Grignard Synthesis: Ph-Mg-X + tert-Butyl Alcohol

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In summary, the conversation discusses the expected product and reaction mechanism of a reaction between Ph-Mg-X and tert-butyl alcohol. The expected product is tertbutyl benzene, while the actual product is benzene. The question also asks for an explanation of how this product is formed and for links to information about grignard reactions with alcohols.
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Homework Statement


Predict the product, along with the reaction mechanism,of the given reactants -:

[tex] Ph-Mg-X + tert-butyl alcohol \longrightarrow \ ? [/tex]

My attempt
This is a grignard synthesis, RMgX where R is phenyl carbanion . The general reaction with water gives alkanes,and X-Mg-OH . Similarly the reaction with alcohol should give tertbutyl benzene and X-Mg-OH ? But the given answer is benzene.
Could someone give an explanation as to how that is being formed ?
Any links to webpages explaining griganard reactions with alcohols will also be appreciated.
Thx
 
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What is the product of a reaction between a grignard (strong base and sometimes alkylating agent) and an alcohol?

This statement is not correct:
Similarly the reaction with alcohol should give tertbutyl benzene and X-Mg-OH ?
 
  • #3


I would like to clarify a few things about the given reaction. First, the product of this reaction is not simply benzene, but rather tert-butyl benzene. This is an important distinction because tert-butyl benzene is a specific compound with a unique structure, while benzene is a general term for a class of compounds with a six-carbon ring.

Now, let's look at the reaction mechanism. Grignard reagents, such as Ph-Mg-X, are highly reactive and can be thought of as a source of a carbanion (R-) in solution. In this reaction, the carbanion attacks the carbonyl group of the tert-butyl alcohol, leading to the formation of an intermediate alkoxide compound. This intermediate then undergoes protonation, resulting in the formation of tert-butyl benzene and Mg(OH)X. This is a common mechanism in Grignard reactions with alcohols.

If you are looking for more information on Grignard reactions with alcohols, I suggest checking out some organic chemistry textbooks or online resources. The mechanism and products of these reactions are well-studied and documented in the literature. Additionally, there are many videos and tutorials available online that can help you better understand this reaction.
 

What is Grignard Synthesis?

Grignard Synthesis is a chemical reaction that involves the use of a Grignard reagent, which is usually an alkyl- or aryl-magnesium halide (Ph-Mg-X), and a carbonyl compound, such as an aldehyde or ketone. This reaction creates a new carbon-carbon bond and is commonly used in organic synthesis.

What is the role of tert-Butyl Alcohol in Grignard Synthesis?

Tert-Butyl Alcohol (tBuOH) is used as a solvent in Grignard Synthesis. It helps to dissolve the reagents and reaction products and also stabilizes the Grignard reagent by coordinating with the magnesium atom.

What precautions should be taken when performing Grignard Synthesis?

Grignard reactions are highly reactive and can be dangerous if not performed properly. It is important to handle the reagents and products with caution, as they are highly flammable and can react violently with water. Additionally, the reactions should be performed in a well-ventilated area and protective gear, such as gloves and safety glasses, should be worn.

What are some common applications of Grignard Synthesis?

Grignard Synthesis is commonly used in organic chemistry to create new carbon-carbon bonds and synthesize complex organic molecules. It is also used in the production of pharmaceuticals, agrochemicals, and other industrial compounds.

What are some limitations of Grignard Synthesis?

Some limitations of Grignard Synthesis include the inability to form a Grignard reagent from compounds that contain acidic protons, such as alcohols and carboxylic acids. Additionally, the reaction may not proceed well with certain functional groups, such as nitro groups, which can react with the Grignard reagent instead of the carbonyl compound. Lastly, the reaction can be sensitive to impurities in the reagents, which can lead to side reactions or incomplete reactions.

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