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Q. Which reagent cannot be used to prepare an alkyl halide from an alcohol ?

Haloalkanes and Haloarenes

Solution:

$NaCl$ is an ionic compound cannot displace $- OH$ by $Cl$. Rest all other reagents $( HCl + ZnCl_2 , PCl_5,SOCl_2 )$ displaces $-OH$ from alcohol and provide $Cl^-$ as a nucleophile.