killswitch
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Why is methyl benzoate more reactive to EAS bromination than m-xylene?
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.
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Nicodem
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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.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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bfesser
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Thread Moved
9-7-2013 at 14:51 |
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