Question

Consider the following reaction

Identify the correct order for percentage yield of the products A, B and C

• A. C > B > A
• B. A > B > C
• C. B > A > C
• D. B > C > A

Answer 1

Answer: (C)

B > A > C

Answer 2

In concentrated HNO₃/H₂SO₄, the –NH₂ group is protonated to –NH₃⁺, which is a deactivating, meta-directing group. Therefore, nitration predominantly occurs at the meta position. Among the remaining positions, the para is less sterically hindered than the ortho. Hence the order of yield is:

$$\text{Meta (B)} > \text{Para (A)} > \text{Ortho (C)}$$

Thus, option (3) (B > A > C) is correct.

Under strongly acidic conditions, –NH₂ is protonated to –NH₃⁺ (meta-directing). Thus, substitution occurs mainly at the meta position (B). Para (A) is favored over sterically hindered ortho (C), giving B > A > C.