Attack on Epoxide: What Did I Do Wrong?

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  • Thread starter Prabs3257
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In summary, the correct answer for the question is option D because no carbocation is formed in this reaction due to the SN2 mechanism. The carbon most susceptible to attack by the alkoxide is C3, as the highly strained 3-member oxirane makes oxygen a better leaving group than chlorine. Therefore, the option marked as the answer in the answer key is correct.
  • #1
Prabs3257
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Homework Statement
Reaction on epoxide
Relevant Equations
Electrophile attack
According to me the option that is marked should be the answer because the oEt- will attack the carbon on the epoxide which forms the stable carbocation but in the answer key the answer is given to be d please tell me what i did wrong
 

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  • #2
No carbocation formed, this is SN2.
 
  • #3
When an anion attacks, no carboCATION can be formed, right?
 
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  • #4
So this is probably going to scramble your noggin a bit... Number the carbons on the starting epoxide (epichlorohydrin) 1 thru 3 starting at the carbon attached to the chlorine.

Which carbon is most susceptible to attack by the alkoxide? C1? C3? Remember that the highly strained 3-member oxirane makes oxygen a much better leaving group than Cl-.
 

Related to Attack on Epoxide: What Did I Do Wrong?

1. What is an epoxide?

An epoxide is a type of organic compound that contains a three-membered ring consisting of two carbon atoms and one oxygen atom. It is commonly used in the production of plastics, adhesives, and solvents.

2. How does an epoxide attack occur?

An epoxide attack occurs when a nucleophile (a molecule that is attracted to positively charged atoms) attacks the carbon atom in the epoxide ring, causing the oxygen atom to break off and form a bond with the nucleophile. This results in the opening of the epoxide ring and the formation of a new compound.

3. What are the potential reasons for an unsuccessful epoxide attack?

There are several potential reasons for an unsuccessful epoxide attack, including incorrect reaction conditions, use of impure reagents, or the presence of inhibitors that prevent the reaction from occurring.

4. What are the possible side reactions that can occur during an epoxide attack?

During an epoxide attack, several side reactions can occur, such as ring opening of the epoxide to form a diol, rearrangement of the epoxide to form a different compound, or attack by a second nucleophile leading to a mixture of products.

5. How can I improve the success rate of an epoxide attack?

To improve the success rate of an epoxide attack, it is important to use pure reagents and carefully control the reaction conditions. Additionally, the use of catalysts or adjusting the reaction temperature can also help to promote a successful epoxide attack.

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