To prepare di tert butyl ether a tertiary Halide(tert butyl halide) is required but williamson ether synthesis does not forms di tert butyl ether be cause of di tert butyl ether under goes elimination or substitution and forms alkenes

Why di-tert-butyl ether cannot be prepared by Williamson's synthesis?

Williamson's synthesis is a well-known method for the preparation of ethers. This method involves the reaction between an alkoxide ion and an alkyl halide. However, di-tert-butyl ether cannot be prepared by this method due to several reasons.

Steric hindrance

The primary reason for the failure of Williamson's synthesis in the preparation of di-tert-butyl ether is steric hindrance. The tert-butyl group is bulky and hinders the reaction between the alkoxide ion and the alkyl halide. The tert-butyl group occupies a lot of space and makes it difficult for the reaction to occur.

Unstable intermediate

Another reason for the failure of Williamson's synthesis is the unstable intermediate that is formed during the reaction. The intermediate formed during the reaction of an alkoxide ion with an alkyl halide is an oxonium ion. In the case of di-tert-butyl ether, the oxonium ion formed is highly unstable due to steric hindrance. The tert-butyl groups prevent the stabilization of the oxonium ion, which leads to the failure of the reaction.

Low nucleophilicity of alkoxide ion

The alkoxide ion used in Williamson's synthesis is a weak nucleophile. The weak nucleophilicity of the alkoxide ion makes it difficult for it to react with the alkyl halide. In the case of di-tert-butyl ether, the reaction is even more difficult due to steric hindrance.

Alternative methods

Although Williamson's synthesis cannot be used to prepare di-tert-butyl ether, there are alternative methods available. One such method is the acid-catalyzed dehydration of tert-butanol. This method involves the removal of a water molecule from tert-butanol to form di-tert-butyl ether.

Conclusion

In conclusion, di-tert-butyl ether cannot be prepared by Williamson's synthesis due to steric hindrance, the formation of an unstable intermediate, and the low nucleophilicity of the alkoxide ion. However, alternative methods such as acid-catalyzed dehydration can be used to prepare di-tert-butyl ether.