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EXPERIMENT 5: ALCOHOLS AND PHENOLS

Eden Cabana, Niña Dominguez, Philip Gabriel Gimotea
Locker No. 21
Chemistry Department, Xavier University-Ateneo de Cagayan, Cagayan de Oro City
Date Performed: December 15,2014
Date Submitted: December 18, 2014

ABSTRACT
A functional group is an atom or group of atoms, bonded together in a certain
way, that as part of a molecule, will impart certain physical and chemical
characteristics to the molecule as a whole. It is the case that the rest of the
molecule can modify the characteristics of the functional group. It is also the case
that if the rest of the molecule is an alkyl group the modifications may be modest.
On the other hand, other functional groups in the molecule, especially if they are
close by, are more likely to profoundly modify the characteristics of the functional
group in question. Qualitative analyses of the different types of alcohols and
phenols were carried out. In the majority of experiment, four test samples were
used namely: ethanol, isopropyl alcohol, tertiary butyl alcohol, and phenol. With
these, the objectives of the experiment are to make an analysis of different types
of alcohols and phenols using different methods namely: the use of sodium
metal for the detection of acidic hydrogen in alcohols, the comparison of
oxidizing conditions of a compound using different solutions, the comparison of
oxidation rates of the different types of alcohols using one medium test, the
comparison of the relative acidity of phenol with other compounds, and phenol
reaction with bromine water; identify 1°, 2° and 3° alcohols; and distinguish
alcohols and phenols from other compounds. In each test, different samples were
used and each of their reaction was observed for any indications of a positive test.
These can be helpful in analyzing and identifying unknown compounds by
analyzing their properties. In some tests, several compounds experienced side
reactions due to contamination, unclean equipment, and poorly prepared reagents
that might have been stored for a long time already. Moreover, most of the tests
had limitations.

INTRODUCTION

MATERIALS AND METHODS
Apparatus
1) 25mL test tube
2) Lighter
3) Asbestos mat
1

C2H5OH 3) 10mL distilled water. To each test tube. List down the observations and write the equation that represents the reaction as Reaction 1a. Give a description and write the equation that represents the reaction as Reaction 1b. C₃H₈O 10) 1½ mL tertiary butyl alcohol. a stirring rod 2 . place 3 drops of ethyl alcohol. H₂O 4) Blue litmus paper 5) Red litmus paper 6) 6 drops of 0.4) Mat 5) Iron stand 6) Iron ring 7) Beaker 8) Bunsen burner 9) Wire gauze 10) Test tube holder 11) 1 Test tube rack 12) 2 Stirring rod Chemicals 1) Small clean piece of 2mm cube metallic sodium. 3mL of water and 2 drops of 0. Simultaneously place in test tube #2. 2-methyl2-propanol 11) 5 drops of K₂Cr₂O₇ 12) 1 drop of 6M sulfuric acid. Cool. Comparison of Oxidizing Conditions Set 3 test tubes in a rack.0002M KMnO₄ 7) 8M NaOH 8) 3mL concentrated HCl 9) 1½ mL isopropyl alcohol. Na 2) 9 drops and 2½ mL of anhydrous ethyl alcohol. a stirring rod which has just been dipped in 8M NaOH solution and in test tube #3. Interpret the results by answering these questions: a) What is the role of sodium metal in this procedure? b) What does the reaction of ethanol with sodium tell you about the acidity of alcohols? c) What property of alkoxide ions is exhibited in the experiment? B.0002 KMnO₄ solution (just enough to give the solution a pink color). add 1mL of distilled water and test the solution with litmus paper. Na₂CO₃ 15) 1mL 1% acetic acid. C₂H₄O₂ 16) 1mL 1-butanol Procedure A. Test for Acid Hydrogen in Alcohol Precaution: Sodium is highly reactive and should not be held with bare hands or be exposed to moisture Drop a small clean piece of metallic sodium (2mm cube) into a previously dried test tube containing 1mL of the anhydrous ethyl alcohol and immediately observe what happens after. Evaporate to dryness (in a water bath) after the reaction has ceased. C₆H₆O 14) 3mL sodium carbonate. H₂SO₄ 13) 1mL of 2% solution of phenol.

