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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: a confused chiral girl on December 03, 2006, 05:26:32 AM

Title: acetoacetate ester synthesis
Post by: a confused chiral girl on December 03, 2006, 05:26:32 AM
Which one of the following ketones can be made via an acetoacetate ester synthesis?
Title: Re: acetoacetate ester synthesis
Post by: Dan on December 03, 2006, 07:34:56 AM
at least attempt the question.
Title: Re: acetoacetate ester synthesis
Post by: a confused chiral girl on December 03, 2006, 02:53:50 PM
I have attempted the question, but didn't post what I did. Sorry  :'(  I know that the acetoacetic ester syn thessi yelds a methyl ketone by adding 3 carbons to the reactant. I am so confused in this question, because I tried to find one choice that has the most Carbons (since it's adding 3 carbons..then it must be long chain), but I don't know why the reactant is not given in this problem. So yes, what I did was trying to find the choice with the most Carbons, and I ended up wrong.  :-\ Sorry, I know that is not an acceptable way of attempting this question, but I really have no other choice to do this when they don't give me the reactant.
Title: Re: acetoacetate ester synthesis
Post by: Dan on December 03, 2006, 05:27:43 PM
I have attempted the question, but didn't post what I did. Sorry  :'(  I know that the acetoacetic ester syn thessi yelds a methyl ketone by adding 3 carbons to the reactant.

You don't necessarily have to add 3 carbons.
Have a read of this http://www.chem.ucalgary.ca/courses/351/Carey/Ch21/ch21-5-1.html
Title: Re: acetoacetate ester synthesis
Post by: a confused chiral girl on December 03, 2006, 10:10:32 PM
ok, I think #2 is the right answer. Please tell me if I am correct, please!! tanks!
Title: Re: acetoacetate ester synthesis
Post by: movies on December 04, 2006, 01:11:30 AM
I think that 2 would be pretty difficult to make by this sequence.  Think about the alkylating agent you would have to use.