Because the amide group donates electrons into the pi system increasing the electron density - mainly at the ortho and para positions. The para position is however favoured as the ortho position is sterically hindered by the bulky amide group.
This report is a true record of all the observations and comprehensive explanations. What is the role of H2SO4 which added to the beaker after glacial acetic acid? Anonymous that is not an answer of this question. If glacial acetic acid is good nucleophile what will be the expected substitution that will occur? I like the reporty. In my case i optained a yellow product was my results wrong? Hey, i am looking for an online sexual partner ; Click on my boobs if you are interested.
Welcome to JAAN's science class!! Big hi to all of you! I'm an undergraduate following a Bsc in bioscience. Trust me I know the feeling of surfing around the net for ages and getting nothing in return!
Or getting something worthless for the time we spent surfing. So I started this blog adding the science stuff I have noted which I think might help someone in their home work. Ok then enjoy! Basically it can be carried out by a mixture of concentrated nitric acid and sulphuric acid.
Mixture is useful to obtain the active nitronium ion. Electrophilic aromatic substitution is a method used when a functional group is needed to be substituted on to an aromatic compound.
In the nitration, nitronium ion acts as the electrophile that involves the attack of the electron-rich Benzene ring. In this experiment nitration is carried out using acetanilide.
Acetanilide displays moderately reactivity in electrophilic aromatic substitution. Principally, acetanilide gives Ortho and Para mono nitroacetanilides. This is due to the resonance delocalizing the benzene ring by nitrogen lone pair. Therefore Ortho and Para positions are more resonance stabilized than the Meta. Acetanilide undergoes ready nitration giving mainly the colourless P-nitroacetanilide, mixed with much smaller proportion of the yellow colour O-nitroacetanilide.Principle: Here in first step electrophilic aromatic substitution nitration of nitronium ion is occurring towords para position of acetanilide more than ortho position due to steric reasons.
Nitronium ion is the electrophile generates from fuming nitric acid in presence of fuming sulphuric acid. In the second step p-nitroaniline is prepared from p-nitro acetanilide due to hydrolysis of acetate ion from acetamido functional group in presence of concentrated sulphuric acid.
Aim: To prepare p-nitro aniline from acetanilide. Step Use: It is an intermediate for dyes, pigents, pharmaceuticals Paracetamol, Phenacetin etc.
Glacial acetic acid. HNO 3. Glass rod.
Buchner funnel. Step 1: Preparation of p-Nitroacetanilide from Acetanilide. Add dry acetanilide 25 g to glacial acetic acid 25 ml in a beaker and then introduce concentrated sulphuric acid 50 ml slowly with constant stirring to obtain clear solution. Place the beaker in a freezing mixture of ice and salt to cool the solution below 5 o C.
Help with this theoretical yield problem?
Add a cold mixture of concentrated nitric acid 11 ml and concentrated sulphuric acid 7 ml drop wise with constant stirring to a reaction mixture while maintaining the temperature below 5 o C. After adding all the mixed acid, remove the beaker from the freezing mixture and keep it for 1 hr at room temperature.
Pour the reaction mixture into an ice cold water 30 ml to obtain the crude product of p- nitroacetanilide. Filter it on suction, wash with cold water till free from acid and recrystallize the pale yellow product from ethanol to get colourless crystalline solid, m.
Note: o -Nitroacetanilide remains in the filtrate due to its high solubility in water. Step 2: Preparation of p—Nitroaniline from p-Nitroacetanilide. Reflux the mixture for min. Wash it thoroughly with water. Recrystallize the product using a mixture of equal volume of rectified sprit and water or from hot water.The purpose of this experiment was to synthesize methyl nitro benzoate from methyl benzoate, as well as nitroacetanilide from concentrated nitric acid HNO 3and concentrated sulfuric acid H 2 SO 4 by using an electrophilic aromatic substitution reaction.
The HNO 3 and H 2 SO 4 were combined to form a nitrating solution, which was added to a mixture of methyl benzoate and H 2 SO 4and the same was done with acetanilide. Following recrystallization, melting point was used to identify and characterize the product of the reaction. The percent yield of this reaction for the recrystallized product was Concentrated sulfuric acid 0. Concentrated sulfuric acid 1 mL was added to methyl benzoate 0. After the acid mixture was added, the reaction mixture was removed from the ice to warm to room temperature, with stirring.
It was then transferred by Pasteur pipet into a beaker and stirred for five minutes. The methyl benzoate nitration formed white solid, and the acetanilide nitration for a light yellow solid. The crystals were the vacuum filtered with a Buchner funnel. The crude product was recrystallized by adding a distilled water and ethanol slowly while heating the product.
While cooling, the solution produced large white crystals for methyl benzoate nitration and light yellow crystals for the acetanilide nitration.
The mass, melting point percent yield were obtained. Through the use of electrophilic aromatic substitution, acetanilide is nitrated to nitroacetanilide, while methyl benzoate was nitrated to methyl nitrobezonate. The first step of the reaction involved in the donation of an electron pair, which generates the nitronium ion from nitric acid by protonation and loss of water, using sulphuric acid as the dehydrating agent.
The mechanism for methyl benzoate can be seen below. Figure 3: The mechanism of the nitration of methyl benzoate to methyl nitrobenzoate.
