Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 5, Problem 6E

(a)

Interpretation Introduction

Interpretation:The resonance structure that results from curved arrows mentioned below should be determined.

  Organic Chemistry: A Guided Inquiry, Chapter 5, Problem 6E , additional homework tip  1

Concept introduction:When one single structure is unable to describe all the properties of single molecule, a phenomenon called resonance comes into play. This arises when two or more than two Lewis structures are possible for one molecule. All such structures are called resonating structures and have same placement of atoms in them but these have different locations of bond pairs and lone pairs. The resonating structures are inter-convertible with each other. The resultant of all the resonating or contributing structures is called the resonance hybrid.

Rules to form resonance structure are as follows:

1. Use arrow types 1 and 2 for resonance structure of anions in movement of negative charge. Arrow type 1 shows the movement of lone pair toward adjacent atom and then converted into π bond. Arrow type 2 shows the movement of π electron pair from double bond towards adjacent carbon and then converted into lone pair.

2. Use only arrow type 3 to move a positive charge for resonance structure of cations. Arrow type 3 is used to move π electron pair towards adjacent single bonds.

3. The sigma bond should not be broken. Any atom must not move from its place and total number of electrons must be same in all resonance structures.

(b)

Interpretation Introduction

Interpretation:Whether the use of arrow type 3 in resonance structure of anion skips the important resonance structure or not should be determined.

Concept introduction:When one single structure is unable to describe all the properties of single molecule, a phenomenon called resonance comes into play. This arises when two or more than two Lewis structures are possible for one molecule. All such structures are called resonating structures and have same placement of atoms in them but these have different locations of bond pairs and lone pairs. The resonating structures are inter-convertible with each other. The resultant of all the resonating or contributing structures is called the resonance hybrid.

Rules to form resonance structure are as follows:

1. Use arrow types 1 and 2 for resonance structure of anions in movement of negative charge. Arrow type 1 shows the movement of lone pair toward adjacent atom and then converted into π bond. Arrow type 2 shows the movement of π electron pair from double bond towards adjacent carbon and then converted into lone pair.

2. Use only arrow type 3 to move a positive charge for resonance structure of cations. Arrow type 3 is used to move π electron pair towards adjacent single bonds.

3. The sigma bond should not be broken. Any atom must not move from its place and total number of electrons must be same in all resonance structures.

(c)

Interpretation Introduction

Interpretation: The curved arrowsin the resonance structure mentioned below should be added.

  Organic Chemistry: A Guided Inquiry, Chapter 5, Problem 6E , additional homework tip  2

Concept introduction:When one single structure is unable to describe all the properties of single molecule, a phenomenon called resonance comes into play. This arises when two or more than two Lewis structures are possible for one molecule. All such structures are called resonating structures and have same placement of atoms in them but these have different locations of bond pairs and lone pairs. The resonating structures are inter-convertible with each other. The resultant of all the resonating or contributing structures is called the resonance hybrid.

Rules to form resonance structure are as follows:

1. Use arrow types 1 and 2 for resonance structure of anions in movement of negative charge. Arrow type 1 shows the movement of lone pair toward adjacent atom and then converted into π bond. Arrow type 2 shows the movement of π electron pair from double bond towards adjacent carbon and then converted into lone pair.

2. Use only arrow type 3 to move a positive charge for resonance structure of cations. Arrow type 3 is used to move π electron pair towards adjacent single bonds.

3. The sigma bond should not be broken. Any atom must not move from its place and total number of electrons must be same in all resonance structures.

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Students have asked these similar questions
A. Determine whether the curved arrow(s) shown below generate a valid or invalid resonance structure. Draw the resonance structure that would result from each properly drawn arrow and identify the arrow pushing pattern (i.e. allylic positive charge, allylic lone pair, pi bond between atoms of a different electronegativity, lone pair adjacent to a positive charge, alternating pi bonds in a ring.
2. Each resonance structure of a given molecule contributes to the resonance hybrid. The more stable the resonance structure, the more that resonance structure contributes to the resonance hybrid. For the following resonance structures, a. Circle the resonance structure that contributes most to the resonance hybrid. b. Explain your choice for a in complete sentences. c. Draw the resonance hybrid. d. Add curved arrows to indicate the flow of electrons in each structure except the D. H A Q Search B hyji C D
Draw a curved arrow starting from the t bond of Draw all atoms of the resulting resonance structure C. Show resonance structure B that will form resonance charges and lone pairs. structure C. Select Draw Rings More Erase Select Draw Rings More Erase C C H :0 : I. H Q Q Resonance structure C is a major (more important) resonance structure. minor (less important) resonance structure.

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Organic Chemistry: A Guided Inquiry

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ISBN:9780618974122
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