Sunday, July 18, 2010

Organic chem problem?

Draw the skeletal structure of the major organic product A which is the compound of interest. (There is another product that can be considered the by-product which is of no synthetic interest.)

There is one equivalent of base used.

http://www.webassign.net/userimages/kasandbe@ncsu/CH223_fall_02/223fall02_HW27ae.gif
This reaction is a crossed or mixed Claisen condensation. This is not within my preferred types of examples. See examples here:

http://www2.chemistry.msu.edu:80/faculty



However, acetone is the more acidic component and will enolize most readily. If its concentration is kept low to discourage self-condensation, then that enolate can react with the ester to give a diketone after elimination of methoxide. Because of the diketone acidity, the methoxide will deprotonate the diketone. This will be the first product. Acidification is required to convert the enolate back to the diketone, 5-methylhexane-2,4-dione.



Acetone is quite reactive and susceptible to self-condensation. If you look at the examples shown in the linked web page, you will find that esters used with ketones are often quite reactive, such as ethyl formate.

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