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Dependence of primary alcohol oxidation on presence of water and strong or weak oxidants
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Afranio Torres-Filho
Dependence of primary alcohol oxidation on presence of water and strong or weak oxidants
After looking up more information and taking the comments of user55119 into account, I've decided to post an answer myself, hoping to clearly address the main question points.
The determinant factor of the products obtained from an oxidation reaction of primary alcohols is the presence of water in the reaction medium, as it allows the formation of an aldehyde hydrate which can be further oxidized. Thus, the distinction between "weak" and "strong" oxidants is not necessarily informative (and could even be misleading) and emphasis should be placed in the reaction mechanism alongside the reaction medium.
The oxidation of primary alcohols with Cr(VI) reagents takes place through the mechanism depicted in the question or slight variations of it (depending on the reagent chosen). Carboxylic acids are obtained only through an aldehyde intermediate.
After looking up more information and taking the comments of user55119 into account, I've decided to post an answer myself, hoping to clearly address the main question points.
The determinant factor of the products obtained from an oxidation reaction of primary alcohols is the presence of water in the reaction medium, as it allows the formation of an aldehyde hydrate which can be further oxidized. Thus, the distinction between "weak" and "strong" oxidants is not necessarily informative (and could even be misleading) and emphasis should be placed in the reaction mechanism alongside the reaction medium.
The oxidation of primary alcohols with Cr(VI) reagents takes place through the mechanism depicted in the question or slight variations of it (depending on the reagent chosen). Carboxylic acids are obtained only through an aldehyde intermediate.
After looking up more information and taking the comments of user55119 into account, I've decided to post an answer myself, hoping to clearly address the main question points.
The determinant factor of the products obtained from an oxidation reaction of primary alcohols is the presence of water in the reaction medium, as it allows the formation of an aldehyde hydrate which can be further oxidized. Thus, the distinction between "weak" and "strong" oxidants is not necessarily informative (and could even be misleading) and emphasis should be placed in the reaction mechanism alongside the reaction medium.
The oxidation of primary alcohols with Cr(VI) reagents takes place through the mechanism depicted in the question or slight variations of it (depending on the reagent chosen). Carboxylic acids are obtained only through an aldehyde intermediate.
Further reading:
McMurry, John. Organic Chemistry. 8th edition.
MasterOrganicChemistry
After looking up more information and taking the comments of user55119 into account, I've decided to post an answer myself, hoping to clearly address the main question points.
The determinant factor of the products obtained from an oxidation reaction of primary alcohols is the presence of water in the reaction medium, as it allows the formation of an aldehyde hydrate which can be further oxidized. Thus, the distinction between "weak" and "strong" oxidants is not necessarily informative (and could even be misleading) and emphasis should be placed in the reaction mechanism alongside the reaction medium.
The oxidation of primary alcohols with Cr(VI) reagents takes place through the mechanism depicted in the question or slight variations of it (depending on the reagent chosen). Carboxylic acids are obtained only through an aldehyde intermediate.
Further reading:
McMurry, John. Organic Chemistry. 8th edition.
MasterOrganicChemistry
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