DISCUSSION

Ethers are important class of compounds which are

particularly useful as solvents. They appear in the structures of

insecticides and medicines. The Williamson Ether Synthesis is a

method used in synthesizing ethers discovered by Alexander

Williamson, a British chemist. This is a nucleophilic aliphatic

substitution at a saturated carbon which is used in preparing

ethers where an alkoxide ion or a phenoxide ion acts as a

nucleophile attacking the saturated carbon (Gunawardena).

Moreover, this reaction involves an alkoxide which reacts with a

primary haloalkane or a sulfonate ester through an SN2

mechanism, therefore, allowing the formation of asymmetric

ethers (ethers with two different R groups). However, because

Williamson Ether Synthesis has all of the limitations associated

with SN2 reactions, the substrate which reacts with the alkoxide

should be unhindered or naked to prevent elimination. This

explains why primary or methyl substrates are best suited for this

reaction.

The SN2 pathway is a nucleophilic aliphatic substitution at a

saturated carbon which involves a leaving group and a

nucleophile. In the designation SN2, S stands for substitution, N

for nucleophilic, and 2 bimolecular which means both the

nucleophile and the haloalkane are involved in the rate-

determining step (Brown, et al. 2012). This reaction is favored by

polar aprotic solvents-those that lack hydrogen-bond donating

capability- in which they proceed faster. SN2 reactions also work

best with strong nucleophile and primary or methyl halides; a less

powerful nucleophile means a slower SN2 reaction.

The general features of Williamson ether synthesis include

preparing alkali metal alkoxides of simple aliphatic primary,

secondary, and tertiary alcohols by using strong bases; and

preparing alkali metal salts of phenols through reaction with weak

bases. These alkoxides and phenoxides act as nucleophiles

during the nucleophilic substitution reaction. In the experiment, a

carboxylic acid was used instead of alcohol.