Organic Chemistry Reaction of Carbonyl compound

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Discussion Overview

The discussion revolves around the reaction mechanisms involving carbonyl compounds, specifically focusing on the nucleophilic addition of alcohols to carbonyls and the role of acids in these reactions. Participants explore the hydrolysis of acetals and the resulting products.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation

Main Points Raised

  • One participant describes an attempt to reverse-engineer the mechanism involving nucleophilic addition of alcohol to the carbonyl carbon of ethanal, questioning if there is a simpler method.
  • Another participant inquires about the potential actions of acid on the starting molecule, hinting at structural similarities to acetals.
  • A participant asserts that the acid will protonate all oxygens in the starting compound and reflects on the structural implications of a carbon bonded to two oxygens, suggesting a connection to acetals.
  • There is a repeated mention of hydrolysis of the acetal leading to acetaldehyde (ethanal) and a request for clarification on the additional products formed.
  • One participant expresses gratitude for assistance, indicating they successfully resolved their homework problem, though the specifics of their solution are not detailed.

Areas of Agreement / Disagreement

Participants appear to engage in a collaborative exploration of the reaction mechanisms, with some agreement on the steps involved, particularly regarding the role of acid and hydrolysis. However, uncertainty remains about the exact structures of the products and whether the proposed approaches are correct.

Contextual Notes

There are unresolved aspects regarding the specific products formed from the reactions discussed, and assumptions about the mechanisms may vary among participants.

Who May Find This Useful

Students studying organic chemistry, particularly those focusing on reaction mechanisms involving carbonyl compounds and acetals.

Galgenstrick
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Homework Statement


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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!
 
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What else can the acid do to your starting molecule? Does the carbon singly bonded to two oxygens remind you of anything?
 
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?
 
Galgenstrick said:
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?
 
sjb-2812 said:
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.
 

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