I am currently attempting to generate an arrow pushing mechanism for the oxidation of glucose to gluconic acid using Fehling's solution. My original thought was to go the route of alcohol oxidation using acidified dichromate where the alcohol attacks in and loses the H using a E2 mechanism.

In the aldehyde oxidation, I would have a hydroxide ion attack prior to the H bond collapse leaving an extra electron on the Cu from the $\ce{C-\mathbf{O-Cu}}$ bond resulting in reduction of $\ce{Cu^2+ -> Cu+}$. Which would satisfy the observed empirical data. After an attempt I googled the mechanism finding very little real information.

A post on this very site suggested the mechanism proceeds via enolate formation followed by single electron transfer with $\ce{Cu^2+}$. Unfortunately, there is no elaboration on this or a source, I also can't find a source online which corroborates this mechanism. Does anyone have a good source for this?

I am currently attempting to generate an arrow pushing mechanism for the oxidation of glucose to gluconic acid using Fehling's solution. My original thought was to go the route of alcohol oxidation using acidified dichromate where the alcohol attacks in and loses the H using a E2 mechanism.

In the aldehyde oxidation, I would have a hydroxide ion attack prior to the H bond collapse leaving an extra electron on the Cu from the $\ce{C-\mathbf{O-Cu}}$ bond resulting in reduction of $\ce{Cu^2+ -> Cu+}$. Which would satisfy the observed empirical data. After an attempt I googled the mechanism finding very little real information.

A post on this very site suggested the mechanism proceeds via enolate formation followed by single electron transfer with $\ce{Cu^2+}$. Unfortunately, there is no elaboration on this or a source, I also can't find a source online which corroborates this mechanism. Does anyone have a good source for this?

I am currently attempting to generate an arrow pushing mechanism for the oxidation of glucose to gluconic acid using Fehling's solution. My original thought was to go the route of alcohol oxidation using acidified dichromate where the alcohol attacks in and loses the H using a E2 mechanism.

In the aldehyde oxidation, I would have a hydroxide ion attack prior to the H bond collapse leaving an extra electron on the Cu from the C-O-Cu bond resulting in reduction of Cu2+ --> Cu1+. Which would satisfy the observed empirical data. After an attempt I googled the mechanism finding very little real information.

A post on this very site suggested the mechanism proceeds via enolate formation followed by single electron transfer with Cu2+. Unfortunately, there is no elaboration on this or a source, I also can't find a source online which corroborates this mechanism. Does anyone have a good source for this?

I am currently attempting to generate an arrow pushing mechanism for the oxidation of glucose to gluconic acid using Fehling's solution. My original thought was to go the route of alcohol oxidation using acidified dichromate where the alcohol attacks in and loses the H using a E2 mechanism.

In the aldehyde oxidation, I would have a hydroxide ion attack prior to the H bond collapse leaving an extra electron on the Cu from the $\ce{C-\mathbf{O-Cu}}$ bond resulting in reduction of $\ce{Cu^2+ -> Cu+}$. Which would satisfy the observed empirical data. After an attempt I googled the mechanism finding very little real information.

A post on this very site suggested the mechanism proceeds via enolate formation followed by single electron transfer with $\ce{Cu^2+}$. Unfortunately, there is no elaboration on this or a source, I also can't find a source online which corroborates this mechanism. Does anyone have a good source for this?