You will be asked to calculate percent yield on every lab you do for the rest of. To prepare and submit acetanilide from aniline labmonk. In the presence of strong acids, oximes can undergo molecular rearrangement to. Aniline is refluxed with glacial acetic acid in the presence of fused sodium acetate when acetanilide is obtained. Nitro anilines can be prepared by this type of reactions because nitration of aniline is not possible, amino group gets oxidised with nitrating mixture. Presents the preparation of sulfanilamide from aniline, a synthesis that is shorter than the tradition method. The preparation of acetanilide from aniline and ac. Difference between aniline and acetanilide compare the. In this experiment, acetanilide was produced by acetylation of aniline with acetic anhydride. Separate the aniline from the aqueous mixture extract with ether remove the ether simple distillation or reduced pressure distillation vacuum distil the aniline. Experiment 8 the preparation of acetanlide free download as word doc. A mixture of aniline, glacial acetic acid, acetic anhydride and zinc dust is refluxed under anhydrous condition and then poured the mixture into ice cold water to get acetic anhydride precipitate.
Nacetylarylamine has analgesic and feverreducing properties. Relative reactivies of anisole aniline and acetanilide. The difference in their functional group leads to other subtle variations in physical and chemical properties between these two compounds. If inhaled if breathed in, move person into fresh air. Sulfanilamide is easily synthesized from aniline in four steps. Acetanilide is prepared from aniline by acetylating it with acetic anhydride in the presence of glacial acetic. Prolonged heating and use of excess of acetic anhydride should be avoided. Preparation of phenylamineaniline chemistry stack exchange.
Acetanilide can be produced by reacting acetic anhydride with aniline. For the love of physics walter lewin may 16, 2011 duration. Preparation of acetanilide i take a 100 ml clean and dry r. Preparation acetanilide aniline from aniline in the laboratory. If the reaction mixture has been kept excessively cold during the addition. It is not as basic as ammonia, since protonation destroys the interaction between the ring and the lone pair on the nitrogen atom, but even still, it is sufficiently basic pkb 9. Preparation of acetanilide chemistry practicals class 12. Predicting the product of bromination of acetanilide. To prepare acetanilide the replacement of one hydrogen atom of the nh2 group of aniline by ch3co group in the presence of glacial acetic. Acetanilide, synthetic organic compound introduced in therapy in 1886 as a feverreducing drug. Show this safety data sheet to the doctor in attendance. To prepare a sample of acetanilide from aniline chemistry lab manualncert solutions class 12 chemistry sample papers theory acetanilide is prepared by acetylating aniline with acetic anhydride in the presence of glacial acetic acid. First aid measures general advice consult a physician. In an aqueous solution containing sodium bicarbonate, aniline reacts quickly with bromine to give 2,4,6tribromoaniline.
Acetylation of aniline experiment chemistry libretexts. Nitration of aniline requires very strong conditions, however, and the yields mostly mnitroaniline are poor. Stirring with a glass rod may be necessary to help dissolve the acetanilide r. Aniline is an aromatic amine with nh 2 group, and acetanilide is an aromatic amide with conh group. This is the method used in the preparation of acetanilide from aniline. You have seen the mechanisms for all of the steps, although some of the reagents may be unfamiliar.
After all the hno 3, h 2 so 4 solution has been added, the reaction mixture is allowed to warm slowly to room temperature. Acetanilide is synthesized from aniline by acetylating it with acetic anhydride in presence of glacial acetic acid. Apparatus round bottom flask 100 ml, water condenser, wiregauze, tripod stand, burner, ironstand. To prevent dinitration of the acetanilide, the nitrating mixture is added in small portions to the acetanilide solution and not vice versa so that the concentration of hno 3, is kept at a minimum. Key difference aniline vs acetanilide aniline and acetanilide are two benzene derivatives with two different functional groups.
The altmetric attention score is a quantitative measure of the attention that a research article has received online. Aniline is used to make a wide variety of products such as polyurethane foam, agricultural chemicals, synthetic dyes, antioxidants, stabilizers for the rubber industry, herbicides. Learning activity 1 preparation of acetanilide abstract recrystallization is a common method of purifying organic substances through the difference in solubility at different temperature. A solution of sodium acetate will be added as a base to deprotonate the water soluble intermediate and to. Acetic anhydride, an anhydride of acetic acid, acts here as a source of acyl group. To this mixture taken in the flask, add 5 ml of aniline and fit a water condenser. Acetanilide is prepared from aniline using an acetylation reaction. If you look at what you did, it is the same steps in a different order. A simple laboratory report on the preparation of acetanilide in the laboratory. Experiment 8 the preparation of acetanlide acetic acid.
