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Title: How do I tell which substituted cyclic compound will undergo the most rapid nucleophilic substitution? Post by: dauterjudy938 on Sep 23, 2012 I was given a set of cyclic compounds: bromobenzene, 1-chloro-4-anisol (I think, a benzene ring with a Cl and OCH3 para to each other), 1-chloro-4-nitrobenzene, and 1-fluoro-4-methylbenzene
The one that will undergo the most rapid nucleophilic substitution with hydroxide ion is the 1-chloro-4-nitrobenzene, but I don't get why and there is a final soon so it's important. Please explain so I can learn and get it, thanks! :) Title: How do I tell which substituted cyclic compound will undergo the most rapid nucleophilic substitution? Post by: Datchile on Sep 23, 2012 p-Cl-C6H4-NO2 has a strongly electron-withdrawing group opposite a good leaving group, Cl. So that is most reactive with OH-. There is strong (+) charge on the benzene carbon next5 to Cl.
CH3O- is electron donating, so that is useless when considering reactivity of p-Cl-C6H4-OCH3 with OH-. p-Fluorotoluene is also a poor competitor. |