Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
bartleby

Concept explainers

Question
Book Icon
Chapter 22, Problem 22.14P

(a)

Interpretation Introduction

Interpretation:

Resonance contributor for the cation formed during electrophilic aromatic substitution has to be given for the given ortho-para directing -OH group.

Concept Introduction:

Activating and deactivating groups:

The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.

Activating groups – ortho/para directing groups.  The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.

Deactivating groups – meta directing groups.  The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.

(b)

Interpretation Introduction

Interpretation:

Resonance contributor for the cation formed during electrophilic aromatic substitution has to be given for the given ortho-para directing -OC(O)CH3 group.

Concept Introduction:

Activating and deactivating groups:

The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.

Activating groups – ortho/para directing groups.  The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.

Deactivating groups – meta directing groups.  The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.

(c)

Interpretation Introduction

Interpretation:

Resonance contributor for the cation formed during electrophilic aromatic substitution has to be given for the given ortho-para directing -N(CH3)2 group.

Concept Introduction:

Activating and deactivating groups:

The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.

Activating groups – ortho/para directing groups.  The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.

Deactivating groups – meta directing groups.  The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.

(d)

Interpretation Introduction

Interpretation:

Resonance contributor for the cation formed during electrophilic aromatic substitution has to be given for the given ortho-para directing -NHC(O)CH3 group.

Concept Introduction:

Activating and deactivating groups:

The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.

Activating groups – ortho/para directing groups.  The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.

Deactivating groups – meta directing groups.  The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.

(e)

Interpretation Introduction

Interpretation:

Resonance contributor for the cation formed during electrophilic aromatic substitution has to be given for the given ortho-para directing phenyl group.

Concept Introduction:

Activating and deactivating groups:

The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.

Activating groups – ortho/para directing groups.  The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.

Deactivating groups – meta directing groups.  The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.

Blurred answer
Students have asked these similar questions
In the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?
a. Compound X is benzene, Y is acetic anhydride acid. Complete the following scheme and determine Z! b. Determine which reagents except acetic acid anhydrides can replace Y!
8a)Provide mechanisms for the following reactions:

Chapter 22 Solutions

Organic Chemistry

Ch. 22 - What product do you predict from the reaction of...Ch. 22 - Other groups besides H+ can act as leaving groups...Ch. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Suggest a reason why the nitroso group, N=O, is...Ch. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - The following molecules each contain two aromatic...Ch. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - The insecticide DDT is prepared by the following...Ch. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.32PCh. 22 - Show how to prepare each compound from...Ch. 22 - Prob. 22.34PCh. 22 - Show reagents and conditions to bring about the...Ch. 22 - Prob. 22.36PCh. 22 - Propose a synthesis for each compound from...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Cancer of the prostate is the second leading cause...Ch. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - When certain aromatic compounds are treated with...Ch. 22 - Prob. 22.49PCh. 22 - Following is the structure of miconazole, the...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Show how the antidepressant venlafaxine (Effexor)...Ch. 22 - Prob. 22.57PCh. 22 - Given this retrosynthetic analysis, propose a...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - A newer generation of antipsychotics, among them...Ch. 22 - Prob. 22.63P
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning