Question:medium

Write the structure of (A), (B) and (C) in the following reaction: phenol (C6H5OH) with concentrated HNO3 gives (C); phenol with dilute HNO3 gives (A) + (B).

Show Hint

OH is ortho/para directing: dilute HNO3 gives 2-nitrophenol (A) and 4-nitrophenol (B); concentrated HNO3 gives 2,4,6-trinitrophenol, picric acid (C).
Updated On: Jul 10, 2026
Show Solution

Solution and Explanation

The whole outcome is decided by two facts: the \(-OH\) group steers nitro groups to the 2, 4 and 6 carbons, and the strength of the acid decides how many nitro groups get in.

Dilute nitric acid route: A weak nitrating mixture can only manage a single substitution. Since the free ortho and para sites are both open, phenol gives two mononitro products side by side. One is 2-nitrophenol, where the nitro group sits next to the hydroxyl (this isomer is steam volatile because of intramolecular hydrogen bonding). The other is 4-nitrophenol, with the nitro group directly across the ring (higher boiling, held by intermolecular hydrogen bonds). These are (A) and (B).

Concentrated nitric acid route: A strong nitrating medium keeps substituting until all three activated positions, carbons 2, 4 and 6, carry a nitro group. The final compound is 2,4,6-trinitrophenol, the pale yellow explosive better known as picric acid. This is (C).

Structures in words: (A) hydroxyl on C1 and nitro on C2; (B) hydroxyl on C1 and nitro on C4; (C) hydroxyl on C1 with nitro groups on C2, C4 and C6.
\(\boxed{A = o\text{-nitrophenol},\ B = p\text{-nitrophenol},\ C = \text{picric acid}}\)
Was this answer helpful?
0