INTRODUCTION: Preparation of Benzoic Acid In organometallic compounds, such as Grignard reagents, the carbon directly attached to the metal has the nature of a carbanion. Organometallic compounds behave as strong bases and, as expected, they react with acids to form a C- H bond. On the other hand, organometallic compounds also react as good nucleophiles especially in addition reactions to compounds with carbonyl groups to form secondary or tertiary alcohols. Since organometallic compounds are also able to react with oxygen, and water in the air, it is important to protect them from air and moisture when they are used or stored. Today, you will synthesize a Grignard reagent (phenyl magnesium bromide) and then use that Grignard reagent in a reaction with carbon dioxide to form the desired product, benzoic acid. Notice in the procedure that we are never isolating the Grignard reagent; we must observe its presence before continuing to the second step of the synthesis. Br Mg metal MgBr MgBr .COOH 1) CO, (solid) diethyl ether 35 °C 2) H,0 Step 1: Formation of phenyt magnesium bromide Step 2: Formation of benzoic acid
INTRODUCTION: Preparation of Benzoic Acid In organometallic compounds, such as Grignard reagents, the carbon directly attached to the metal has the nature of a carbanion. Organometallic compounds behave as strong bases and, as expected, they react with acids to form a C- H bond. On the other hand, organometallic compounds also react as good nucleophiles especially in addition reactions to compounds with carbonyl groups to form secondary or tertiary alcohols. Since organometallic compounds are also able to react with oxygen, and water in the air, it is important to protect them from air and moisture when they are used or stored. Today, you will synthesize a Grignard reagent (phenyl magnesium bromide) and then use that Grignard reagent in a reaction with carbon dioxide to form the desired product, benzoic acid. Notice in the procedure that we are never isolating the Grignard reagent; we must observe its presence before continuing to the second step of the synthesis. Br Mg metal MgBr MgBr .COOH 1) CO, (solid) diethyl ether 35 °C 2) H,0 Step 1: Formation of phenyt magnesium bromide Step 2: Formation of benzoic acid
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
Draw the reaction scheme. Use one arrow direct from starting materials to products.
![INTRODUCTION: Yreparation of Benzoic Acid
In organometallic compounds, such as Grignard reagents, the carbon directly attached to the metal has the nature of
a carbanion. Organometallic compounds behave as strong bases and, as expected, they react with acids to form a C-
H bond. On the other hand, organometallic compounds also react as good nucleophiles especially in addition
reactions to compounds with carbonyl groups to form secondary or tertiary alcohols. Since organometallic
compounds are also able to react with oxygen, and water in the air, it is important to protect them from air and
moisture when they are used or stored.
Today, you will synthesize a Grignard reagent (phenyl magnesium bromide) and then use that Grignard reagent in a
reaction with carbon dioxide to form the desired product, benzoic acid. Notice in the procedure that we are never
isolating the Grignard reagent; we must observe its presence before continuing to the second step of the synthesis.
MgBr
.COOH
MgBr
1) CO, (solid)
Br
Mg metal
2) H,0'
diethyl ether
35°C
Step 2: Formation of benzoic acid
Step 1: Formation of phenyl magnesium bromide
Due to the possible formation of side products such as biphenyl, the reaction has to be done at a well-controlled
temperature. If any formation of biphenyl occurs, it can be separated from the desired product during the extraction
step.
MgBr
Br
+ MgBr2
biphenyl
brobenzene Ke
Potential side reaction](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F0c9cc737-bc69-4364-ac27-de0ca112dbcd%2F7cfef90e-b5dc-4541-b402-53f436d08116%2Fi9bs009_processed.jpeg&w=3840&q=75)
Transcribed Image Text:INTRODUCTION: Yreparation of Benzoic Acid
In organometallic compounds, such as Grignard reagents, the carbon directly attached to the metal has the nature of
a carbanion. Organometallic compounds behave as strong bases and, as expected, they react with acids to form a C-
H bond. On the other hand, organometallic compounds also react as good nucleophiles especially in addition
reactions to compounds with carbonyl groups to form secondary or tertiary alcohols. Since organometallic
compounds are also able to react with oxygen, and water in the air, it is important to protect them from air and
moisture when they are used or stored.
Today, you will synthesize a Grignard reagent (phenyl magnesium bromide) and then use that Grignard reagent in a
reaction with carbon dioxide to form the desired product, benzoic acid. Notice in the procedure that we are never
isolating the Grignard reagent; we must observe its presence before continuing to the second step of the synthesis.
MgBr
.COOH
MgBr
1) CO, (solid)
Br
Mg metal
2) H,0'
diethyl ether
35°C
Step 2: Formation of benzoic acid
Step 1: Formation of phenyl magnesium bromide
Due to the possible formation of side products such as biphenyl, the reaction has to be done at a well-controlled
temperature. If any formation of biphenyl occurs, it can be separated from the desired product during the extraction
step.
MgBr
Br
+ MgBr2
biphenyl
brobenzene Ke
Potential side reaction
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