Conditions: 0.5 mL of 0.05 M Br2 in 90% AcOH, added to 0.5 mL of 0.25 M solution of aryl compound in 90% AcOH. Refluxed at 100˚ C for
10 minutes.
A significantly greater color change was observed in the benzoate than the m-xylene, indicating faster bromination. Aren't carboxylic esters
relatively strong deactivating groups in electrophilic aromatic substitution? meta-xylene has two activating groups. Why doesn't its reactivity in
these conditions dwarf methyl benzoate?
I'm being led to believe the answer is related to resonance, but I fail to see how a resonance effect could overcome the ∂+ on the
carbonyl carbon.Nicodem - 20-3-2013 at 08:37
A significantly greater color change was observed in the benzoate than the m-xylene, indicating faster bromination.
You are basing your conclusions on a non-existing evidence. I suggest you to stick to the scientific method when evaluating experimental results: no
evidence, no conclusions.
