Some $meta$-directing substituents in aromatic substitution are given. Which one is most deactivating?

Nitrating mixture is

Among the following,the aromatic compound is:

When excess $C_6H_6$ is reacted with $CH_2Cl_2$ in the presence of anhydrous $AlCl_3$,which of the following products is obtained?

The reaction of benzene with a mixture of concentrated $HNO_3$ and concentrated $H_2SO_4$,followed by treatment with $Cl_2 / FeCl_3$,gives:

Decide the correct order of reactivity of the following compounds towards electrophilic aromatic substitution (halogenation) with $(Cl_2 + AlCl_3)$:
$I$: Phenyl benzoate $(C_6H_5COOC_6H_5)$
$II$: Toluene $(C_6H_5CH_3)$
$III$: Ethylbenzene $(C_6H_5CH_2CH_3)$
$IV$: Benzene $(C_6H_6)$