Which statement best describes the directing effects of the substituents on salicylamide during electrophilic aromatic substitution reactions?

• A. Both the amide group and the hydroxyl group are $\text{ortho}$/$\text{para}$-directing, increasing reactivity at positions $\text{ortho}$ and $\text{para}$ to each group.
• B. The amide group is $\text{ortho}$/$\text{para}$-directing and activates the ring, while the hydroxyl group is $\text{meta}$-directing and deactivates the ring.
• C. Both the amide group and the hydroxyl group are $\text{meta}$-directing, decreasing reactivity at $\text{ortho}$ and $\text{para}$ positions.
• D. The hydroxyl group is $\text{ortho}$/$\text{para}$-directing and activates the ring, while the amide group is $\text{meta}$-directing and deactivates the ring.

Answer: (D)

Verified step by step guidance

1. Identify the substituents on salicylamide: it contains a hydroxyl group (-OH) and an amide group (-CONH2) attached to the aromatic ring.
2. Recall the directing effects of common substituents in electrophilic aromatic substitution (EAS): activating groups with lone pairs (like -OH) are typically ortho/para-directing and increase ring reactivity, while groups that withdraw electron density (like some amides) can be meta-directing and deactivate the ring.
3. Analyze the hydroxyl group (-OH): it donates electron density through resonance, stabilizing the intermediate carbocation formed during EAS, thus it is an activating, ortho/para-directing group.
4. Analyze the amide group (-CONH2): although it has a lone pair on nitrogen, the resonance with the carbonyl group withdraws electron density from the ring, making it a deactivating, meta-directing substituent.
5. Combine these effects to understand that in salicylamide, the hydroxyl group directs electrophiles to the ortho and para positions relative to itself and activates the ring, while the amide group directs electrophiles to the meta position relative to itself and deactivates the ring.