(a) Interpretation: All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn. Concept introduction: Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same. The resonance hybrid is a weighted average of all resonance structures.

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Answer 1

Question

Chapter 1, Problem 1.79P

Interpretation Introduction

(a)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(b)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(c)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(d)

Interpretation:

All the resonance structures of each of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

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Draw all of the resonance structures for each of the following species. Be sure to include the curved arrows that indicate which pairs of electrons are shifted in going from one resonance structure to the next. Draw the resonance hybrid of each species. (a) ОН (b) (c) H3C

(a) Draw all resonance contributors of the following ion. In drawing each additional resonance structure, use curved arrows to indicate which pairs of electrons are being shifted. (b) Draw the resonance hybrid. (c) Which c–C bond is the longest?

QUESTION 4. (a) Below are two structural isomers. Interestingly, one of these structures is significantly more acidic than the other. Circle the most acidic proton in each. Determine which structure is more acidic and explain why. Use your knowledge of resonance structures and molecular geometry to support your argument. NO₂ NO₂ OH OH

Answer 2

Question

Chapter 1, Problem 1.79P

Interpretation Introduction

(a)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(b)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(c)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(d)

Interpretation:

All the resonance structures of each of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

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Answer 3

Question

Chapter 1, Problem 1.79P

Interpretation Introduction

(a)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(b)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(c)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(d)

Interpretation:

All the resonance structures of each of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

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Answer 4

Question

Chapter 1, Problem 1.79P

Interpretation Introduction

(a)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(b)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(c)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(d)

Interpretation:

All the resonance structures of each of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

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Answer 5

Chapter 1, Problem 1.79P

Interpretation Introduction

(a)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(b)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(c)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Interpretation Introduction

(d)

Interpretation:

All the resonance structures of each of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Answer 6

Chapter 1, Problem 1.79P

Interpretation Introduction

(a)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Answer 7

Chapter 1, Problem 1.79P

Interpretation Introduction

(a)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Answer 8

Interpretation Introduction

(b)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Answer 9

Interpretation Introduction

(b)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Answer 10

Interpretation Introduction

(c)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Answer 11

Interpretation Introduction

(c)

Interpretation:

All the resonance structures of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Answer 12

Interpretation Introduction

(d)

Interpretation:

All the resonance structures of each of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Answer 13

Interpretation Introduction

(d)

Interpretation:

All the resonance structures of each of the given specie are to be drawn, with curved arrows indicating which electrons are shifted. The resonance hybrid of the specie is to be drawn.

Concept introduction:

Resonance structures are alternate valid Lewis structures in which pi electrons and/or lone pair electrons are distributed in different positions. Resonance structures must follow the usual rules of Lewis structures. The connectivity of the atoms must remain the same.

The resonance hybrid is a weighted average of all resonance structures.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 1 - Prob. 1.1P Ch. 1 - Prob. 1.2P Ch. 1 - Prob. 1.3P Ch. 1 - Prob. 1.4P Ch. 1 - Prob. 1.5P Ch. 1 - Prob. 1.6P Ch. 1 - Prob. 1.7P Ch. 1 - Prob. 1.8P Ch. 1 - Prob. 1.9P Ch. 1 - Prob. 1.10P

Solution Summary: The author explains that the resonance hybrid is a weighted average of all these resonance structures, with the charge delocalized mostly on C1, C3, and C5.

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Chapter 1 Solutions