Organic Chemistry Reaction of Carbonyl compound

[Galgenstrick]

Homework Statement

Homework Equations

N/A

The Attempt at a Solution

I attempted to figure out the mechanism in reverse. I have tried neucleophilic addition of the alcohol to the carbonyl carbon of the ethanal, followed by the addition of the resulting hydroxyl group (from the tetrahedral intermediate) bonding intramolecularly to the carbonyl carbon of the ester. There must be a simpler way?

Please help!

 

[sjb-2812]

What else can the acid do to your starting molecule? Does the carbon singly bonded to two oxygens remind you of anything?

 

[Galgenstrick]

The acid will protonate every oxygen on the starting compound. The only thing that the carbon single bonded to the two oxygens reminds me of is an acetel. I tried that also, and I wasn't able to come up with the structures of the products from that reaction. Is this the right track and I possibly made a mistake?

 

[sjb-2812]

The acid will protonate every oxygen on the starting compound. The only thing that the carbon single bonded to the two oxygens reminds me of is an acetel. I tried that also, and I wasn't able to come up with the structures of the products from that reaction. Is this the right track and I possibly made a mistake?

I believe that you're right, the first step would be hydrolysis of the acetal, yielding the acetaldehyde (ethanal) product and what else?

 

[Galgenstrick]

I believe that you're right, the first step would be hydrolysis of the acetal, yielding the acetaldehyde (ethanal) product and what else?

Sorry it took so long to reply. You have helped a lot! I ended up getting this 100% correct! Thank you.