What is the Major Product of This Ester Reaction with Sulfuric Acid?

In summary, the conversation is about someone seeking help on a question regarding the major product of a reaction involving a cis olefin and different steps including the use of 1% aq H2SO4, isolation, and PCC/dichloromethane. The person had no idea how the reaction occurred and guessed the final product was an aldehyde. The correct answer is that the H2SO4 + boil will hydrolyze the ester into ethanoic acid and the alcohol 3 hydroxy cyclo octene, with the alcohol(s) being secondary. The question also asked what happens to a cis olefin upon treatment with hot, dilute acid.
  • #1
lat3ralus65
4
0
OK, so I just got out of an organic chemistry exam. I feel pretty good about every question except one which I did not know - please help me put my mind at ease!

What is the major product of the reaction of this molecule:

http://img216.imageshack.us/my.php?image=stupidthingdw3.jpg

with the following steps:

1.) 1% aq H2SO4, boil
2.) isolate product
3.) PCC/dichloromethane

I had no idea how the reaction occurred. I guessed that the final product was an aldehyde (methanal?) because I know PCC reacts with alcohols to form aldehydes/ketones (and that's all I knew).

What is it?
 
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  • #2
the H2SO4 + boil will hydrolyse the ester into ethanoic acid and the alcohol 3 hydroxy cyclo octene.

i just corrected this post. i made a mistake, the alcohol is secondary
 
Last edited:
  • #3
What happens to a cis olefin upon treatment with hot, dilute acid? The alcohol(s) are secondary.
 

FAQ: What is the Major Product of This Ester Reaction with Sulfuric Acid?

What is the purpose of the ester reaction with sulfuric acid?

The ester reaction with sulfuric acid is a chemical reaction that is commonly used in organic chemistry to form esters. Esters are compounds that are commonly found in natural fats and oils, and they are also responsible for the unique smells and flavors of many fruits and flowers. The reaction with sulfuric acid allows for the synthesis of new ester compounds, which can have a variety of industrial and commercial uses.

How does sulfuric acid act as a catalyst in the ester reaction?

Sulfuric acid acts as a catalyst in the ester reaction by protonating the carbonyl group of the ester, making it more reactive. This protonation also makes the carbonyl group more electrophilic, allowing it to react with a nucleophile (such as an alcohol or carboxylic acid) to form the ester. Additionally, sulfuric acid can also act as a dehydrating agent, removing water from the reaction mixture and driving the reaction forward.

Can other acids be used instead of sulfuric acid in the ester reaction?

Yes, other acids such as hydrochloric acid, phosphoric acid, and acetic acid can also be used in the ester reaction. However, sulfuric acid is often preferred due to its high acidity and strong dehydrating properties, which can lead to higher yields of the desired ester product. Additionally, sulfuric acid is relatively inexpensive and readily available, making it a popular choice for this reaction.

Is the ester reaction with sulfuric acid reversible?

Yes, the ester reaction with sulfuric acid is reversible. This means that the ester product can be converted back into the starting materials (an alcohol and a carboxylic acid) under certain conditions. This is known as ester hydrolysis, and it can occur in the presence of water and a strong acid or base. Therefore, it is important to carefully control the reaction conditions to ensure a high yield of the desired ester product.

Are there any safety precautions to take when working with sulfuric acid in the ester reaction?

Yes, there are several safety precautions that should be taken when working with sulfuric acid in the ester reaction. Sulfuric acid is a strong acid and can cause severe burns if it comes into contact with the skin or eyes. It is important to wear appropriate protective gear, such as gloves and goggles, and to handle the acid with care. Additionally, the reaction should be carried out in a well-ventilated area, as sulfuric acid can release toxic fumes. Proper disposal methods should also be followed to prevent environmental contamination.

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