12.53 b

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Hannah Chew 2A
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Joined: Fri Sep 29, 2017 7:05 am
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12.53 b

Postby Hannah Chew 2A » Fri Dec 08, 2017 8:43 pm

I know this question has been asked several times, but I am still very confused about why formic acid is stronger than acetic acid. The solution manual and previous forums talk about electron donating properties and electron withdrawing. I'm not sure what these mean.

1) Why does the CH3 group in acetic acid have electron donating properties? How can you tell by looking at the lewis structure?
2) Why is the H attached to the carboxyl group in formic acid more electron withdrawing than the CH3 group in acetic acid, and how do you know?

Any help is appreciated:)

David Zhou 1L
Posts: 61
Joined: Fri Sep 29, 2017 7:04 am

Re: 12.53 b

Postby David Zhou 1L » Sun Dec 10, 2017 3:12 am

The methyl group of acetic acid has greater electron donating power than the single H in formic acid, meaning it destabilizes the carboxylate anion - the anion already has a negative charge on it, and so the slightly higher electron donating power of the methyl group repels against that.

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