[Marcus]

How would the reaction between chloroacetic acid and something like this proceed?

ClCH₂COOH + Ph-O^-Na⁺ ---->

I'm predicting :

PH-O-CH₂-CO₂H + NaCl...

Is this correct? or would the reaction site occur at the carbonyl?

[eclecticmess07]

Hi Marcus.  Bet you $20 you're in my class.

Think pKa...

Thanks for posting the question about the NMR.  Was struggling with that myself. 

[Marcus]

Section 408?

Anyway, with pKa in mind, I'm guessing then an acid-base reaction...

ClCH₂COOH + Ph-O^-Na⁺ (essentially) ---->

ClCH₂COO^-Na⁺ + Ph-OH

Since, chloroacetic acid is the stronger acid, and phenolate is the stronger base they're favored to react and produce chloroacetate and phenol? Is that where you were going? Or am I completely off track?

[eclecticmess07]

hah.  right class, wrong section (I'm in 406).

And yes, I'd say it's a straight-forward acid-base rxn, since that's the whole point of adding sodium hydroxide in to fully deprotonate o-cresol.  Adding an acid would just reverse the first reaction step. 

Can't wait for spring break.  ::sigh::