What is the expected product of the given monobromination EAS reaction? (See p 316-317 if you haven't studied aromatic chemistry yet in CHEM 241B.) This aromatic ring is considered to be "activated" for electrophilic aromatic substitution. Draw resonance structures of acetanilide to determine if the NH- C(O)CH3 group is electron-donating or electron-withdrawing.
What is the expected product of the given monobromination EAS reaction? (See p 316-317 if you haven't studied aromatic chemistry yet in CHEM 241B.) This aromatic ring is considered to be "activated" for electrophilic aromatic substitution. Draw resonance structures of acetanilide to determine if the NH- C(O)CH3 group is electron-donating or electron-withdrawing.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
Related questions
Question
![●
●
Aromatic Bromination and Green Chemistry
Two step synthesis and identification of product
Will use vacuum filtration and analysis with m.p., IR, and NMR
Day 1: Protection of Aniline Nitrogen
(Amide Formation)
●
Modifying aniline through
reaction with acetic anhydride
Day 2: Aromatic Bromination
Monobromination of an activated
aromatic compound
Evaluation of directing effects by
the isomeric product obtained
Modification of procedure from Luong et al,
J. Chem Ed. 2012, 89, 1061-1063
NH₂
aniline
NH
NaBr, NaClO
AcOH, EtOH
acetanilide
para
NH
ΝΗ
Br
ortho
meta
Which position is brominated?
(ortho, meta, or para)](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F6484a2ba-7b6c-4144-bd9b-1f2d784a131b%2F0370e1b2-568d-4edc-b5a7-14b245e1307b%2Flueexzi_processed.jpeg&w=3840&q=75)
Transcribed Image Text:●
●
Aromatic Bromination and Green Chemistry
Two step synthesis and identification of product
Will use vacuum filtration and analysis with m.p., IR, and NMR
Day 1: Protection of Aniline Nitrogen
(Amide Formation)
●
Modifying aniline through
reaction with acetic anhydride
Day 2: Aromatic Bromination
Monobromination of an activated
aromatic compound
Evaluation of directing effects by
the isomeric product obtained
Modification of procedure from Luong et al,
J. Chem Ed. 2012, 89, 1061-1063
NH₂
aniline
NH
NaBr, NaClO
AcOH, EtOH
acetanilide
para
NH
ΝΗ
Br
ortho
meta
Which position is brominated?
(ortho, meta, or para)
![What is the expected product of the given monobromination EAS reaction? (See
p 316-317 if you haven't studied aromatic chemistry yet in CHEM 241B.)
This aromatic ring is considered to be "activated" for electrophilic aromatic
substitution. Draw resonance structures of acetanilide to determine if the NH-
C(O)CH3 group is electron-donating or electron-withdrawing.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F6484a2ba-7b6c-4144-bd9b-1f2d784a131b%2F0370e1b2-568d-4edc-b5a7-14b245e1307b%2F3xx2ws_processed.jpeg&w=3840&q=75)
Transcribed Image Text:What is the expected product of the given monobromination EAS reaction? (See
p 316-317 if you haven't studied aromatic chemistry yet in CHEM 241B.)
This aromatic ring is considered to be "activated" for electrophilic aromatic
substitution. Draw resonance structures of acetanilide to determine if the NH-
C(O)CH3 group is electron-donating or electron-withdrawing.
Expert Solution
![](/static/compass_v2/shared-icons/check-mark.png)
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 2 images
![Blurred answer](/static/compass_v2/solution-images/blurred-answer.jpg)
Knowledge Booster
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.Recommended textbooks for you
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9780078021558/9780078021558_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
![Chemistry: Principles and Reactions](https://www.bartleby.com/isbn_cover_images/9781305079373/9781305079373_smallCoverImage.gif)
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
![Elementary Principles of Chemical Processes, Bind…](https://www.bartleby.com/isbn_cover_images/9781118431221/9781118431221_smallCoverImage.gif)
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY