Claisen Rearrangement for this molecule

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In summary, the new poster forgot to add a double bond to a molecule and the mechanism they used went through a 5-bonds-to-carbon intermediate or final product.
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di50rder
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Hey all,

I'm new here, but used to frequent in high school when I was having a lot of trouble with Physics. Now I'm taking O Chem and figured this could be a great resource to use again.

I had this question on a quiz today, just wondering if I did the Claisen rearrangement for this particular molecule correctly.

Thanks!

EDIT: Looks like you will have to click the thumbnail, then click the preview window that pops up to be able to view it normally. Sorry, drew it up in ChemDraw and exported as a gif, wasn't sure what file type would work best. Thanks to anyone who can help!

EDIT 2: If anyone could move this to the Homework forum that would be great...figure it probably belongs there rather than here. Don't want to double post. Thanks!
 

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di50rder said:
Hey all,

I'm new here, but used to frequent in high school when I was having a lot of trouble with Physics. Now I'm taking O Chem and figured this could be a great resource to use again.

I had this question on a quiz today, just wondering if I did the Claisen rearrangement for this particular molecule correctly.

Thanks!

EDIT: Looks like you will have to click the thumbnail, then click the preview window that pops up to be able to view it normally. Sorry, drew it up in ChemDraw and exported as a gif, wasn't sure what file type would work best. Thanks to anyone who can help!

EDIT 2: If anyone could move this to the Homework forum that would be great...figure it probably belongs there rather than here. Don't want to double post. Thanks!

Can't see what you did there but it looks to me like you forgot a double bond and your mechanism goes through a 5-bonds-to-carbon intermediate or final product. That's bad ju-ju any way you look at it.
 

What is the Claisen Rearrangement?

The Claisen Rearrangement is a chemical reaction in which an allyl or benzyl vinyl ether is converted into a different type of vinyl ether through a series of steps involving rearrangement of the molecule's bonds.

How does the Claisen Rearrangement work?

The Claisen Rearrangement involves the formation of a reactive intermediate known as a vinyl carbanion, which then undergoes rearrangement through the migration of an alkyl or aryl group to a different position on the molecule. This results in the formation of a new vinyl ether with a different structure.

What are the applications of the Claisen Rearrangement?

The Claisen Rearrangement is commonly used in organic synthesis to create new carbon-carbon bonds and to introduce functional groups into molecules. It is also useful in the preparation of natural products, pharmaceuticals, and other complex organic compounds.

What factors influence the rate of the Claisen Rearrangement?

The rate of the Claisen Rearrangement is influenced by several factors, including the nature of the substituents on the allyl or benzyl vinyl ether, the strength of the base used to initiate the reaction, and the solvent used. Steric hindrance and electronic effects can also have a significant impact on the rate of the reaction.

Are there any limitations or drawbacks to the Claisen Rearrangement?

Like any chemical reaction, the Claisen Rearrangement has limitations and drawbacks. One major limitation is that it only works on allyl or benzyl vinyl ethers, which restricts the types of molecules that can undergo this transformation. In addition, the reaction may also produce unwanted byproducts or require harsh reaction conditions, making it challenging to control. Careful consideration of these factors is necessary when using the Claisen Rearrangement in a synthesis.

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