To prevent acetanilide from dinitrating, the nitrating solution of HNO 3 and H 2 SO 4 were added drop by drop to the acetanilide solution, so that the concentration of the nitrating agent is kept at minimum. The cooler temperatures were used to reduce the reaction rate and help to avoid over nitration. The electrophilic aromatic substitutions involved the replacement of a proton on an aromatic ring with an electrophile that becomes substituent.
The sulfuric acid protonates the methyl benzoate, which creates the resonance stabilized arenium ion intermediate. The ester group is the meta deactivator and the reaction takes place at the meta position because the ortho and para positions are destabilized by adjacent positives charges on the resonance structure.
Table 1: The weight, melting point, and percent yield of both Nitroactenilide and Methyl Nitrobenzoate. The actual yield of methyl nitrobenzoate is 0. The percent yield for the methyl benzoate electrophilic aromatic substitution reaction was The percent yield for the reaction with acetanilide was 6. Some impurities might be Ortho and Meta directing substances, as well as there could have been some experimental errors that occurred during the experiment such as not overheating solutions during the reactions.
These low yields may have resulted from poor recrystallization, product lost during transfer from one apparatus to another, or human error. The missing percent accounts for the impurities removed during recrystallization.
However, some product must have been lost in the acetanilide reaction recrystallization because of such a low percent yield. Therefore, the melting point is lower than it should be suggesting that an impurity is in the product. This impurity may have occurred due to poor recrystallization or it may have been picked up after recrystallization.
Therefore, the melting point of the product is a little lower than the literature value, suggesting that an impurity exists in the product from poor recrystallization of contact with an impurity during recrystallization.In the nitration of acetanilide, 0.
Nitration of Acetanilide and Methyl Benzoate
The moles of acetanilide used are 0. The molecular weight of p-nitroacetanilide is I wasn't given a equation, I was just given the mechanism of reaction but I found that the balanced chemical equation is. The difficulty with calculating a theoretical yield in this situation is that the acetanilide you used is not pure. You can only calculate a theoretical yield when you know the mass and moles of the starting material. In this reaction, there is a relationship between the acetanilide and the p-nitroacetanilide.
So, if you assume that the acetanilide was pure, then you began with 3. The mass of that product your theoretical yield is 3. Trending News. Hailey Bieber endorses Biden — while dad backs Trump.
Steel yourself emotionally for colder weather. Beware of appropriation posing as a costume. Falcons fire Dan Quinn as coach after start. Jon Bon Jovi: I'm the 'poster boy' for white privilege. Fauci: Trump ad takes my words out of context. Saints star benched for slugging teammate: Report. What was A. Green doing during this interception? Gal Gadot's casting as Cleopatra launches debate.After recrystallization the solution was cooled to room temperature before being filtered.
The solution and resulting crystals were not iced cold before filtration as suggested in the manual. The filtration process was carried out twice to properly remove all crystals from the solution.
Molar mass of nitroacetanilide: This ensures a selective reaction and helps isolate the desired products. Allow the resulting mixture to stand for approximately 20 minutes until it reaches room temperature. Do not leave the mixture for longer than 1 hour as secondary reactions may occur. References Unknown. Learn more about Scribd Membership Home.
Read free for days Sign In. Much more than documents. Discover everything Scribd has to offer, including books and audiobooks from major publishers. Start Free Trial Cancel anytime. Nitration of Acetanilide. Uploaded by Mishka Rawatlal.Synthesis of Acetanilide
Document Information click to expand document information Description: Observe how an Aromatic Electrophilic Substitution reaction takes place via the nitration of acetanilide i. Date uploaded Apr 28, Did you find this document useful? Is this content inappropriate? Report this Document. Description: Observe how an Aromatic Electrophilic Substitution reaction takes place via the nitration of acetanilide i.
Flag for Inappropriate Content. Download Now. Related titles. Carousel Previous Carousel Next. Preparation of p-nitroacetanilide- Dotsha J. Jump to Page. Search inside document.Recrystallization is a purification technique; it allows us to remove impurities in a sample. The idea is you place impure solid in a liquid such as water or ethanol.
After heating for little while, the solid will dissolve in the liquid also known as the solvent. When the solvent cools back down again, the solid will precipitate out of the solution and leave the impurities behind, still dissolved in the solvent. This should leave you with a purified solid. The solubilities of most solids in solution increase as the temperature of the solution increases.
In fact, we can add about another 30 grams of acetanilide to this solution and it would still dissolve- but once we added more than 80g, additional solid acetanilide would no longer dissolve, and we would have a suspension once more.
At this point the solution is said to be saturated. At this point, we have more acetanilide dissolved in the ethanol that it should be able to hold- 50g vs. We then collect the acetanilide via vacuum or gravity filtration. The liquid that remains after the filtration is known as the supernatant mother liquor or just mother liquor for short.
A good solvent for recrystallization is one that your compound not very soluble in at low temperatures, but very soluble in at higher temperatures. In this case, ethanol is just too soluble. Polar compounds are soluble in polar solvents such as water, methanol, and ethanol. Non polar compounds are soluble in non-polar solvents such as hexanes and diethyl ether.
The speed at which you allow a saturated solution to cool affects the size of the crystals that form!
Nitration of Acetanilide
This makes an important different- if you have smaller crystals, they are more likely to clog a filter! Everyone likes to get out of orgo lab as soon as possible, but a clogged filter could add a good minutes to your procedure.
So how do you remove it? By filtering the liquid- the black pepper will get stuck in the filter paper, and you can continue to recrystallize the liquid solution as normal.
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