S_N2 reactions of simple carboxylate ions with haloalkanes in aqueous solution generally do not give good yields of esters. 

(a) Explain why this is so. 

(b) Reaction of 1-iodobutane with sodium acetate gives an excellent yield of ester if carried out in acetic acid (as shown here). Why is acetic acid a better solvent for this process than water? 

(c) The reaction of 1-iodobutane with sodium dodecanoate proceeds surprisingly well in aqueous solution, much better than the reaction with sodium acetate (see the following equation). Explain this observation.

Transcribed Image Text:

CH,CO,H, 100°C CH;CH,CH,CH,I + CH,CO¯N * CH;CH,CH,CH,OCCH3 + Na*I 95% 1-lodobutane Sodium acetate Butyl acetate