[omegasynthesis999]

A synthetic equivalent is supposed to be a reagent whose structure, when in the final product, gives the appearance of having come from another starting reagent when as a starting material it had a different structural origin.

I believe an example is the ethyl acetoacetate ion and acetone enolate.

However I don't really understand why the two would be called synthetic equivalents. Doesn't the acetoacetate have the extra ester group attached to it in the final product?

Thanks

[omegasynthesis999]

Lets say I have the ethyl acetoacetate ion and do an Sn2 substitution with CH3Br. I then follow that up by converting the ester portion of the molecule to a carboxylic acid and then subsequently decarboxylate to get a 2-butanone.

Suppose I take the acetone enolate and then alkylate w/ CH3Br. I get the same 2-butanone.

Now would you call the two reagents synthetic equivalents because of the 2-butanone product or because they both undergo Sn2 rxns to yield similar looking products except the ethyl acetoacetate ion forms a more substituted product (prior to decarboxylation)?

[Dan]

Now would you call the two reagents synthetic equivalents because of the 2-butanone product or because they both undergo Sn2 rxns to yield similar looking products except the ethyl acetoacetate ion forms a more substituted product (prior to decarboxylation)?

The fact that you get the same product is the reason for the term synthetic equivalent.

[omegasynthesis999]

Thanks