Oxygen and sulfur as nucleophiles ethers, esters, thioethers, epoxides

2 Oxygen and sulfur as nucleophiles ethers, esters, thioethers, epoxides 

Alkyl halides can react with water or alcohols by either Sn2 or SnI mechanisms to give alcohols or ethers respectively. 

It is often preferable to use basic conditions with hydroxide or alkoxide as a better nucleophile, though this may lead to elimination and alkene formation as a competing reaction (see Section 6.4). 

Although a carboxylate anion is only a relatively modest nucleophile (see Section 6.1.2), it is possible to exploit an Sn2 reaction to prepare esters from carboxylic acids as an alternative to the usual esterification methods (see Section 7.9). Such methods might be useful, depending upon the nature and availability of starting materials. 

Sulfur nucleophiles behave similarly to oxygen compounds. Again, the anion will be a better 

---