Acetoacetic Ester Enolates Practice Problems
Practice
Determine the major product for each acetoacetic ester synthesis shown below:
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How would you use the acetoacetic ester synthesis to prepare each of the following products?
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This content is for registered users only.
By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.
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By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.
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hello Professor: I would like your opinion as to an alternate synthesis I have for your challenge problem above. I started as you did by producing the enolate ion and then adding a methyl group. From there I added 3-bromo-1-propanol, oxidized the OH group to an aldehyde, and then ran an Aldol using ethoxide using the methyl group on the keto portion of the AAE (acetoacetic ester). I hydrolyzed the ester, and then heated removing the carboxylate group and dehydrating the beta-hydroxy ketone I formed yielding the product.
I would like to know if my concepts are clear even if there is a mistake somewhere in the synthetic route.
Thanks for your time. A great web-site!
Hello,
Sounds like a feasible plan where only the decarboxylation step is done later. You can go ahead and email me (gevorg at chemistrysteps.com) your synthesis scheme so we can double-check.