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 26CTQ

(a)

Interpretation Introduction

Interpretation: Categorization of resonance structures as “Equivalent” and “Not equivalent” resonance structure for the bases mentioned below should be determined.

  Organic Chemistry: A Guided Inquiry, Chapter 5, Problem 26CTQ , 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.

(b)

Interpretation Introduction

Interpretation: Resonance structure in base mentioned below that has lowest potential energy should be determined.

  Organic Chemistry: A Guided Inquiry, Chapter 5, Problem 26CTQ , 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.

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Be sure to answer all parts. The pk of three different C-H bonds is given below. For each compound, draw the conjugate base, including all possible resonance structures for compound C. Use skeletal structures when drawing all conjugate bases. compound A H H H pK₂ = 50 Conjugate base of compound A: Conjugate base of compound B: Conjugate base of compound C: edit structure ... compound B resonance structure (negative charge on C) H H edit structure ... (one Lewis structure) edit structure ... (one resonance structure) X H pka = 43 compound C edit structure ... H H pK₂ = 19.2 resonance structure (negative charge on O) H
13. Aniline and nitrobenzene are two substituted benzene compounds that contain nitrogen atoms. A) Use resonance structures to identify all carbon atoms that are electron rich on aniline. Mark the appropriate carbons in the figure below with a d-. NH₂ nitrobenzene aniline Note: this is benzene B) Use resonance structures to identify all carbon atoms that are electron deficient on nitrobenzene. Mark the appropriate carbons in the figure below with a dª.
O REPRESENTATIONS OF ORGANIC MOLECULES Ranking resonance structures Rank the resonance structures in each row of the table from major to minor. For example, in the first row, select (major) for the major resonance contributor. If two or more structures in the same row contribute equally, rank them equally by selecting the same number. H. H H. H. H. H. H. H. (Rank) (Rank) (Rank) H. H. H. H. H. H. H. (Rank) (Rank) :o: Rank) (Rank) 74°F DELL F5 F6 F7 F8 F9 F10 F11 PrtScr F12 24

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Organic Chemistry: A Guided Inquiry

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Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning