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The -NHCOR group is less powerfully activating then the -NH2 group. In addition, the degree of steric hindrance is much greater in the case of a -NHCOR group, such as is found in acetanilide. This results in the compound being much more para directing. For an example, see Morrison and Boyd 's text "Organic Chemistry", sixth edition, Page 848.

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Why acetanilide brominates in the ortho and para positions and the amount of o-bromoacetanilide?

Acetanilide undergoes bromination in the ortho and para positions due to the presence of the activating amino group that directs the electrophilic bromine to these positions. In the reaction mixture, the para-bromoacetanilide is the major product compared to the ortho isomer, typically in a ratio of about 4:1.


Why is only 4-bromoacetanilide created mainly from a bromination of acetanilide?

The Acetanilide is a benzene with a acetamido group attached to it. The acetamido group is electron donating and therefore it directs other substituents to the ortho and para positions. The acetamido group is also a very large group and the ortho position is right besides the acetamido group. This creates steric hindrance from bromine from getting to the ortho position and therefore only para-bromoacetanilide or 4-bromoacetanilide is created mainly from a bromination of acetanilide.


What is a reason for low yield in the bromination of acetanilide?

A possible reason for low yield in the bromination of acetanilide could be the presence of impurities in the starting material. Impurities can compete for reaction sites or react in unwanted ways, leading to lower yields of the desired product. It is important to start with a pure sample of acetanilide to maximize the yield of the bromination reaction.


Why sodium sulphate is added in preparation of para bromo acetanilide?

Sodium sulfate is added in the preparation of para bromoacetanilide to facilitate the separation of the product from the reaction mixture. It helps in forming a complex with excess bromine and bromine water, allowing easy removal of impurities. Sodium sulfate is also used to dry the organic layer during the extraction process.


Is toluene will under go bromination?

Yes, toluene will undergo bromination. When treated with bromine in the presence of a Lewis acid catalysts such as FeBr3 or AlBr3, toluene will undergo electrophilic aromatic substitution to form bromotoluene as the major product.

Related Questions

Why acetanilide brominates in the ortho and para positions and the amount of o-bromoacetanilide?

Acetanilide undergoes bromination in the ortho and para positions due to the presence of the activating amino group that directs the electrophilic bromine to these positions. In the reaction mixture, the para-bromoacetanilide is the major product compared to the ortho isomer, typically in a ratio of about 4:1.


Why is only 4-bromoacetanilide created mainly from a bromination of acetanilide?

The Acetanilide is a benzene with a acetamido group attached to it. The acetamido group is electron donating and therefore it directs other substituents to the ortho and para positions. The acetamido group is also a very large group and the ortho position is right besides the acetamido group. This creates steric hindrance from bromine from getting to the ortho position and therefore only para-bromoacetanilide or 4-bromoacetanilide is created mainly from a bromination of acetanilide.


What is a reason for low yield in the bromination of acetanilide?

A possible reason for low yield in the bromination of acetanilide could be the presence of impurities in the starting material. Impurities can compete for reaction sites or react in unwanted ways, leading to lower yields of the desired product. It is important to start with a pure sample of acetanilide to maximize the yield of the bromination reaction.


Why sodium sulphate is added in preparation of para bromo acetanilide?

Sodium sulfate is added in the preparation of para bromoacetanilide to facilitate the separation of the product from the reaction mixture. It helps in forming a complex with excess bromine and bromine water, allowing easy removal of impurities. Sodium sulfate is also used to dry the organic layer during the extraction process.


Is toluene will under go bromination?

Yes, toluene will undergo bromination. When treated with bromine in the presence of a Lewis acid catalysts such as FeBr3 or AlBr3, toluene will undergo electrophilic aromatic substitution to form bromotoluene as the major product.


What product is obtain by bromiation of aniline using bromin?

The product obtained by bromination of aniline using bromine is 2,4,6-tribromoaniline. This reaction involves the substitution of hydrogen atoms on the benzene ring of aniline with bromine atoms.


Why is not recommended to obtain para -bromoacetanilide by bromination of aniline then acetylation?

Aniline is a benzene with an amine group attached to it. When you brominate aniline, since aniline is electron donating, it directs other substituents to the ortho and para positions. Therefore you will not only get para-bromoacetanilide. However if you just want para-bromoacetanilide, you should go through acetylation first because this changes the amine group on the aniline into an acetamido group which is very bulky and big, and also electron donating. Since it is so big, the bromine cant attach to the ortho positions because of the steric hindrance caused by the very bulky acetamido group and therefore you will get para-bromoacetanilide as your product.


Is pyridinium bromide perbromide a source of bromine or an oxidizing agent in prepration of Meso-Stilbene Dibromide?

Pyridinium bromide perbromide acts as an oxidizing agent in the preparation of meso-stilbene dibromide. It facilitates the bromination of the starting material (stilbene) by generating bromonium ions, which then attack the aromatic ring to form the dibromide product. It is not a direct source of bromine; rather, it helps in the bromination process by generating electrophilic bromine species.


What is the mechanism involved in the bromination of 3-methylcyclopentene?

In the bromination of 3-methylcyclopentene, a reaction called electrophilic addition takes place. This involves the addition of a bromine molecule (Br2) to the double bond in 3-methylcyclopentene, resulting in the formation of a bromonium ion intermediate. This intermediate is then attacked by a bromide ion, leading to the final product where a bromine atom is added to the carbon-carbon double bond.


What is the product of a reaction between bromine and aniline in non polar solvent?

The product of a reaction between bromine and aniline in a non-polar solvent is typically the bromination of aniline, where bromine substitutes a hydrogen atom on the benzene ring of aniline to form bromoaniline. This reaction is an electrophilic aromatic substitution reaction.


The major monobrominated product which results when methylcyclohexane is subjected to free radical bromination is?

1-bromo-3-methylcyclohexane is the major monobrominated product formed when methylcyclohexane undergoes free radical bromination. This occurs because the bromine radical prefers to attack the tertiary carbon due to its greater stability compared to primary or secondary carbons.


What is the product when testosterone undergoes bromination?

testeterone