# Why can't HCl be used in chlorination of alkane?

Is it because the HCl bond is strong or it is because we have to form HCl at the product side during the propagation step?

• HCl can't be used because it just won't chlorinate alkanes, no matter how hard you persuade it. Why would it, really? – Ivan Neretin Apr 14 '17 at 10:16

$\ce{HCl}$ is not used in chlorination of any alkane as the bond between them is highly polar which dissociates to give $\ce{H+}$ and $\ce{Cl-}$ that will not be able to initiate the formation of free radicals in alkane. In this case $\ce{H+}$ will be released from the alkane as carbon is more electronegative than hydrogen. Chloride ion formed will again react with $\ce{H+}$ ion to form $\ce{HCl}$ as it will feel a replusion from carbon due to the lone pair. Hence no chlorination takes place so $\ce{HCl}$ is generally avoided.