Homework Help is Here – Start Your Trial Now!
Science
Chemistry
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
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...
See similar textbooks
icon
Related questions
Question

Draw the reaction scheme. Use one arrow direct from starting materials to products.

**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. ### Diagram: 1. **Step 1: Formation of phenyl magnesium bromide** - A bromobenzene reacts with magnesium metal in diethyl ether at 35°C to form phenyl magnesium bromide (Grignard reagent). ![Step 1 Reaction](https://via.placeholder.com/500) 2. **Step 2: Formation of benzoic acid** - The phenyl magnesium bromide reacts with solid carbon dioxide, followed by hydrolysis with water, to form benzoic acid. ![Step 2 Reaction](https://via.placeholder.com/500) **Potential Side Reaction:** 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. - Biphenyl formation occurs when two phenyl magnesium bromide molecules react to form biphenyl and magnesium bromide. ![Side Reaction](https://via.placeholder.com/500) --- **Note:** Ensure the reaction setup protects reagents from moisture and conducts reactions under controlled conditions to minimize side reactions.
Transcribed Image Text:**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. ### Diagram: 1. **Step 1: Formation of phenyl magnesium bromide** - A bromobenzene reacts with magnesium metal in diethyl ether at 35°C to form phenyl magnesium bromide (Grignard reagent). ![Step 1 Reaction](https://via.placeholder.com/500) 2. **Step 2: Formation of benzoic acid** - The phenyl magnesium bromide reacts with solid carbon dioxide, followed by hydrolysis with water, to form benzoic acid. ![Step 2 Reaction](https://via.placeholder.com/500) **Potential Side Reaction:** 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. - Biphenyl formation occurs when two phenyl magnesium bromide molecules react to form biphenyl and magnesium bromide. ![Side Reaction](https://via.placeholder.com/500) --- **Note:** Ensure the reaction setup protects reagents from moisture and conducts reactions under controlled conditions to minimize side reactions.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Carboxylic Acids and their Derivatives
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
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY
SEE MORE TEXTBOOKS