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The product (P) formed from the following multistep reaction is:
Step (i): Bromination ($$\text{Br}_2$$)
When 4-nitrotoluene reacts with $$\text{Br}_2$$, electrophilic aromatic substitution occurs. We must look at the directing influence of both groups to determine where the bromine atom ($$\text{-Br}$$) will attach:
Because both groups reinforce each other, the bromine atom is introduced ortho to the methyl group and meta to the nitro group.
$$\text{Intermediate 1} = \text{2-bromo-4-nitrotoluene}$$
Step (ii): Reduction ($$\text{H}_2 / \text{Pd}$$)
Catalytic hydrogenation using hydrogen gas over a palladium catalyst ($$\text{H}_2/\text{Pd}$$) selectively reduces the strongly electrophilic nitro group ($$\text{-NO}_2$$) into an amino group ($$\text{-NH}_2$$). The ring-bound bromine and methyl groups remain unaffected under these typical conditions.
$$\text{Intermediate 2} = \text{3-bromo-4-methylaniline}$$
Step (iii): Diazotization ($$\text{NaNO}_2, \text{HCl}, 0^\circ\text{C}$$)
Reacting a primary aromatic amine ($$\text{-NH}_2$$) with nitrous acid (generated in situ from $$\text{NaNO}_2$$ and $$\text{HCl}$$) at a low temperature ($$0^\circ\text{C} - 5^\circ\text{C}$$) converts the amino group into a highly reactive diazonium salt group ($$\text{-N}_2^+\text{Cl}^-$$).
$$\text{Intermediate 3} = \text{3-bromo-4-methylbenzenediazonium chloride}$$
Step (iv): Deamination ($$\text{H}_3\text{PO}_2$$)
Hypophosphorous acid ($$\text{H}_3\text{PO}_2$$) acts as a mild reducing agent that replaces the diazonium group ($$\text{-N}_2^+$$) with a hydrogen atom ($$\text{-H}$$), releasing nitrogen gas ($$\text{N}_2$$). This effectively removes the original functional group at that position entirely.
Therefore, the final product (P) is 2-bromotoluene (also called o-bromotoluene).
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