In the hydrolysis reaction the alkoxide group (nucleophile) attacks the electrop
ID: 826866 • Letter: I
Question
In the hydrolysis reaction the alkoxide group (nucleophile) attacks the electrophillic susbtituent to form the tetrahedral geometry which collapses and causes the other group to leave. I understand the mechanism of the reaction but do not understand why the hydrolysis occurs for the phosphate group (in organophosphate) which is negatively charged and is not electrophillic. Looking around, some sources say that a metal ion cofactor is present to stabilize the charge. Taking that in, how can an electron donating group increase the rate of hydrolysis and an electron withdrawing group decrease the rate? Thanks in advance for the help!
Explanation / Answer
Good question! I'll be glad to explain it.
Withdrawing electrons (electron-withdrawing groups (EWG) increase positive character while an electron donating group will decrease the positive character. Because the hydrolysis reaction is based on the nucleophile attacking the electrophillic substituent, EWG would decrease the rate because it increases positive character of the substituent. Vice versa, the electron donating group decrease positive character (increase negative character of the substituent) and will increase rate of hydrolysis.
Does this make sense? Tell me if you want any more clearification.
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