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Chapter 1: Q81. (page 59)

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

Short Answer

Expert verified

Answer

The ten resonance structures are shown below:

Step by step solution

01

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.

02

 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

03

The remaining resonance structures

Resonance structures

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Most popular questions from this chapter

Question: The unmistakable odor of a freshly cut cucumber is largely due to cucumber aldehyde. (a) How many sp2hybridized carbon atoms does cucumber aldehyde contain? (b) What is the hybridization of the O atom? (c) What orbitals are used to form the carbon-oxygen double bond? (d) How many σbonds does cucumber aldehyde contain? (e) How many bonds does it contain?

Question: Which of the given resonance structures (A, B, or C) contributes most to the resonance hybrid? Which contributes the least?

Question: Which of the bond shown in red in each compound or pair of compounds is shorter?

a.

b.

c.

d.

Question: Rank the following bonds in order of increasing bond length.

Question: Convert each molecule into a skeletal structure.

a.

b.

c.

d.
See all solutions

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