[millefiori]

ΘHello,
I am studying organic chemistry independently by working through David Klein's Organic Chemistry as a Second Language.

In this example (attached, 3.16 in the text), is the proton on the far left or the far right of the molecule more acidic?




I would expect that because Cl is more electronegative than F, the C that the Cl atoms are bonded to would have a greater "partial positive" charge than the C which the F atoms are bonded to. If I'm correct, then this carbon would in turn induce a slightly partial negative charge on the C in the far-right carboxyl group, stabilizing its negative charge more than its counterpart on the left.

However the answer key tells me that I'm wrong. What am I misunderstanding?

Thank you for your suggestions!

[Orcio_87]

I would expect that because Cl is more electronegative than F

It's mistake. Fluorine is more electronegative than chlorine atom.

Hydrogen on left side of the molecule will be more acidic.

[millefiori]

Thanks Orcio. Guess I have to revisit the basics!