Organic Chemistry, Books a la Carte Edition (8th Edition)
Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 18, Problem 50P

a)

Interpretation Introduction

Interpretation:

The most reactive compound in an electrophilic aromatic substitution reaction for each row of substituted benzenes has to be predicted.

Concept Introduction:

Effect of an electron withdrawing or an electron releasing group:

The electron withdrawing or electron releasing groups have significance role in the activation and deactivation of benzene rings during an electrophilic aromatic substitution reaction. An electron withdrawing group deactivates the benzene rings by reducing the electron density on the rings. The electrophilic groups have the tendency to accept or withdraw the electrons from the rest of compound. The deactivating groups are those groups that tend to withdraw the electron density from the benzene ring and decrease the overall rate of reactions.

Rule: The rate of reactions in aromatic electrophilic substitution reactions rely upon the presence of an electron releasing or an electron withdrawing group.

b)

Interpretation Introduction

Interpretation:

The least reactive compound in an electrophilic aromatic substitution reaction for each row of substituted benzenes has to be predicted.

Concept Introduction:

Effect of an electron withdrawing or an electron releasing group:

The electron withdrawing or electron releasing groups have significance role in the activation and deactivation of benzene rings during an electrophilic aromatic substitution reaction. An electron withdrawing group deactivates the benzene rings by reducing the electron density on the rings. The electrophilic groups have the tendency to accept or withdraw the electrons from the rest of compound. The deactivating groups are those groups that tend to withdraw the electron density from the benzene ring and decrease the overall rate of reactions.

Rule: The rate of reactions in aromatic electrophilic substitution reactions rely upon the presence of an electron releasing or an electron withdrawing group.

c)

Interpretation Introduction

Interpretation:

The compound that yields the highest percentage of a meta product in an electrophilic aromatic substitution reaction for each horizontal row of substituted benzenes has to be stated.

Concept Introduction:

Effect of an electron withdrawing or an electron releasing group:

The electron withdrawing or electron releasing groups have significance role in the activation and deactivation of benzene rings during an electrophilic aromatic substitution reaction. An electron withdrawing group deactivates the benzene rings by reducing the electron density on the rings. The electrophilic groups have the tendency to accept or withdraw the electrons from the rest of compound. The deactivating groups are those groups that tend to withdraw the electron density from the benzene ring and decrease the overall rate of reactions.

Rule: The rate of reactions in aromatic electrophilic substitution reactions rely upon the presence of an electron releasing or an electron withdrawing group.

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For each horizontal row of substituted benzenes, indicate a. the one that is the most reactive in an electrophilic aromatic substitution reaction. b. the one that is the least reactive in an electrophilic aromatic substitution reaction. c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.
For each horizontal row of substituted benzenes, indicatea. the one that is the most reactive in an electrophilic aromatic substitution reaction.b. the one that is the least reactive in an electrophilic aromatic substitution reaction.c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.
Draw all secondary resonance structures for benzaldehyde. a. Is the aldehyde group electron donating or electron withdrawing? b. Which position(s) on the aromatic ring are most likely to react with an electrophile? H

Chapter 18 Solutions

Organic Chemistry, Books a la Carte Edition (8th Edition)

Ch. 18.12 - Prob. 14PCh. 18.12 - List the compounds in each set from most reactive...Ch. 18.13 - Prob. 16PCh. 18.13 - What product(s) result from nitration of each of...Ch. 18.13 - Prob. 18PCh. 18.13 - What products are obtained from the reaction of...Ch. 18.15 - Give the products, if any, of each of the...Ch. 18.16 - a. Does a coupling reaction have to be used to...Ch. 18.16 - Show how the following compounds can be...Ch. 18.16 - Prob. 24PCh. 18.17 - What is the major product(s) of each of the...Ch. 18.17 - Prob. 26PCh. 18.18 - Why isn't FeBr3 used as a catalyst in the first...Ch. 18.18 - Prob. 29PCh. 18.18 - Write the sequence of steps required for the...Ch. 18.18 - Show how the following compounds can be...Ch. 18.19 - What product is formed from reaction of...Ch. 18.19 - Prob. 33PCh. 18.19 - Draw the structure of the activated ring and the...Ch. 18.20 - Prob. 35PCh. 18.20 - Prob. 36PCh. 18.20 - Diazomethane can be used to convert a carboxylic...Ch. 18.21 - Prob. 38PCh. 18.21 - Prob. 39PCh. 18.21 - Prob. 40PCh. 18.22 - Prob. 41PCh. 18 - Draw the structure for each of the following: a....Ch. 18 - Name the following:Ch. 18 - Prob. 44PCh. 18 - Prob. 45PCh. 18 - For each of the statements in Column I, choose a...Ch. 18 - What product is obtained from the reaction of...Ch. 18 - Draw the product(s) of each of the following...Ch. 18 - Rank the following substituted anilines from most...Ch. 18 - Prob. 50PCh. 18 - Prob. 51PCh. 18 - Show how the following compounds can be...Ch. 18 - Prob. 53PCh. 18 - The compound with the 1H NMR spectrum shown below...Ch. 18 - Rank each group of compounds from most reactive to...Ch. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - For each of the following components, indicate the...Ch. 18 - Prob. 59PCh. 18 - Prob. 60PCh. 18 - Describe two ways to prepare anisole from benzene.Ch. 18 - Prob. 62PCh. 18 - The following tertiary alkyl bromides undergo an...Ch. 18 - An aromatic hydrocarbon with a molecular formula...Ch. 18 - Show how the following compounds can be...Ch. 18 - Use the four compounds shown below to answer the...Ch. 18 - a. Rank the following esters from most reactive to...Ch. 18 - A mixture of 0.10 mol benzene and 0.10 mol...Ch. 18 - Prob. 69PCh. 18 - Prob. 70PCh. 18 - Benzene underwent a Friedel-Crafts acylation...Ch. 18 - Prob. 72PCh. 18 - Prob. 73PCh. 18 - Friedel-Crafts alkylations can be carried out with...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 76PCh. 18 - Prob. 77PCh. 18 - a. Describe four ways the following reaction can...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - How can you prepare the following compounds with...Ch. 18 - Describe how naphthalene can he prepared from the...Ch. 18 - Using resonance contributors for the carbocation...Ch. 18 - Prob. 83PCh. 18 - What reagents are required to carry out the...Ch. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Prob. 87PCh. 18 - Propose a mechanism for each of the following...Ch. 18 - P-Fluoronitrobenzene is more reactive toward...Ch. 18 - When heated with chromic acid, compound A forms...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - How can you distinguish the following compounds...Ch. 18 - Describe how mescaline can be synthesized from...Ch. 18 - Propose a mechanism for the following reaction...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - Describe how 3-methyl-1-phenyl-3-pentanol can he...Ch. 18 - An unknown compound reacts with ethyl chloride and...Ch. 18 - a. Explain why the following reaction leads to the...Ch. 18 - Explain why hydroxide ion catalyzes the reaction...Ch. 18 - Prob. 100PCh. 18 - Prob. 101PCh. 18 - a. How can aspirin be synthesized from benzene? b....Ch. 18 - Prob. 103PCh. 18 - Show how Novocain, a painkiller used frequently by...Ch. 18 - Prob. 105PCh. 18 - Saccharin, an artificial sweetener, is about 300...
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