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  4. The decreasing order of reactivity towards electrophilic substitution of the following compounds is

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Q. The decreasing order of reactivity towards electrophilic substitution of the following compounds isChemistry Question Image

COMEDKCOMEDK 2015Organic Chemistry – Some Basic Principles and Techniques

Solution:

Due to $+I$ effect of $-CH_3$ group (4) has higher electron density than benzene (1).
Due to strong $-I$ effect of $-Cl$ group and strong $-I$ and $-M$ effects of $-N O_2$ group, both (2) and (3) have lower electron density than benzene (1).
As $-I$ effect of $-Cl$ group is weaker than that of $-NO_2$, (3) has much lower electron density than (2).
Thus the overall reactivity order towards electrophilic substitution is
$4 > 1 > 2 > 3$