Question:
Identify the major product of the following reaction sequence:
Identify the major product of the following reaction sequence:
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–NO\(_2\) is meta-directing; –NH\(_2\) is ortho/para directing after reduction, which changes substitution pattern in later steps.
Updated On: Jul 18, 2026
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The Correct Option is A
Solution and Explanation
Step 1: First step – Nitration of benzene.
Benzene reacts with conc. HNO\(_3\)/conc. H\(_2\)SO\(_4\) at 323–333 K to form nitrobenzene: \[ C_6H_6 \rightarrow C_6H_5NO_2 \] Nitro group is a strong deactivating and meta-directing group.
Step 2: Second step – Chlorination.
Chlorination with Cl\(_2\)/AlCl\(_3\) occurs on nitrobenzene. Since –NO\(_2\) is meta-directing, chlorine enters the meta position: m-chloronitrobenzene is formed
Step 3: Third step – Reduction.
H\(_2\)/Pd-C reduces –NO\(_2\) group to –NH\(_2\): \[ C_6H_4ClNO_2 \rightarrow C_6H_4ClNH_2 \] This gives chloroaniline.
Step 4: Directing effect after reduction.
–NH\(_2\) is a strong ortho/para directing group. Therefore, substitution pattern leads mainly to ortho/para chloroaniline, with ortho product being significant due to reaction conditions.
Step 5: Identify major product.
Considering activation after reduction and stability, the major product corresponds to ortho-chloroaniline type structure.
Step 6: Final conclusion.
\[ \boxed{\text{o-chloroaniline (major product)}} \]
Benzene reacts with conc. HNO\(_3\)/conc. H\(_2\)SO\(_4\) at 323–333 K to form nitrobenzene: \[ C_6H_6 \rightarrow C_6H_5NO_2 \] Nitro group is a strong deactivating and meta-directing group.
Step 2: Second step – Chlorination.
Chlorination with Cl\(_2\)/AlCl\(_3\) occurs on nitrobenzene. Since –NO\(_2\) is meta-directing, chlorine enters the meta position: m-chloronitrobenzene is formed
Step 3: Third step – Reduction.
H\(_2\)/Pd-C reduces –NO\(_2\) group to –NH\(_2\): \[ C_6H_4ClNO_2 \rightarrow C_6H_4ClNH_2 \] This gives chloroaniline.
Step 4: Directing effect after reduction.
–NH\(_2\) is a strong ortho/para directing group. Therefore, substitution pattern leads mainly to ortho/para chloroaniline, with ortho product being significant due to reaction conditions.
Step 5: Identify major product.
Considering activation after reduction and stability, the major product corresponds to ortho-chloroaniline type structure.
Step 6: Final conclusion.
\[ \boxed{\text{o-chloroaniline (major product)}} \]
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