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Which of the following is most reactive toward nucleophilic aromatic substitution (hydrolysis)?

Which of the following groups exerts a strong deactivating effect on an aromatic ring?

The following transformation proceeds through:

The presence of the chlorine atom on the benzene ring makes the second substituent enter at which position?

What is the product $Z$ in the following reaction sequence?
$C_6H_5N_2Cl$ $\xrightarrow{Cu_2Cl_2/HCl} X$ $\xrightarrow{CH_3Cl/Na, \text{dry ether}} Y$ $\xrightarrow{Cl_2/Fe, \text{dark}} Z$

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