Explain why $C l_{2} C = C C l_{2}$ does not add $C l_{2}$ under usual conditions but adds in the presence of $A l C l_{3}$ ?

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Solution

Due to the electron withdrawing effect of four $C l$ atoms, the $e^{-}$ density or nucleophilicity of πe¯'s of the alkene decreases. So, electrophilic reaction does not take place (even does not show the test for unsaturation, i.e., Bayer's test and decolourisation of $B r_{2}$ solution).
$A l C l_{3}$ reacts with $C l_{2}$ and polarises $C l_{2}$ to $C l^{+}$ and increases the electrophilic character of $C l^{+}$ that can react efficiently.

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