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PhF behaves rather differently from other halobenzene derivatives owing to the pi-donor properties of fluoride. For example, the para position is more activated than benzene toward electrophiles. For this reason, it can be converted to 1-bromo-4-fluorobenzene with relatively high efficiency. [3]
Download as PDF; Printable version; In other projects Wikidata item; Appearance. ... Halobenzene may also refer to any of the monosubstituted halobenzenes: Fluorobenzene;
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For example, 2,4-dinitrochlorobenzene reacts in basic solution to give a phenol. Unlike in most other substitution reactions, fluoride is the best leaving group, and iodide the worst. [ 16 ] A 2018 paper indicates that this situation may actually be rather common, occurring in systems that were previously assumed to proceed via S N Ar mechanisms.
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In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution.This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system.
However, another effect that plays a role is the +M effect which adds electron density back into the benzene ring (thus having the opposite effect of the -I effect but by a different mechanism). This is called the mesomeric effect (hence +M) and the result for fluorine is that the +M effect approximately cancels out the -I effect.