Resources for percent yield of haloform reactions

Resources for predicted percent yields of reactions are often found in published papers. Here is a link to a paper that uses the synthesis technique you used:

http://jade6.truman.edu/~patter/organic/procedures/multistep.pdf

On page 2, you can find this quote:

"Less frequently, it is used in the undergraduate chemistry curriculum to demonstrate formation of a carboxylic acid by oxidizing a methyl ketone. In this published experiment, acetophenone, under basic conditions, is oxidized with
household bleach (sodium hypochlorite) to form benzoic acid and chloroform [4, 5]."

This article cites two more articles (4 and 5). At the end of the article, full citations are given:

[4] Perkins, R. R.; Chau, F. J. Chem. Ed., 1982, 59, 981.
[5] Perkins, R. R. J. Chem. Ed., 1984, 61, 514.

Both of these citations come from the Journal of Chemical Eductation and should give a percent yield for your reaction. Without purchasing a subscription, you could go to your school's library which should probably give you access to these journals.

As for the amount of mixing affecting percent yield, you need to consider that acetophenone is only slightly soluble in water. Because the bleach solution is aqueous, the acetophenone will not readily mix with the bleach. If the reaction vessel was not mixed well, the bleach would not have an opportunity to mix (and react) with the acetophenone and would result in a low percent yield.

This content was COPIED from BrainMass.com - View the original, and get the already-completed solution here!