenol. Sodium hydroxide is a strong enough base to do this.)
It is a simple SN2 substitution reaction. Iodomethane undergoes backside attack by the naphthyloxide anion. (Naphthyloxide is formed by deprotonation of the OH in naphthol much like formation of phenoxide from phenol. Sodium hydroxide is a strong enough base to do this.)
The base deprotonates beta-naphthol to beta-naphthoxide, which then undergoes a Walden inversion (SN2) reaction with, for example, methyl bromide or iodide.
The base deprotonates beta-naphthol to beta-naphthoxide, which then undergoes a Walden inversion (SN2) reaction with, for example, methyl bromide or iodide.
More
VOTE
It is a simple SN2 substitution reaction. Iodomethane undergoes backside attack by the naphthyloxide anion.
(Naphthyloxide is formed by deprotonation of the OH in naphthol much like formation of phenoxide from phenol. Sodium hydroxide is a strong enough base to do this.)
It is a simple SN2 substitution reaction. Iodomethane undergoes backside attack by the naphthyloxide anion.
(Naphthyloxide is formed by deprotonation of the OH in naphthol much like formation of phenoxide from phenol. Sodium hydroxide is a strong enough base to do this.)
More
VOTE