Reaction of acetaldehyde with formaldehyde?
Good Midnight In The Midnight,
Task:
" Draw the reaction products and state the name and/or class of substance. Take into account the occurrence of stereoisomers, if applicable."
Solution:
Problem:
I don't quite understand the solution. I know that the one on the left is acetaldehyde and the one on the right is formaldehyde. Now there's a negative charge on the left because there's nothing attached to it. So we have a nucleophile here. The nucleophile is now attached to the point marked in red because there's a positive charge there, as the oxygen atom attracts the electrons from the carbon. That's not right.
Now I need to attach the nucleophile to the red dot. It looks like this:
So, now we have the problem that the carbon above has five bonds. I would have removed one of the two H bonds, but our professor now moves the upper double bond of the oxygen atom one upward. I don't quite understand this. Wouldn't it be easier to simply remove one H and split it off somehow? Also, in the solution on the right, there's suddenly an OH. How did the H get there? Did he simply move the double bond of the oxygen upward so that there's a free electron pair, and then, as if by magic, fit one of the H atoms in there. So, like this:
=>
But then there would be one H too many.
I'm sorry, but I really don't understand how exactly the substitution was carried out here. The aldehyde is attached to the carbon atom of the formaldehyde. But how one arrives at the solution is a mystery to me.
LG, Jensek81
The principle of aldol addition and as a result of the condensation is the following. In the first step, the acidic alpha-C of a carbonyl compound acts on the carbonyl-C of a further carbonyl compound, or also on a molecule of the same type. In the present case, there is only one compound with an alpha-C, the acetaldehyde. Formally, the mechanism can be formulated by abstracting a proton from the alpha-C from the acetaldehyde. The carbanion acts with the free electron on the carbonyl-C of formaldehyde, wherein a binding electron is pushed onto the oxygen of formaldehyde, which thereby receives a negative charge. It now acts as a proton and exactly the compound shown in the representation of the solution is obtained, 3-hydroxypropanal. It should be noted that the nucleophilic attack of the carbanion on the planar geometry of the acetaldehyde can take place from two sides (from “top” or “bottom”) with the same probability. A racemic addition product is thereby obtained.
See for the mechanism under aldol addition.