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Iodine and fluorine leaving group

by jd12345
Tags: fluorine, iodine, leaving
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jd12345
#1
May5-12, 05:29 AM
P: 260
A question in my test asked which of the acyl halide will hydrolyse faster in an aqueous solution of NaOH

Well the asnwer is acyl iodide becasue iodine is a better leaving group( the solution says so)
But i dont understand - fluorine will be hydrated to the greatest extent so removal of fluorine should be easy
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aroc91
#2
May5-12, 12:01 PM
P: 161
Quote Quote by jd12345 View Post
fluorine will be hydrated to the greatest extent so removal of fluorine should be easy
That doesn't necessarily make it more stable, though. The charge dispersion due to iodide's size makes it far more stable on its own than fluoride.

This is the same concept as halide acid strength increasing as you move down the row. Check the halide acid pKas yourself-

evans.harvard.edu/pdf/evans_pka_table.pdf


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