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? asked in Science & MathematicsChemistry · 8 years ago

Which proton in ethyl acetate is more acidic and why?

Ethyl acetate: CH3-COO-CH2CH3

I think the CH3 at the very left is more acidic because the CH3 at the very right is donating electrons to the CH2, thereby allowing CH2 to retain its electrons. However, at the same time, the CH2 is attached directly to an oxygen and there's another oyxgen atop the carbon, so maybe inductive effects play a role here, too, making CH2 more acidic?

But then the CH3 at the very right is donating its electrons, at the same time also has its electrons being induced by the two Os, so even though it is farther from the two Os, that one's more acidic?

Yeah, you just heard my brain fart.

Thanks for any advice!

1 Answer

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  • DrBob1
    Lv 7
    8 years ago
    Favorite Answer

    Loss of a proton from the carbon of the acid gives an anion stabilized by resonance with the carbonyl group. This makes it much more acidic.

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