Question

Question: Draw at least ten more resonance structures for acetaminophen, the active pain reliever in Tylenol.

Short answer

Answer

The ten resonance structures are shown below:

Step-by-step solution

Step-by-Step Solution Step 1: Meaning of resonance

When the single Lewis structure cannot fulfill the structure of the compound, contributing structures are given for the compounds. These contributing structures are known as resonance structures.

 Step 2: Formation of resonance structures

The arrow's movement between the lone pair on nitrogen and oxygen of the carbonyl group gives rise to the following resonance structures.

Resonance structures

The arrow's movement between oxygen and benzene ring gives rise to the following resonance structures.

Resonance structures

The remaining resonance structures

Resonance structures