Compare the ease by which each of the alcohols is oxidized. D. For the relative ease of oxidation. Note the color and odor of the solutions. 2⁰ and 3⁰ alcohols Set 3 test tubes in a rack. F. and tertiary water soluble alcohols. Shake for a few minutes at room temperature and allow to stand. Compare & account for the difference in the rate of reaction of these alcohols. Comparison of Oxidation Rate of 1⁰. Provide an explanation for the differences in the rate of reaction. To each. secondary. Provide an explanation for the differences in the rate of reaction. Repeat the test using 1% solution of acetic acid and 1-butanol in 2 separate test tubes instead of phenol as the acid.which has just been dipped in concentrated HCl. Test for acidity in alcohol Step After dropping Na to ethanol Description Na dissolves in ethyl alcohol with the presence of bubbles. 2=moderate. Comparison of the Rate of Substitution or Lucas Test This test is used to distinguish among primary. Put ½ mL of ethyl alcohol in the first test tube. Acidity of Phenol Mix 1mL of a 2% solution of phenol with 1mL of a sodium carbonate solution. or neutral? For the relative ease of oxidation.017M K₂Cr₂O₇ and 1 drop of 6M sulfuric acid solution. transfer 1 mL each ethyl alcohol. 3=slow. 2=moderate. Take note of the alcohol which gives a surface layer of the alkyl chloride. E. 3=slow. write 1= fast. Note if carbon dioxide is evolved. Observe closely. C. Into 3 separate test tubes. add 5 drops of 0. 2=moderate. 3 Chem Reacti on 1a . Reaction of Phenol with Bromine Water Add bromine water dropwise to 5 drops of the phenol solution. isopropyl alcohol and tertiary butyl alcohol. Add an equal amount of concentrated HCl to each. Compare the acidity of phenol to acetic acid and 1-butanol based on the rate of reaction with sodium carbonate solution and account for the difference. write 1=fast. ½ mL isopropyl alcohol in the 2 nd test tube and ½ tertiary butyl alcohol in the third test tube. For the relative ease of substitution. The test tube also became hot. write 1=fast. RESULTS AND DISCUSSION Table 1. In which medium was the oxidzation (evidenced by decolorization) most rapid: acidic. Add 1mL of sodium carbonate solution to each. What is the solid so readily precipitated? Is phenol easier or more difficult to substitute with bromine than benzene? Give a chemical explanation in support of the choice made. 3=slow. Warm. basic.

There is some fizzing as hydro gas is given off. KMnO₄ Ease of Reacti Oxidation on Ethanol + First. the whole mixture became clear. which gave the pale pink color of the solution. it was observed that oxidation was fastest in the basic medium (NaOH) rather than the acidic one (H 2SO4). there were two layers the lower clear 1 2b KMnO₄ + part and the light green upper part. Chemical Equations: 1 2 C2H5OH + 2 Na = 2 C2H5ONa + H2 a 1 b 1b For the test of acidity in alcohol. Comparison of oxidizing conditions Alcohol + Description Relative Chem. Chemical Equations: 2 CH₃CH₂OH + KMnO₄ = CH₃COOH + H₂O + MnO₂ + K a 2 CH₃CH₂OH + KMnO₄ + NaOH = MnO₂ + CH₃COONa + 2 H₂O + K b 2 CH₃CH₂OH + KMnO₄ + HCl = CH₃COOH + MnO₄ + H₂O + 2 KCl c In comparing the oxidation of ethanol with potassium permanganate in solutions of different acidities. The acidity of alcohols in the reaction of ethanol with sodium doesn't require much phenol since it is a weak acid that leads the experiment into slow reaction. the upper part became darker. After a few (neutral minutes. the production of MnO 2 together 4 . Table 2. It is not directly able to react because of its acid. the upper part became yellow. Litmus paper was then used to test the solution. The after testing the solution red litmus paper turned blue while there were w/ litmus paper no changes in the blue litmus paper. After a NaOH few minutes. several bubbles are arising from the water surface because it indicates the presence of sodium which is highly relative.After evaporation of There is a presence of white residue solution After addition of water & The outer surface of the test tube was hot. Oxidation of ethanol and the reduction of potassium permanganate in H2SO4 produced acetic acid and Mn 2+. The role of the metal in this procedure is to distinguish the acid hydrogen from the used alcohol. there were two layers the lower clear 2 2c KMnO₄ + HCl part and the pink upper part. medium) Ethanol + First. there were two layers the lower clear 3 2a KMnO₄ part and the pink upper part. Ethanol + First. On the other hand. It is when it identifies the acidity of the compound in every procedure. After a few minutes. The mixture left in the tube will contain sodium phenoxide.

the alcohol is first oxidized to an aldehyde which is then oxidized further to the acid. Table 4. yellow above a white liquid (C2H5OH) Secondary Alcohol Homogenous aqueous transparent-white 2 3b used colored mixture ( C₃H₈O ) Tertiary Alcohol Homogenous aqueous clear yellow 3 3c used mixture ( 2-methyl2propanol ) Chemical Equations: 3 K₂Cr₂O₇ + H₂SO₄ + C₂H₆O = Cr₂ (SO₄) ₃ + CO₂ + K₂SO₄ + H₂O + C₂H₄O₂ a 3 5 C3H8O + K2Cr2O7 + 4 H2SO4 = Cr2(SO4)3 + K2SO2 + 5 CH3CH2CHO + 9 H2O b 3 26 C4H10O + K2Cr2O7 + 2 H2SO4 = 26 C4H9O + 2 KCrS + 15 H2O c Oxidation mechanism of alcohols is different for different types of alcohols. Secondary alcohols are oxidized to ketones . There is no reaction whatsoever. 2ᵒ. If you look at what is happening with primary and secondary alcohols. 3ᵒ Alcohols Alcohol + Description Relative Chem. Comparison of Rate of Substitution of Alcohol (Lucas Test) Description Relative Alcohol + Conc. Acidic K₂Cr₂O₇ Ease of Reacti Oxidation on Primary alcohol Aqueous mixture with a formation of 2 1 3a used layers. Ease of HCl Substitut ion Primary Alcohol (C2H5OH) 5 Chem. if you heat the secondary alcohol propan-2-ol with potassium dichromate(VI) solution acidified with dilute sulfuric acid.and that's it. In the case of the formation of carboxylic acids. Reacti on 4a . Oxidation did not happen in water since it is a neutral solution and did not cause redox reactions. Tertiary alcohols aren't oxidised by acidified sodium or potassium dichromate(VI) solution. Tertiary alcohols don't have a hydrogen atom attached to that carbon. For example. Comparison of Oxidation Rate of 1ᵒ. Primary alcohols can be oxidized to either aldehydes or carboxylic acids depending on the reaction conditions.with acetic acid from the reaction of ethanol in a NaOH solution resulted in the green color of the solution. Table 3. you get propanone formed. and a hydrogen from the carbon atom attached to the -OH. you will see that the oxidizing agent is removing the hydrogen from the -OH group.

