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Glacial acetic acid is a trivial name for water-free (anhydrous) acetic acid

As a general term, a substance is said to be anhydrous if it contains no water.

Glacial acetic acid is an excellent polar protic solvent, as noted above. It is frequently used as a solvent for recrystallization to purify organic compounds.

Acetic acid is often used as a solvent for reactions involving carbocations, such as Friedel-Crafts alkylation; here acetic acid acts both as a solvent and as a nucleophile to trap the rearranged carbocation.

run in a glacial acetic acid in order to dissolve the starting materials

Glacial acetic acid (pure anhydrous acetic acid) is used as the reaction solvent, but it also plays an important role as an acid catalyst. Note that the halogenation reaction requires the reactant ketone be tautomerized to the enol form, which occurs under acid catalysis (base catalysis on the other hand would yield the corresponding enolate anion). So as the Br2 consumes the enol form by reacting with it, more enol will need to be generated and the acetic acid increases the rate at which this happens, thereby accelerating the overall reaction. The tautomerization mechanism involves simply protonation of the carbonyl oxygen of the ketone followed by deprotonation of its alpha carbon (carbon adjacent to the carbonyl carbon), with replacement of the CO double bond with a single bond and the formation of a double bond between the carbonyl carbon and the alpha carbon.

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10y ago
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12y ago

mechanism of p-bromoanilide from acetanilide

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11y ago

it just polarise the Br-Br bond and generate electrophile Br+

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Q: What is the mechanism of para bromoacetanilide reaction?
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Why acetanilide brominates in the ortho and para positions and the amount of o-bromoacetanilide?

The polarization of bromine in bromoacetanilide reaction


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.


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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.


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What is 4 Bromoacetanilide used for?

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What is use of p-bromoacetanilide?

Antipyretic and Analgesic