[baum0372]

I was reading the Org Syn procedure for making chloroacetamide from ethyl chloroacetate and ammonium hydroxide (Org. Synth. 1927, 7, 16) and it appeared to me that the reaction should not really work.

I though the ammonia would substitute for the chlorine rather than on the ester forming the ethyl ester of glycine as the final product.  I was surprised to find that the product is chloroacetamide.  Is there a reason that the amine substitutes for the ester over the chlorine?  Thanks.

[orgopete]

Since glycine can be prepared by reacting chloroacetic acid with ammonia, the lack of substitution cannot be because the reaction is somehow unable to take place. I therefore assume the formation of the chloroacetamide indicates the attack on the carbonyl group is simply faster than the substitution reaction. Without looking up the Org Syn prep, I assume it has been optimized for the amide formation and removal of any substitution product that may have formed.