Iodine and fluorine leaving group

In summary, acyl iodide will hydrolyse faster in an aqueous solution of NaOH due to iodine being a better leaving group and the charge dispersion of iodide's size making it more stable. This concept is similar to the trend of halide acid strength increasing as you move down the row.
  • #1
jd12345
256
2
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 don't understand - fluorine will be hydrated to the greatest extent so removal of fluorine should be easy
 
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  • #2
jd12345 said:
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
 

FAQ: Iodine and fluorine leaving group

What is the difference between iodine and fluorine leaving groups?

Iodine and fluorine are both halogen atoms that can act as leaving groups in a chemical reaction. The main difference between them is their atomic size, with iodine being larger and fluorine being smaller. This affects their reactivity and ability to stabilize a negative charge, with iodine being a better leaving group due to its larger size and ability to disperse the negative charge better.

How does the leaving group ability of iodine and fluorine affect a chemical reaction?

The leaving group ability of iodine and fluorine plays a crucial role in a chemical reaction, as it determines the rate at which the reaction takes place. Iodine, being a better leaving group, can stabilize the negative charge better and therefore, increases the rate of the reaction. On the other hand, fluorine, being a smaller leaving group, may not be able to stabilize the negative charge as effectively, resulting in a slower reaction rate.

Can iodine and fluorine leaving groups be interchanged in a reaction?

In most cases, iodine and fluorine leaving groups cannot be interchanged in a reaction. This is because the size difference between them results in different reactivity and stability in a reaction. However, there are some exceptions where fluorine can act as a better leaving group in certain reactions, such as in nucleophilic substitution reactions.

How does the leaving group ability of iodine and fluorine affect the solubility of a compound?

The leaving group ability of iodine and fluorine can also impact the solubility of a compound in a solvent. Generally, compounds with iodine leaving groups tend to be more soluble in polar solvents, while compounds with fluorine leaving groups are more soluble in nonpolar solvents. This is due to the difference in their electronic properties and ability to interact with the solvent molecules.

What are some common reactions that involve iodine and fluorine leaving groups?

Iodine and fluorine leaving groups are commonly involved in substitution and elimination reactions, such as SN1, SN2, and E1 reactions. They are also frequently used in organic synthesis, particularly in reactions involving halogenation, where they can be substituted for other leaving groups such as chlorine or bromine. Additionally, iodine and fluorine leaving groups are commonly found in pharmaceutical compounds, where their reactivity and stability play a crucial role in drug design and development.

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