Experiment 9: Synthesis of Organic Compounds A. Synthesis of 1-phenylazo -2-napthol Data and Results 1.

Theoretical Yield: Actual Yield: Percent Yield: 2. Physical Properties of the Product Appearance: mud block Color: red orange Texture: fine Odor: rugby Chemical Tests: Test Performed 0.1M NaOH 1.0M HCl NH4OH CH3COOH

3.

Observations

Questions: 1. What reactions are involved in the synthesis of 1-phenylazo -2-napthol? A. DIAZOTIZATION  Preparation of solution of diazonium salt and benzene diazonium chloride from aniline. HCl or H2SO4 ANILINE + NaNO2 → PHENYLDIAZONIUM CHLORIDE +2 H2O

B. DIAZONIUM-COUPLING REACTION  Diazonium salt attacks the carbon in the ortho- and para- positions with respect to the activating group attached to the benzene.

1 Chem 31.1 Experiment 9

The iodide ion in starch reacts with nitrous acid to form a blue complex. 5.2. The blue coloration on the starch iodine paste will indicate excess nitrous acid since all iodide has been oxidized. Write the reaction pathway and mechanism for the synthesis of 1-phenylazo -2-napthol. Applications: B. Why is the rate of the phenyldiazonium ion with β-naphthol dependent upon the pH of the reaction medium? If the acidity of the reaction medium is high. Nitrous acid oxidizes iodide ion to form iodine. the amines will be converted to ions thus they cannot undergo aromatic substitution reaction slowing the coupling reaction. Synthesis of Soap Data and Results 1.1 Experiment 9 . 4. Theoretical Yield: Actual Yield: Percent Yield: 2. 3. Explain the principle behind the use of starch iodine paste in detecting excess nitrous acid. Why should the temperature of the reaction mixture be kept in 5oC? The diazonium salt will easily decompose back to aniline at temperature higher than 5oC. Physical Properties of the Product 2 Chem 31.

3 Chem 31. The products formed are alcohol and salt. Chemical Tests: soft liquid cream soft fragrant Test Performed pH Calcium chloride Magnesium chloride Ferric chloride Oil with soap Oil with water Observations white precipitate white precipitate white precipitate with layer no layers Questions: 1. The orthoester rearranges to form a carboxylic ester and an alkoxide Proton transfer takes place since the OR group is more basic than RCOOH. ALKALINE HYDROLYSIS  Reaction with water or dilute alkali of triglyceride (fat or oil).Appearance: Color: Texture: Odor: 3. What reactions are involved in the synthesis of soap? A. Triglyceride is reacted with lye or other strong bases produce glycerol and fatty acid salts (soap) → 2.1 Experiment 9 . B. Write the reaction pathway and mechanism for the synthesis of soap The hydroxide ion from NaOH attacks the carbonyl group of the ester to give an orthoester.

Theoretical Yield: Actual Yield: Percent Yield: 2. Physical Properties of the Product Appearance: crystalline Color: fine Texture: white Odor: vinegar-like Chemical Tests: Test Performed 3. Why was the dilute soap solution poured in a solution of sodium chloride in water? The addition of NaCl solution to the soap solution will precipitate the soap. 4. Applications: Would soap be a reasonable choice for the emulsifying agent if the water were slightly acidic? Why? No. and ferric chloride solutions. Observations 4 Chem 31. The long hydrocarbon chain of the soap is non-polar and hydrophobic while the "salt" end of the soap molecule is ionic and hydrophilic. How doe soap function as an emulsifying agent for oil in water? Draw a picture of an oil droplet and several soap molecules to illustrate your answer. 5. C. because the soap will not be able to form a bridge between oil and water because of the H+ attached to the polar end of the soap instead of water so an emulsion will not occur. magnesium chloride.3. Explain the result obtained when the dilute soap solution is treated with calcium chloride. Synthesis of Aspirin Data and Results 1. Detergent can be used in place of the soap since it can tolerate slightly acidic water.1 Experiment 9 .

1 Experiment 9 . it is expected to give a positive result.Ferric Chloride Questions: 1. Explain why in the recrystallization of Aspirin the water should not be heated above 80C. Write the reaction pathway and mechanism for the synthesis of Aspirin. When the synthesized aspirin gives purple solution upon the addition of ferric chloride then not all the salicylic acid were consumed. Which is the stronger acid? Which would be more easily hydrolyzed in an alkaline medium? Why? Aspirin is more acidic than salol because of the stability of its conjugate base and its –COOH functional group. What reactions are involved in the synthesis of Aspirin? no reaction ESTERIFICATION  acid-catalyzed reaction of a carboxyl (-COOH) group and an -OH group of an alcohol or phenol to form a carboxylate ester 2. Ferric chloride reacts with phenol to give a purple solution and since salicylic acid has a phenol group. Aspirin may decompose back into salicylic acid and acetic anhydride when the temperature is too high. Explain the results obtained when Aspirin and salicylic acid were treated with Ferric chloride solution. 5 Chem 31. Aspirin will be hydrolyzed easily because it is acidic. 4. 3. Applications: Aspirin and salol are both acidic substances.

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