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In Williamson ether synthesis for preparing an unsymmetrical ether containing one primary and one tertiary alkyl group, what happens if the alkyl halide used is tertiary?

1. The reaction proceeds slowly because the carbon–halogen bond breaks slowly.
2. An alkene becomes the major product.
3. A symmetrical ether is formed in place of the desired mixed ether.
4. The intended unsymmetrical ether is obtained as the main product.

Correct answer: An alkene becomes the major product.

Solution

Using a tertiary alkyl halide in Williamson ether synthesis often leads to elimination reactions rather than substitution, resulting in the formation of an alkene as the major product due to the steric hindrance that prevents effective nucleophilic attack.

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