Does anyone know the detailed reaction mechanism pathway for the hydroxide ion catalysed hydrolysis of ester that produced a OOCR- leaving group? Thanks.
Name:
chem guy2008-09-22 10:20
Ehm, ester hydrolysis will be hydroxide promoted, not catalyzed (as least how I learned it). In any case, take a general ester such as RCOOR'. The -OH nucleophile will attack the carbonyl carbon of the ester. This produces a tetrahedral intermediate containing the R group, a hydroxyl group, an alkoxy group (OR') and finally the charged (-)O- (former carbonyl oxygen). The second step involves collapse of the tetrahedral intermediate when -O(-) electrons reform the C=O double bond, and one of the groups will be expelled, either OH or OR'. When -OR' is expelled, an acid-base reaction ensues and deprotonates the carboxylic acid, forming RCOO- + R'OH. Hope this helped you.
Notice this reaction if more formally referred to as hydroxide "promoted", since -OH is not re-formed at any step in the reaction.
Okayy bitchezz its Maths , liekk math is sooo fun and awesome u noee cuntzz its like Omg it mathz toimee , likee yee u noe fun singing ur times tablezz , yee fun fun ayezz :P