Which Product Won't Be Obtained in a Wurtz Reaction?

In summary, the conversation discusses the products obtained in a Wurtz reaction and specifically focuses on the possibility of obtaining an allyl radical. The participants discuss the factors that may influence the formation of this product and share resources for understanding its stability. The correct answer to the question is determined to be (d).
  • #1
baldbrain
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21

Homework Statement


Which one of the following products will not be obtained in the given Wurtz reaction?
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The Attempt at a Solution


Well, (a) will definitely be the major product. We know that this reaction may proceed by a free radical or an ionic mechanism. But what's that got to do with the C-14 shifting position inside the ring? Any help?
 

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  • #2
It might help to draw out the resonance structures of the radical/ionic intermediate.
 
  • #3
TeethWhitener said:
It might help to draw out the resonance structures of the radical/ionic intermediate.
Well, won't that conversion require additional energy? Do we presume it is available?
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  • #4
baldbrain said:
Well, won't that conversion require additional energy?
Why? Maybe draw the hydrogens explicitly.
 
  • #5
TeethWhitener said:
Why? Maybe draw the hydrogens explicitly.
What difference does that make? Won't THIS ##\downarrow## require additional energy?
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  • #6
baldbrain said:
Won't THIS ↓↓\downarrow require additional energy?
Google "allyl radical."
 
  • #7
TeethWhitener said:
Google "allyl radical."
****, you're right...I keep forgetting that.
 
  • #9
I don't know why, but I still don't have a keen eye spotting the allyl radical. Get me?
 
  • #10
You might remember I stumbled upon this 'allyl' thingy even in that "same SN1 & SN2 product" problem.
Anyway, Thanks again.:smile:
 
  • #11
baldbrain said:
I don't know why, but I still don't have a keen eye spotting the allyl radical.
It's not a bad idea to have the possibility of allylic resonance in the back of your mind whenever you see a double bond. Other than that, I'm not sure there are any tricks to remembering it.
 
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  • #12
I forgot to mention that the answer would be (d). You might've already guessed that.
 
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1. What is a Wurtz reaction?

A Wurtz reaction is a type of chemical reaction in which two alkyl halides are combined to form a carbon-carbon bond, typically in the presence of a strong base like sodium or potassium.

2. Why is it important to know which product won't be obtained in a Wurtz reaction?

Knowing which product won't be obtained in a Wurtz reaction is important because it can help guide scientists in designing and predicting the outcome of a chemical reaction. It can also help determine the most efficient and effective way to synthesize a desired compound.

3. What determines which product is obtained in a Wurtz reaction?

The product obtained in a Wurtz reaction is determined by the type of alkyl halides used, the strength of the base, and the reaction conditions such as temperature and solvent. These factors influence the formation of different products, such as primary, secondary, or tertiary alkanes.

4. Can any alkyl halide be used in a Wurtz reaction?

No, not all alkyl halides can be used in a Wurtz reaction. The alkyl halide must be able to form a stable carbocation in order for the reaction to occur. Alkyl halides with primary or secondary carbons are typically more reactive and therefore more suitable for a Wurtz reaction.

5. Are there any limitations to the Wurtz reaction?

Yes, there are limitations to the Wurtz reaction. It is not suitable for the synthesis of complex or highly functionalized molecules, as it can result in multiple products. Additionally, the use of strong bases can lead to unwanted side reactions or the formation of unwanted byproducts.

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