Secondary Alcohol ( C₃H₈O ) Tertiary Alcohol ( 2-methyl2propanol ) Chemical Equations: 4 C2H5OH + HCl = C2H5Cl + H2O a 4 C3H7OH + HCl = C3H7Cl + H2O b 4 C4H10O + HCl = C4H9Cl + H2O c 4b 4c Lucas test is used to classify and distinguish alcohols as primary. The OH group of the alcohol attracts the H in hydrochloric acid to form oxonium ion and leave the group (form water). secondary. http://1chemistry. In isopropyl alcohol. it does not react appreciably with Lucas reagent at room temperature especially with ethyl. it react immediately by which it is called to be the turbidity. It is based on the difference in reactivity of the three classes of alcohols with hydrogen halides. or tertiary alcohols.com/2011/05/properties-of-alcohol. what causes to take more than a minute or a slow reaction is its solubility with the reagent while in tertiary butyl alcohol. Relative Acidity of Phenol Chem. The second layer (cloudy layer) formed is alkyl chloride which is insoluble in the aqueous solution because all the alkyl halides molecules are insoluble in the water. the formation of two layers (aqueous layer and cloudy layer) is known as a positive test. Name of Reacti Compound on Tested Phenol 5a ( C6H6O ) Alcohol used 5b ( C2H4O2 ) Carboxylic Acid 5c used Chemical Equations: 6 .html Table 5. In Lucas test.blogspot.(nucleophile) to produce the alkyl halide product. For all the alcohols. The carbocation intermediate is formed and tends to react with Cl. owing to the low solubility of the organic chloride in the aqueous mixture or liquid mixture. It was observed to be the fastest to give the rate because it involves the transformation of carbohydrates in which the reaction of the alcohol is determined by the ease of formation of the carbonation. Family/ Description Chem. The alcohols with the properties of generating a stable carbocation intermediates will undergo the particular reaction. The alkyl chloride produced from the reaction is not water-soluble and causes cloudiness (emulsion) to form in the aqueous solution. The reaction that takes place on the Lucas test is a SN1 nucleophilic substitution.

The precipitate is 2. phenol is more acidic than 1-butanol and less acidic than acetic acid. A hydrogen ion can break away from the -OH group and transfer to a base. and it does not react with sodium carbonate or hydrogencarbonate solutions.uk/candrands/arenes.5 2 C6H6O + Na2CO3 = 2 NaOH + 2 C6H5 + CO3 a 5 Na2CO3 + 2 C2H4O2 = CO2 + H2O + 2 NaC2H3O2 b 5 c Compounds like alcohols and phenol which contain an -OH group attached to a hydrocarbon are very weak acids. Unlike the majority of acids. like nitro. will increase the acidity of phenols and carboxylic acids because they stabilize the phenoxide and carboxylate anions that are produced as the acid gives up its proton Table 6.4.even if it is still a very weak acid. the bromine water is decolorized and a white precipitate is formed which smells of antiseptic. However. Reacti on 6a EAS halogenations without Lewis acid as catalyst Chemical Equations: 6 Br₂H₂O + C₆H₆O = C₆H₆ + H₂O + Br₂O a When adding bromine water to a solution of phenol in water. Electron withdrawing groups. because of the hydroxyl group attached to it. http://www.6-tribromophenol. phenol is sufficiently acidic for it to have recognizably acidic properties . the benzene ring in phenol is about 100 times more reactive in benzene itself.me. phenol does not give carbon dioxide when you mix it with sodium bicarbonate. Unlike other arenes. You can recognize phenol because it is fairly insoluble in water. Therefore. though it still undergoes a substitution reaction. phenol does decolorize bromine water. it reacts with sodium hydroxide solution to give a colorless solution. Carboxylic acids are usually stronger acids than phenols and phenols are stronger acids than alcohols. Reactivity of Phenol with Bromine Water Reactions Description Chem.htm CONCLUSION REFERENCES: 7 . Thus.chemistryrules. Phenol is not acidic enough to react with sodium bicarbonate or the carbonate and hydrogencarbonate ions are not strong enough bases to take a hydrogen ion from the phenol.