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Comparing Rate of Hydrolysis of Acyl halides
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+ Nucleophilicity
+ Kinetics
+ Chemistry
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Kiran Kelkar
Comparing Rate of Hydrolysis of Acyl halides
The high reactivity of acyl chlorides towards nucleophilic attack is due to the highly polarised situation of the carbon-oxygen/chlorine bonds i.e.
As you have mentioned due to the phenyl ring being planar, the steric hindrance does not overpower the polarising thing.
Now on comparing the reactions -NO$_2$ group's -M effect will be the most successful to make the carbon-oxygen/chlorine bonds more polar as compared to methyl's +I effect.
The high reactivity of acyl chlorides towards nucleophilic attack is due to the highly polarised situation of the carbon-oxygen/chlorine bonds i.e.
As you have mentioned due to the phenyl ring being planar, the steric hindrance does not overpower the polarising thing.
Now on comparing the reactions -NO$_2$ group's -M effect will be the most successful to make the carbon-oxygen/chlorine bonds more polar as compared to methyl's +I effect.
@RobinSingh the paper is not explicitly showing any comparison between p-nitro benzoyl chloride and acetyl chloride. It does talks about ethyl p-nitrobenzoate which is a different compound.More
The high reactivity of acyl chlorides towards nucleophilic attack is due to the highly polarised situation of the carbon-oxygen/chlorine bonds i.e.
As you have mentioned due to the phenyl ring being planar, the steric hindrance does not overpower the polarising thing.
Now on comparing the reactions -NO$_2$ group's -M effect will be the most successful to make the carbon-oxygen/chlorine bonds more polar as compared to methyl's +I effect.
The high reactivity of acyl chlorides towards nucleophilic attack is due to the highly polarised situation of the carbon-oxygen/chlorine bonds i.e.
As you have mentioned due to the phenyl ring being planar, the steric hindrance does not overpower the polarising thing.
Now on comparing the reactions -NO$_2$ group's -M effect will be the most successful to make the carbon-oxygen/chlorine bonds more polar as compared to methyl's +I effect.
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