Home >
Community >
Can benzyl bromide be directly oxidized to benzoic acid?
Upvote
12
Downvote
+ Biochemistry
+ Acids
+ Chemistry
+ Oxides
+ Organic chemistry
Posted by
Akinlade Akinlolu
Can benzyl bromide be directly oxidized to benzoic acid?
I thin Edward Brown is more or less correct but just needs to be bolder.
Toluene is readily oxidized to benzoic acid with KMnO4, in water/heat followed by an acidic workup.
I am pretty certain that similar treatment of benzyl bromide will lead to benzoic acid with the intermediate formation of benzoyl iodide. Such will be readily hydrolyzed by the aqueous conditions the oxidation is conducted in.
I thin Edward Brown is more or less correct but just needs to be bolder.
Toluene is readily oxidized to benzoic acid with KMnO4, in water/heat followed by an acidic workup.
I am pretty certain that similar treatment of benzyl bromide will lead to benzoic acid with the intermediate formation of benzoyl iodide. Such will be readily hydrolyzed by the aqueous conditions the oxidation is conducted in.
My answer will depend upon what you mean by “directly”. Does that mean in exactly one step? Or does that mean in the same reaction flask with multiple steps?
It would seem likely and possible to oxidize benzyl bromide using permanganate in aqueous base to benzoate. But there would probably be several steps in that mechanism including some hydrolysis steps of various intermediates in the reaction flask. Would that still count as “directly” to you?
Furthermore, benzoate ion would be created in this reaction; is not benzoic acid. It is the anionic salt of benzoic acid. So, one would need an acidification step to create the benzoic acid from benzoate ion. That is a second step; does that still count as “directly” to you?
My answer will depend upon what you mean by “directly”. Does that mean in exactly one step? Or does that mean in the same reaction flask with multiple steps?
It would seem likely and possible to oxidize benzyl bromide using permanganate in aqueous base to benzoate. But there would probably be several steps in that mechanism including some hydrolysis steps of various intermediates in the reaction flask. Would that still count as “directly” to you?
Furthermore, benzoate ion would be created in this reaction; is not benzoic acid. It is the anionic salt of benzoic acid. So, one would need an acidification step to create the benzoic acid from benzoate ion. That is a second step; does that still count as “directly” to you?
I thin Edward Brown is more or less correct but just needs to be bolder.
Toluene is readily oxidized to benzoic acid with KMnO4, in water/heat followed by an acidic workup.
I am pretty certain that similar treatment of benzyl bromide will lead to benzoic acid with the intermediate formation of benzoyl iodide. Such will be readily hydrolyzed by the aqueous conditions the oxidation is conducted in.
I thin Edward Brown is more or less correct but just needs to be bolder.
Toluene is readily oxidized to benzoic acid with KMnO4, in water/heat followed by an acidic workup.
I am pretty certain that similar treatment of benzyl bromide will lead to benzoic acid with the intermediate formation of benzoyl iodide. Such will be readily hydrolyzed by the aqueous conditions the oxidation is conducted in.
More
VOTE
My answer will depend upon what you mean by “directly”. Does that mean in exactly one step? Or does that mean in the same reaction flask with multiple steps?
It would seem likely and possible to oxidize benzyl bromide using permanganate in aqueous base to benzoate. But there would probably be several steps in that mechanism including some hydrolysis steps of various intermediates in the reaction flask. Would that still count as “directly” to you?
Furthermore, benzoate ion would be created in this reaction; is not benzoic acid. It is the anionic salt of benzoic acid. So, one would need an acidification step to create the benzoic acid from benzoate ion. That is a second step; does that still count as “directly” to you?
My answer will depend upon what you mean by “directly”. Does that mean in exactly one step? Or does that mean in the same reaction flask with multiple steps?
It would seem likely and possible to oxidize benzyl bromide using permanganate in aqueous base to benzoate. But there would probably be several steps in that mechanism including some hydrolysis steps of various intermediates in the reaction flask. Would that still count as “directly” to you?
Furthermore, benzoate ion would be created in this reaction; is not benzoic acid. It is the anionic salt of benzoic acid. So, one would need an acidification step to create the benzoic acid from benzoate ion. That is a second step; does that still count as “directly” to you?
More
VOTE