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Experiment 5 The Preparation of Acetanilide from Aniline Goals To explore some reactions of amines. Objectives: 1. Preparation of acetanilide from aniline 2. Development of the following experimental techniques. use of decolorizing charcoal: folding and use of fluted filter paper, vacuum filtration, 3. Use of infrared data to detect the amine functional group 4. Differentiation of primary, secondary and tertiary amines using the nitrous acid test 5. Determine the melting point of acetanilide. . NH2 ( aqueous HCI CH of (6) sodium acetate aniline Na acetanilide ml (111) HO 0% (acetic anhydride) Introduction In this experiment aniline, a primary aromatic amine, is converted to an amide, acetanilide, essentially by reaction with acetic anhydride. In the past, acetanilide was used as an antipyretic (fever-reducing) and analgesic (pain-killing) drug but, due to its toxicity, it is no longer used for these purposes. However, acetanilide is still an important chemical which is used in the manufacture of medicinal compounds and of dyes. Today's synthesis entails the use of hydrochloric acid and sodium acetate, in addition to acetic anhydride. Both the HCl and the sodium acetate are integral parts of the reaction sequence leading to acetanilide. The worksheet and write-up will guide you in deciphering the roles of these reagents in this synthesis, Safety Notes You must wear eve protection at all times. In the event that any reagent used in this investigation comes in contact with your skin or eyes, wash the affected area immediately with lots of water. Notify your instructor. Aniline is toxic and can be absorbed through the skin. Use the fume hood. Concentrated hydrochloric acid can cause severe burns Acetic anhydride is lachrymatory: Procedure To 30 cm water in a 100 cm. Erlenmeyer flask add 1 cm' concentrated hydrochloric acid with mixing. In the fume hood add 1 cm'aniline (density 1.02 g cm-3) and swirl the mixture. If the solution is coloured, add a small amount of decolorizing charcoal, swirl the flask for about one minute, and filter of the carbon using a fluted filter paper (Appendix 7). In a separate container dissolve 1.5 g sodium acetate in 5 cm water. Warm the anilinium chloride solution to S0C on a water bath and add 2 cm' of acetic anhydride (density 1.08 g cm-). Swirl to effect dissolution 1 8 and add the aqueous sodium acetate quickly. Swirl the flask a couple of times and set it in an ice- bath for 20 min Filter, with suction, the crystals of the amide formed and wash with a small amount of ice-cold water. Dry the material between filter papers and submit your sample for assessment. Determine the melting point of the product. Inspect the infrared spectra of the starting material and product. In your write-up you will be asked to list the major bands and the groups which give rise to them (see Appendix 3) and to relate these data to the reaction which has occurred. Carry out the nitrous acid test (see Appendix D) on the l aliphatic amines and 19,2 and 3 aromatic amines provided. Record your results in tabular form, INFRARED SPECTRUM OF ANILINE TRANSMITTANCE (*) D 000 ens HO WAVENUMBER (CM) INFRARED SPECTRUM OF ACETANILIDE 100 TRANSMITTANCE (%) 1900 4F0D 3000 con WAVENUMBER (cro") (2) Aim Write a balanced equation for the reaction of aniline with acetic anhydride (3) - Brief summary of experimental procedure