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Reactions of Alcohols Experiment # 6 INTRODUCTION In chemistry, alcohol is a more general term, applied to any organic compound in which a hydroxyl

group (-OH) is bound to a carbon atom, which in turn is bound to other hydrogen and/or carbon atoms. The general formula for a simple alcohol containing no rings is CnH2n+1OH. Alcohols are in wide use in industry and science as reagents, solvents, and fuels. Ethanol and methanol can be made to burn more cleanly than gasoline or diesel. Because of its low toxicity and ability to dissolve non-polar substances, ethanol is often used as a solvent in medical drugs, perfumes, and vegetable essences such as vanilla. In organic synthesis, alcohols frequently serve as versatile intermediates. Many alcohols can be created by fermentation of fruits or grains with yeast, but only ethanol is commercially produced this way, chiefly for fuel and drink. Other alcohols are generally produced by synthetic routes from natural gas, oil, or coal feedstocks, for example via acid catalysed hydration of alkenes. I. Problem / Objectives To give students the opportunity to learn about alcohols To know more about testing alcohols

II. Apparatus Tripod Thermometer Filter paper Rubber tubing Alcohol lamp Wire gauze Cork Test tubes Dropper Beaker

Spatula

Water bath

Test tube holder

Stirring rod

III. Materials Ethyl alcohol[C2H5OH] acetic acid[CH3COOH] alcohol[C5H11OH] Methyl alcohol[CH4O] Iodine [I2] tert-butyl alcohol salicylic acid[C7H6O3 ] potassium iodide[KI] [C4H10O] sodium hydroxide[NaOH] Isopropyl alcohol[C3H8O] zinc chloride[ZnCl2] calcium carbide[CaC2 ] Sulfuric acid[H2SO4] Copper sulfate[CuSO4] amyl

Hydrogen chloride[HCl]

IV.

Procedures 1. Dehydration of Alcohol Place about 10 ml of ethyl alcohol in a test tube. Add about 1 gram of calcium carbide. Cork the tube loosely and warm at about 60C in a water bath for 10 minutes. (During this time go on with other parts of work). Cool the mixture, and filter through a dry filter paper and funnel into a recently dried test tube. Cork and save the filtrate for (2) and (3) Equation:

2. Test for water in Alcohol: (Note: If copper sulfate available is hydrous (blue crystal), heat it strongly until it is anhydrous (white powder) Place a powdered anhydrous copper sulfate in each of the two recently dried test tubes. Add 2 ml of 95% ethyl alcohol to one test tube and an equal amount of the prepared anhydrous alcohol to the other. In the presents of the instructor, add 1 drop of water to the anhydrous alcohol. Equation:

3. Esterification a. Mix in a test tube 1 ml each of ethyl alcohol and acetic acid and a little less than 1 ml of concentrated sulfuric acid, warm in a water bath for 20 minutes, then pour into 50 ml of cold water. Whats the odor? b. Repeat (a) using amyl alcohol instead of ethyl alcohol. c. Repeat (a) using methyl alcohol, salicylic acid, and concentrated sulfuric acid. Observations?

4. Iodoform test: To four drops of ethyl alcohol in 1 ml of water, add 3 drops of 8 N NaOH solution, then dropwise a solution of iodine in KI until a faint yellow color persists. Warm the mixture to about 60C, set aside for 5 10 minutes. Observations:

Equation:

5. Oxidation: Put ml of ethyl alcohol, isopropyl alcohol, and tert-butyl alcohol in 3 separate test tubes. To each, add 5 drops of potassium dichromate and 5 drops of dilute sulfuric acid. Warm in a water bath. Note the color and odor of the solutions. Compare the ease by which each of the alcohols oxidized. Observation:

Equations 6. Replacement of Hydroxyl with Halogen: The Lucas Test Place ml of each, ethanol, isopropyl alcohol, and tert-butyl alcohol in a separate test tube, and add 3 ml of HCl and ZnCl2 reagent to each, and warm in a water bath to 26-27C. Stopper the tubes, shake the mixture and allow to stand. A cloudiness in the solution is the first sign of a reaction. Observe the tubes at each of the following periods (1) Immediately upon mixing; (2) after standing for 5 minutes; (3) after standing for a hour. Observe the relative rates of reaction, and record your observations. Equations:

V. Observations / Questions

VI. Conclusion