Organic Chemistry, Loose-leaf Version
Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 21, Problem 21.13P

(a)

Interpretation Introduction

Interpretation: As a hybrid of five contributing structures the given molecule has to be drawn.

Concept Introduction:

Kekule structures:

The double bonds of an aromatic ring shift back and forth very rapidly. The resulted forms or structures cannot be separated and stay in equilibrium. Those structures are known as Kekule structures.

The Kekule structure for benzene ring:

Organic Chemistry, Loose-leaf Version, Chapter 21, Problem 21.13P , additional homework tip  1

The back and forth shift of the double bonds in between these two forms is shown here:

Organic Chemistry, Loose-leaf Version, Chapter 21, Problem 21.13P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation: As a hybrid of five contributing structures the given molecule has to be drawn.

Concept Introduction:

Kekule structures:

The double bonds of an aromatic ring shift back and forth very rapidly. The resulted forms or structures cannot be separated and stay in equilibrium. Those structures are known as Kekule structures.

The Kekule structure for benzene ring:

Organic Chemistry, Loose-leaf Version, Chapter 21, Problem 21.13P , additional homework tip  3

The back and forth shift of the double bonds in between these two forms is shown here:

Organic Chemistry, Loose-leaf Version, Chapter 21, Problem 21.13P , additional homework tip  4

(c)

Interpretation Introduction

Interpretation: As a hybrid of five contributing structures the given molecule has to be drawn.

Concept Introduction:

Kekule structures:

The double bonds of an aromatic ring shift back and forth very rapidly. The resulted forms or structures cannot be separated and stay in equilibrium. Those structures are known as Kekule structures.

The Kekule structure for benzene ring:

Organic Chemistry, Loose-leaf Version, Chapter 21, Problem 21.13P , additional homework tip  5

The back and forth shift of the double bonds in between these two forms is shown here:

Organic Chemistry, Loose-leaf Version, Chapter 21, Problem 21.13P , additional homework tip  6

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Chapter 21 Solutions

Organic Chemistry, Loose-leaf Version

Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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