Organic Chemistry Reaction of Carbonyl compound

In summary, the conversation discusses the attempt to figure out a reaction mechanism involving the addition of an alcohol to a carbonyl compound and the subsequent intramolecular bonding. The idea of protonating every oxygen on the starting compound is suggested, leading to the formation of an acetal and further hydrolysis to yield the desired product, ethanal. The individual seeking help confirms this solution and expresses gratitude for the assistance.
  • #1
Galgenstrick
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Homework Statement


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Homework Equations


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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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  • #2
What else can the acid do to your starting molecule? Does the carbon singly bonded to two oxygens remind you of anything?
 
  • #3
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?
 
  • #4
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?
 
  • #5
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.
 

FAQ: Organic Chemistry Reaction of Carbonyl compound

What is a carbonyl compound?

A carbonyl compound is an organic compound that contains a carbon atom double-bonded to an oxygen atom, also known as a carbonyl group. Examples of carbonyl compounds include aldehydes, ketones, carboxylic acids, and esters.

How do carbonyl compounds react in organic chemistry?

Carbonyl compounds are highly reactive and participate in a variety of chemical reactions, including nucleophilic addition, nucleophilic substitution, and condensation reactions. These reactions are important for the synthesis of various organic compounds.

What is the difference between an aldehyde and a ketone?

Both aldehydes and ketones contain a carbonyl group, but in aldehydes, the carbonyl group is located at the end of a carbon chain, whereas in ketones, it is located within the carbon chain. This structural difference affects their reactivity and properties.

How does the structure of a carbonyl compound affect its reactivity?

The reactivity of a carbonyl compound is influenced by the presence of electron-withdrawing or electron-donating groups attached to the carbonyl group. Electron-withdrawing groups increase the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack. Electron-donating groups decrease the electrophilicity of the carbonyl carbon, making it less reactive.

What are some common applications of carbonyl compounds in everyday life?

Carbonyl compounds have many practical applications, including being used as solvents, preservatives, flavorings, and fragrances. They are also important intermediates in the production of pharmaceuticals, plastics, and other industrial products.

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