Now, in the hood,prepare the bromine solution by adding 1. The synthesis of acetanilide comes about by the acylation of aniline with carboxylic acids. Aniline is a clear to slightly yellow liquid with a characteristic odor. Dissolve 2 g of aniline in 60 ml water and 2 ml conc. Its effectiveness in relieving pain was discovered soon thereafter, and it was used as an alternative to aspirin for many years in treating such common complaints as headache, menstrual cramps, and rheumatism. Acetanilide is an odourless solid chemical of leaf or flakelike appearance. To purify acetanilide by crystallization method using water. Bromination of acetanilide chemistry stack exchange.
It is usually prepared by acetylation of aniline with acetic anhydride and glacial acetic acid. The preparation of acetanilide from aniline and acetic anhydride is a specific reaction that can be applied to the preparation of any amide from the corresponding amine and anhydride as shown by the following generic equation. Aniline reacts with acetic anhydride to form acetanilide and the reaction is called acetylation. Aniline or phenylamine is a primary amine and basic in nature. Preparation of acetanilide from aniline amrita online lab. The crude acetanilide was dissolved in a solvent in a heating water bath. In order to protect the amino group from oxidation acetanilide is first nitrated to give pnitroacetanilide and then on hydrolysis to give pnitroaniline which is difficult to obtain by direct. In this reaction, aniline acts as the nucleophile and acyl ch 3 co. Preparation of acetanilide chemistry practicals class 12 byjus. Based on the above equation, complete the following equation for the preparation of phenacetin, a compound once used as an analgesic. They are then able to compare the melting points of the impure and recrystallized acetanilide. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. Preparation of paminoazobenzene from aniline akzo n. Preparationrecrystallization of acetanilide mendelset.
Learn more about these metrics article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. Nacetylarylamine is an odourless solid chemical of leaf or flakelike appearance. Aniline is toxic and can be absorbed through the skin. Preparation of dibenzal acetone materials required. Preparation of acetanilide college of science chemistry department 1 preparation and purification of acetanilide purpose. Take 5 ml of acetic anhydride in a clean dry 100 ml conical flask and add 5 ml of glacial acetic acid and shake the contents thoroughly.
Add 5 ml of distilled water to the test tube and then add 20 drops of acetic anhydride again using a medicine dropper fig. Aniline is slightly soluble in water and mixes readily with most organic solvents. Freshly distilled aniline should be used to get good results. The first step involves the addition of a protecting group to the amino substituent of aniline. The preparation used to be a traditional experiment in introductory organic chemistry lab classes, but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical. Acetanilide is prepared from aniline when it reacts with acetic anhydrideglacial acetic acid in the presence of zinc dust. Preparation of acetanilide from aniline pharmadhunia. Concentrated hydrochloric acid can cause severe burns.
Separate the aniline from the aqueous mixture extract with ether. To synthesis acetanilide by reaction of aniline and acetic anhydride amine to amide. These metrics are regularly updated to reflect usage leading up to the last. Reaction mixture should first cooled and then poured in icecold water otherwise hydrolysis of acetanilide may take place. Pdf we described herein a solventfree synthesis of acetanilide developed in the context of green chemistry. These metrics are regularly updated to reflect usage leading up to the last few days. Why does aniline dissolve in hcl, where acetanilide does not. Bromination of acetanilide journal of chemical education. The preparation used to be a traditional experiment in introductory organic. Thanks for a2a aniline when treated with acetoacetate will produce nacetyl aniline. Journal of chemical education, v56 n7 p488 jul 1979.
Presents an improved technique for synthesizing acetanilide from nitrobenzene by reducing nitrobenzene with iron powder and hydrochloric acid. It is also known as acetanilide, nphenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name antifebrin. This experiment has been used successfully with 2,000 students during. Hcl 37% hcl by weight in water is added in order to dissolve the aniline in water. Chemistry stack exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext.
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