iodine and fluorine leaving group


by jd12345
Tags: fluorine, iodine, leaving
jd12345
jd12345 is offline
#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
Phys.Org News Partner Chemistry news on Phys.org
First view of nature-inspired catalyst after ripping hydrogen apart provides insights for better, cheaper fuel cells
Following a protein's travel inside cells is key to improving patient monitoring, drug development
Team helps cancer treatment drugs get past their sticking point
aroc91
aroc91 is offline
#2
May5-12, 12:01 PM
P: 160
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


Register to reply

Related Discussions
Hydrogen bonding for Fluorine Chemistry 16
Why is Cl a better leaving group than an anhydride? Biology, Chemistry & Other Homework 1
Questions on synthesizing Fluorine 18 Nuclear Engineering 2
why does neutral fluorine so reactive? Quantum Physics 8
Why does fluorine make compounds volatile? Chemistry 6