Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 15, Problem 1PP

PRACTICE PROBLEM 15.1

Show how loss of a proton can be represented using each of the three resonance structures for the arenium ion and show how each representation leads to the formation of a benzene ring with three alternating double bonds (i.e., six fully delocalized π electrons).

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Interpretation Introduction

Interpretation:

The loss of protons from three resonating structures of the areniumion, are to be shown.

Concept Introduction:

Arrows present in the mechanism of the reaction indicate the electron transfer, starting from negatively charged species and ending at the positively charged species.

Electrophiles attract negatively charged species and nucleophiles attract positively charged species.

Answer to Problem 1PP

Solution: The loss of protons from the three resonating structures of the arenium ion are shown as follows:

Organic Chemistry, Chapter 15, Problem 1PP , additional homework tip  1

Explanation of Solution

The resonating structures of the arenium ion, formed in the electrophilic substitution reaction of benzene, are shown below:

Organic Chemistry, Chapter 15, Problem 1PP , additional homework tip  2

The removal of proton occurs from the carbon atom where the electrophile is attached and the bond pairs of electrons of CH bond get transferred to the ring, resulting in the formation of three double bonds, which implies that the aromaticity is regained.

The removal of proton from (I) resonating structure is shown as follows:

Organic Chemistry, Chapter 15, Problem 1PP , additional homework tip  3

The removal of proton from (II) resonating structure is shown as follows:

Organic Chemistry, Chapter 15, Problem 1PP , additional homework tip  4

The removal of proton from (III) resonating structure is shown as follows:

Organic Chemistry, Chapter 15, Problem 1PP , additional homework tip  5

Conclusion

The removal of protons from the arenium ion leads to the transfer of bond pairs to the benzene ring and the delocalization of these electrons on the ring occurs, to form the final product.

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Chapter 15 Solutions

Organic Chemistry

Ch. 15 - PRACTICE PROBLEM 15.11 Predict the major products...Ch. 15 - PRACTICE PROBLEM 15.12 Predict the major product...Ch. 15 - PRACTICE PROBLEM 15.13 Write mechanisms for the...Ch. 15 - Prob. 14PPCh. 15 - PRACTICE PROBLEM 15.15 Suppose you needed to...Ch. 15 - PRACTICE PROBLEM 15.16 1-Fluoro-2,4-dinitrobenzene...Ch. 15 - Prob. 17PPCh. 15 - PRACTICE PROBLEM 15.18 When...Ch. 15 - PRACTICE PROBLEM 15.19 Birch reduction of toluene...Ch. 15 - Prob. 20PCh. 15 - Prob. 21PCh. 15 - What monobromination product (or products) would...Ch. 15 - 15.23 Predict the major products of the following...Ch. 15 - Prob. 24PCh. 15 - 15.25 Starting with styrene, outline a synthesis...Ch. 15 - Prob. 26PCh. 15 - 15.27 Starting with aniline, outline a synthesis...Ch. 15 - Prob. 28PCh. 15 - Propose structures for compounds GI:Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - Prob. 31PCh. 15 - 15.32 Give structures (including stereochemistry...Ch. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 35PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 37PCh. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - Predict the product of the following reaction.Ch. 15 - 15.42 When m-chlorotoluene is treated with sodium...Ch. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - 15.47 Provide structures for compounds A and B: Ch. 15 - Prob. 48PCh. 15 - 15.49 Treating cyclohexene with acetyl chloride...Ch. 15 - 15.50 The tert-butyl group can be used as a...Ch. 15 - 15.51 When toluene is sulfonated (concentrated )...Ch. 15 - Prob. 52PCh. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - A C-D bond is harder to break than a C-H bond,...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - When compound C, which is often used to model a...Ch. 15 - Open the molecular model file for benzyne and...Ch. 15 - The structure of thyroxine, a thyroid hormone that...Ch. 15 - Prob. 2LGPCh. 15 - 3. Deduce the structures of compounds E–L in the...
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