What is the mechanism for nitration of methyl benzoate?
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What is the mechanism for nitration of methyl benzoate?
The nitration of methyl benzoate is an example of electrophilic substitution. The carbonyl group withdraws electron density from the ring deactivating it towards electrophilic substitution.
What is the role of sulfuric acid in the nitration of methyl benzoate with nitric acid?
Nitric and sulfuric acid react to form the nitronium ion electrophile. Nucleophilic π electrons attack the nitronium ion giving methyl 3-nitrobenzoate.
Why does methyl benzoate dissolve in sulfuric acid?
Answer and Explanation: Concentrated sulfuric acid converts methyl benzoate into benzoic acid. Therefore, the polar benzoic acid dissolves in polar sulfuric acid. Therefore, methyl benzoate is soluble in sulfuric acid.
Why does nitration of methyl benzoate follow an electrophilic aromatic substitution mechanism instead of a simple addition across a double bond mechanism?
In contrast to the double bonds causing the unsaturation of benzene, it is strong and unreactive because of its resonance structure where there is rearrangement of electron pair. They undergo EAS or Electrophilic Aromatic Substitution reaction due to the fact that they are electron rich.
What is the role of conc h2so4 in nitration reaction of benzene?
In the protonation of nitric acid by sulfuric acid, the source of the nitronium ion induces the removal of a water molecule and the creation of a nitronium ion. The first step in benzene nitration is to activate HNO3 with sulfuric acid to create a nitronium ion, a stronger electrophile.
What is the use of sulphuric acid in nitration process?
Nitration Reaction The sulfuric acid is used as dehydration agent and promotes the formation of reactive nitronium ions (Eq. 1). The nitration as addition of the nitronium ion to the aromatic compound occurs in the aqueous acid phase.
What type of reaction was the nitration of methyl benzoate and what is the key intermediate formed?
The solvent of the nitration which is the sulfuric acid will protonate the reagent, methyl benzoate, which will create stabilized carbocation intermediate. The electrophile or the electron poor nitronium ion, will react to the protonated intermediate in the meta position.
How does electrophilic aromatic substitution work?
Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile.
Why is sulfuric acid used in aromatic nitration?
Sulfuric acid is needed in order for a good electrophile to form. Sulfuric acid protonates nitric acid to form the nitronium ion (water molecule is lost). The nitronium ion is a very good electrophile and is open to attack by benzene. Without sulfuric acid the reaction would not occur.
What is methyl benzoate soluble in?
Methyl benzoate is an organic compound. It is an ester with the chemical formula C6H5CO2CH3. It is a colorless liquid that is poorly soluble in water, but miscible with organic solvents….CHEBI:72775.
| Synonyms | Sources |
|---|---|
| Benzoic acid, methyl ester | ChemIDplus |
| Methyl benzenecarboxylate | ChemIDplus |
| methyl benzoate | UniProt |
Why h2so4 is used in nitration?
Why does nitration occur at the meta position of methyl benzoate instead of the ortho and para position?
Due to the presence of an electron-withdrawing group that is ester group ( -COOCH3 ) on methyl benzoate, the electron density at ortho and para position is less and incoming electrophile will attack position where the electron density is high that is at the meta position.
What is the role of h2so4 in nitration process?
What is the role of HNO3 in nitration reaction?
HNO3 acts as a base in the nitrating mixture and provides the electrophile NO2+ .
