Wurtz reaction fails in case of tertiary alkyl halides. Explain.

Answer : In Wurtz reaction, alkyl halides react with metallic sodium in presence of dry ether to give symmetrical alkanes containing double the number of carbon atoms present in the alkyl halide. Wurtz reaction

This reaction generally fails with tertiary alkyl halides because instead of undergoing Wurtz reaction, tertiary alkyl halides prefer to undergo dehydrohalogenation in presence of a strong base such as Na .

It should be noted that the ease of dehydrohalogenation of alkyl halide follows the order : tertiary > secondary > primary. Hence, primary and secondary alkyl halides undergo Wurtz reaction while tertiary alkyl halides undergo dehydrohalogenation to form alkenes.

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