[moondaughter]

http://i47.tinypic.com/k9gdug.jpg

this is the reaction, my professor but it up in class but never solved it! I would really appreciate any *delete me* I know that I'll make an enamine during the first step, but I'm unsure of whether the enamine will displace the chlorine or whether it will add to the carbonyl group, and then what does the acid do at the end?

[Dan]

Leaving groups a to carbonyls are highly cativated towards S_N2 - so I would expect substitution of chloride.

What product does that give you? How might that react with aqueous HCl?

[orgopete]

I think sometimes a good trick to determine whether a reaction might occur is to just try it. Draw the addition of the enamine to the carbonyl group. Would it be stable? Would it reverse? Can triethylamine add to the carbonyl group of an ester?