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

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.69P

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