Also, I find the description given in ( ) questionable, I think that the main. BACKGROUND. Principle: p-bromoacetanilide is prepared by bromination process. Mono substituted products of primary amine cannot prepared easily by direct. , Vol. 27, No. (1): Pg. Kinetics and Mechanism of the Bromination of Acetanilide. DILIP B. PATILĀ¹, GULABSINGH J. THAKURĀ² AND PARMANAND.

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That should block one of the two ortho positions sterically.

Synthesis of p-bromoacetanilide from acetanilide

Why does acetanilide gives exclusively para isomer. Post as a guest Name. Glacial acetic acid 70 ml. Synthesis of m-dinitrobenzene from nitrobenzene Organic Chemistry Here nitration is occurring on nitrobenzene.

The p-bromo acetanilide is obtained as colourless crystals, m.

It is an electrophilic aromatic substitution in presence of NO2, which is a Aniline undergoes nucleophilic substitution with bromine, qcetanilide in cold. Br2 does electrophilic aromatic substitution. Synthesis of salicylic acid from alkyl salicylate Organic Chemistry Alkaline hydrolysis of esters is called acetaniliee and is an irreversible process. Bromination of acetanilide gives para brominated acetanilide mainly, because amino group of acetanilide is protected by acetyl group.

We Labmonk, some scientific researchers unite to design a platform for getting sources of different lab protocols and discuss various research related issues. Thus, it is very likely that we can selectively stop the acefanilide after monobromination.


Where am I going wrong. X g of p-bromo acetanilide. We are introducing a sterically bulky group. Home Questions Tags Users Unanswered.

reaction mechanism – Bromination of acetanilide – Chemistry Stack Exchange

Acetanilide 10 g Glacial acetic acid 70 ml Bromine 4. Not giving equivalents, temperatures, solvents, reaction times etc. Used as analgesic and antipyretic.

Synthesis of 2, 4, 6-tribromoaniline from aniline Organic Chemistry Aniline undergoes nucleophilic substitution with bromine, even in cold. Do you have a link or a specific example in mind?

The conical flask is further rinsed with 50 ml cold water and transferred into the beaker with stirring. Turning the amino group into an amide serves two purposes: Chemistry Stack Exchange works best with JavaScript enabled.

Synthesis of p-bromoacetanilide from acetanilide – Labmonk

The question still arises why we only obtain the para -product. I am inserting the question and solution acstanilide for reference. The bromine atoms enter at the two ortho positions and If you would have used more equivalents, chances are good you would have gotten d as well.

It probably does give some of the ortho product.

Yet we can imagine the the proximity to the bulky amide group inhibits substitution at both ortho -protons sufficiently to allow isolation of the para -product. By using our site, you acknowledge that you have read and understand our Cookie PolicyPrivacy Policyand our Terms of Service.

Bromination is an electrophilic substitution reaction on an aromatic ring.


Mono substituted products of primary amine cannot prepared easily by direct action of a reagent. The yield of synthesized p-bromo acetanilide was found to be When an ethanolic solution containing acetone and its two equivalents of benzaldehyde is made alkaline with sodium hydroxide, rapid By clicking “Post Your Answer”, you acknowledge that you have read our updated terms of serviceprivacy policy and cookie policyand that your continued use of the website is subject to these policies.

Sign up using Facebook. Home Synthesis of p-bromoacetanilide from acetanilide.

Synthesis xcetanilide benzil from benzoin Organic Chemistry Here alcohol group of benzoin is oxidized to ketone group forming benzil in the presence of concentrated nitric acid Also, I find the description given in http: Complete hydrolysis can be rapidly obtained, if the ester is boiled under reflux with a dilute aqueous solution of Hence, there is not too much bromine there at a given moment and multiple bromination is prevented.

We expect the amide bond to be as acetanjlide as possible with respect to the benzene ring to maximise electronic interactions. Alkaline hydrolysis of esters is called saponification and is an irreversible process.

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