[alphaomega]

For the reaction below, I've shown what I think will happen but I'm not sure if the OCCH3 will somewhere dissociate from the O connected to the carbon.  Or I could be completely wrong in which case feel free to completely correct me.

My thinking was that the Cl would leave (although I'm not sure how the Carboxylic Acid does that) and then the O- would attack.

Again, I welcome all advise and thank you very much.

[alphaomega]

After posting that I realize that there are three things in there that aren't that easy to read.  First off, that's a Cl bonded to C in the original molecule.  Then the reagents are Na+, CH3C=O
                                      |
                                      O-
, and CH3C=O
              |
              OH
Finally, that's an H coming out of the screen in the final product.  My apologies for the poor picture.

[Dan]

Is acetate a good nucleophile? Are you sure this will be Sn2?

[UWSteve]

My thinking was that the Cl would leave (although I'm not sure how the Carboxylic Acid does that) and then the O- would attack.

For Sn2 reactions, the nucleophile attacks the substrate from the backside (opposite of the leaving group). This results in a partial positive charge on the central carbon and a partial negative charge on the leaving group (in the transition state). To compensate, the carbon-leaving group bond breaks and forms an anion. Also, remember that the final configuration needs to be inverted relative to the initial configuration (remember backside attack).




As for what Dan said, I thought acetate should work. Secondary carbons favor the Sn2 mechanism with weakly basic nucleophiles. However, I'm probably overlooking something (it's past my bed time ).