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Why monobromination of acetanilide occurs while tribromination o aniline would occur under the same conditions?
Monobromination of acetanilide occurs because the acetyl group (–C(=O)CH3) is an electron-withdrawing group that decreases the nucleophilicity of the aniline nitrogen, leading to selective bromination at the para position of the aromatic ring. In contrast, aniline has an amino group (–NH2), which is an electron-donating group that significantly increases the electron density on the aromatic ring, making it more reactive towards multiple bromination. Under the same conditions, the increased reactivity of aniline allows for tribromination to occur, as the ring can readily accommodate multiple bromine substitutions.
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monobromination of acetanilide occurs,while tribromination of aniline would occur under the same conditions?
Write a detailed set of equations for the acetylation reaction, and in particular show clearly that the reaction can be regarded as a nucleophilic substitution, in which the attacking nucleophile is aniline (attacking acetic anhydride).
Is acetanilide an amide?
Yes, acetanilide is an amide. It is derived from aniline and acetic acid, containing the amide functional group (-CONH2).
What is the alternative route of synthesis of acetanilide?
Acetanilide can also be synthesized by reacting aniline with acetic anhydride, instead of acetyl chloride. This is known as the Acetic Anhydride Method.
Why is acetanilide nitrated and not aniline?
Acetanilide is nitrated instead of aniline because the acetyl group in acetanilide exhibits electron-withdrawing properties that stabilize the intermediate formed during nitration. This leads to a more controlled reaction and reduces the likelihood of over-nitration, which can occur with aniline due to its strong activating amino group. Additionally, the presence of the acetyl group decreases the nucleophilicity of the amine, promoting a more selective nitration.
What reagents may be used for the preparation of acetanilide?
Acetanilide can be prepared using aniline and acetic anhydride as reagents. The reaction typically requires the presence of a catalyst, such as zinc chloride, to facilitate the acetylation of aniline to form acetanilide. The reaction is usually carried out in the presence of a base, like sodium acetate, to neutralize the acidic byproduct formed during the reaction.
monobromination of acetanilide occurs,while tribromination of aniline would occur under the same conditions?
Write a detailed set of equations for the acetylation reaction, and in particular show clearly that the reaction can be regarded as a nucleophilic substitution, in which the attacking nucleophile is aniline (attacking acetic anhydride).
Why do you use acetanilide rather aniline in the synthesis of p-nitroaniline?
Acetanilide is used instead of aniline in the synthesis of p-nitroaniline to control the selectivity of the reaction. Acetanilide is less reactive than aniline, making it easier to control the nitration process and avoid the formation of unwanted byproducts. Additionally, the acetanilide group can be easily removed after the nitration reaction to yield p-nitroaniline.
Is acetanilide an amide?
Yes, acetanilide is an amide. It is derived from aniline and acetic acid, containing the amide functional group (-CONH2).
What is an acetanilid?
An acetanilide is an amide derived from acetic acid and aniline, once used as an analgesic and antipyretic.
What is the alternative route of synthesis of acetanilide?
Acetanilide can also be synthesized by reacting aniline with acetic anhydride, instead of acetyl chloride. This is known as the Acetic Anhydride Method.
Why is acetanilide nitrated and not aniline?
Acetanilide is nitrated instead of aniline because the acetyl group in acetanilide exhibits electron-withdrawing properties that stabilize the intermediate formed during nitration. This leads to a more controlled reaction and reduces the likelihood of over-nitration, which can occur with aniline due to its strong activating amino group. Additionally, the presence of the acetyl group decreases the nucleophilicity of the amine, promoting a more selective nitration.
What reagents may be used for the preparation of acetanilide?
Acetanilide can be prepared using aniline and acetic anhydride as reagents. The reaction typically requires the presence of a catalyst, such as zinc chloride, to facilitate the acetylation of aniline to form acetanilide. The reaction is usually carried out in the presence of a base, like sodium acetate, to neutralize the acidic byproduct formed during the reaction.
Why add of little amount from acetic anhydride in synthesis of acetanilide?
Adding a small amount of acetic anhydride helps to facilitate the acetylation reaction with aniline, leading to the formation of acetanilide. The acetic anhydride serves as an acetylating agent that transfers an acetyl group to the amine group of aniline, resulting in the desired product. The use of an excess of acetic anhydride is avoided to prevent side reactions and to optimize the yield of acetanilide.
Why is there only one acyl group placed on aniline in the reaction forming acetanilide?
Actually it is possible to put a second acyl group on as well, for example with acetyl chloride and triethylamine. Under aqueous basic conditions the second acyl group is far more readily hydrolysed.
Among benzyl amine aniline acetanilide and p-nitro aniline which is the most basic compound?
Among the compounds listed, aniline is the most basic as it has a lone pair on the nitrogen atom that can readily accept a proton. Benzylamine and p-nitroaniline are less basic due to the presence of electron-withdrawing groups, while acetanilide has a resonance-stabilized amide group that reduces its basicity.
What is the reagent catalyst and solvent from aniline to acetanilide?
To convert aniline to acetanilide, the reagent used is acetic anhydride or acetyl chloride. The reaction typically requires a catalyst such as a base, like pyridine, to facilitate the acetylation. The solvent can be a non-polar organic solvent like dichloromethane or toluene, although the reaction can also proceed without a solvent.
What is the role of the acetic anhydride in this reaction in the synthesis of acetanilide?
Acetic anhydride acts as an acetylating agent, adding an acetyl group to the amine group of aniline to form acetanilide. The acetyl group adds functionality to the aniline molecule, making it less basic and more soluble in organic solvents.
