Organometallic Reaction: Benzoic Acid and Phenylmagnesium Bromide Equation

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In summary, the conversation discusses the reaction between benzoic acid and phenylmagnesium bromide. The question asks for an equation showing this reaction, and the conversation mentions the use of Grignard reagents in organic chemistry and their lack of use in this specific reaction.
  • #1
Sastronaut
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Homework Statement


Write an equation showing how benzoic acid would react with phenylmagnesium bromide.

Homework Equations

The Attempt at a Solution


I am not quite sure where to start first with this Reaction. I haven't seen a Organometallic + acid reaction before. I realize that i have an acidic hydrogen but what would be the first step? would an ether result!? any help would be greatly appreciated, thanks pf! :)
 
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  • #2
Magnesium and bromide in organic chemistry means only one type of reaction. Actually just googling for reactions of phenylmagnesium bromide gives name of the reaction between first hits. You should really try harder before asking.
 
  • #3
I know borek, thank you. It gives you the (preparation) reaction mechanism to form phenyl magnesium bromide from bromobenzene and magnesium metal which i understand. It also shows the mechanism to form triphenylmethonal with phenyl magnesium bromide which i also understand. But neither of those reactions use benzoic acid and that is what is throwing me off
 
  • #4
Phenyl magnesium bromide is a Grignard reagent - have you heard that name?

What is a common use of Grignard reagents?

Why is it of no use here?
 
  • #5


The reaction between benzoic acid and phenylmagnesium bromide is known as a Grignard reaction. The equation for this reaction is:

C6H5COOH + C6H5MgBr → C6H5COOMgBr + C6H6

In this reaction, the phenylmagnesium bromide acts as a nucleophile, attacking the carbonyl carbon in benzoic acid. This results in the formation of a new carbon-carbon bond, and the formation of a magnesium salt (C6H5COOMgBr). The resulting product is then protonated with water or acid to form the final product, benzene (C6H6).

The first step in this reaction is the formation of the Grignard reagent, phenylmagnesium bromide, by reacting magnesium metal with phenylbromide in an ether solvent. This is then followed by the addition of benzoic acid to the Grignard reagent, resulting in the formation of the final product.

Overall, this reaction is a useful method for the synthesis of substituted benzenes, and has many applications in organic synthesis.
 

1. What are organometallic reactions?

Organometallic reactions are chemical reactions that involve the transfer or exchange of a carbon-containing group (known as an organometallic compound) with a metal atom or ion. These reactions are important in both organic and inorganic chemistry and are widely used in the synthesis of complex molecules and materials.

2. How do organometallic reactions differ from other types of reactions?

Organometallic reactions involve the direct interaction between a metal atom or ion and a carbon-containing compound, whereas other types of reactions typically involve the transfer of electrons between atoms. Additionally, organometallic reactions often proceed through a stepwise mechanism, involving the formation and breakdown of intermediates, rather than a single-step process.

3. What are some common applications of organometallic reactions?

Organometallic reactions are widely used in organic synthesis to form new carbon-carbon and carbon-heteroatom bonds, as well as in the production of pharmaceuticals, agrochemicals, and other industrial products. They are also important in catalysis, where metal complexes are used to facilitate and control chemical reactions.

4. Can organometallic reactions occur with any metal?

Yes, organometallic reactions can occur with a wide variety of metals, including transition metals, main group metals, and lanthanides and actinides. The choice of metal often depends on the specific reaction conditions and the desired product.

5. What are some challenges associated with organometallic reactions?

Organometallic reactions can be sensitive to air and moisture, and many require specialized equipment and techniques to carry out. Additionally, the reactivity and selectivity of these reactions can be difficult to predict, making it important for chemists to carefully design and optimize their reactions to achieve the desired outcome.

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