This is the blog for Kimberly Petersen's Organic Chemistry II CHE 352-01 class at the University of North Carolina at Greensboro. The blog is an opportunity for students to share questions/thoughts/musings on organic chemistry.
Tuesday, March 26, 2013
question about the notes 3/25
Hey guys,
I must not have written it down....but why does the acid anhydride (when reacted with the chlorine ion) not form the product with chlorine, but instead revert back to the starting material??
The Chlorine anion is a weaker base than the carboxylate, so the Chlorine is a better leaving group. When the tetrahedral intermediate collapses the Chlorine leaves instead and you end up with the original compound. I hope thats clear, I can try to draw it on chemsketch if its not.
The Chlorine anion is a weaker base than the carboxylate, so the Chlorine is a better leaving group. When the tetrahedral intermediate collapses the Chlorine leaves instead and you end up with the original compound. I hope thats clear, I can try to draw it on chemsketch if its not.
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