Ethers can be prepared by Williamson synthesis in which an alkyl halide is reacted with sodium alkoxide. Di-tertiary ether cannot be prepared by this method. Explain.

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) The Williamson synthesis involves the reaction of an alkyl halide with a strong nucleophile,the alkoxide ion.
Alkoxide ions are strong bases as well as strong nucleophiles.
When a tertiary alkyl halide is used as a substrate,the alkoxide ion acts primarily as a base rather than a nucleophile.
This leads to an elimination reaction (specifically $E2$ mechanism) instead of a substitution reaction.
Consequently,the major product formed is an alkene rather than the desired ether.
For example,the reaction between sodium tert-butoxide and tert-butyl bromide yields $2$-methylpropene as the major product instead of di-tert-butyl ether.

Explore More

Similar Questions

When a $1^o$ alkyl halide reacts with an alkoxide,what is the product obtained?

The substances used for the preparation of ether by Williamson's synthesis are:

The reaction used for the synthesis of ether is

Which of the following on heating gives an ether as the major product?
$(P)$ $C_6H_5CH_2Br + CH_3ONa$
$(Q)$ $C_6H_5ONa + CH_3Br$
$(R)$ $(CH_3)_3CCl + CH_3ONa$
$(S)$ $C_6H_5CH=CHCl + CH_3ONa$

Write the names of reagents and equations for the preparation of the following ethers by $Williamson$ synthesis:
$(i)$ $1-Propoxypropane$
$(ii)$ $Ethoxybenzene$
$(iii)$ $2-Methoxy-2-methylpropane$
$(iv)$ $1-Methoxyethane$

Difficult
View Solution

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo