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Title Alkanols &Alkanoic acids Data Collection, Data Processing and Presentation Part A: Alkanols A.

Reaction with sodium Table 1 Methodology Observation A small piece of sodium was added to 1 A vigorous reaction occurred and bubbles 3 cm of ethanol in a test tube of gas were produced. A lighted splinter was tested to the gas A pop sound was produced In aqueous state, alcohols such as ethanol (CH3CH2OH), dissociate1 according to the following equation: CH3CH2-OH (aq)

CH3CH2-O-(aq) + H+(aq)

When a small piece of sodium is added, sodium metal reacts with ethanol to liberate hydrogen gas2: 2CH3CH2OH (aq) + 2Na(s)

2CH3CH2ONa (aq) + H2 (g)

The hydrogen gas produces a pop sound when a lighted splinter is inserted into test tube containing the gas as the hydrogen meets the oxygen in the air. B.Reaction with organic acid Esterification Table 2 Methodology Observation A warmed mixture of 10 drops of ethanol + 10 drops of glacial ethanoic acid + 6 A fruity smell was produced drops of concentrated sulphuric acid was added to 50 cm3 of water in a beaker When a warmed mixture of alcohol such as ethanol (CH3CH2OH), and carboxylic acid such as glacial ethanoic acid (CH3COOH), with the presence of concentrated sulphuric acid as catalyst, is added to water, ester is formed3. CH3CH2OH (l) + CH3COOH (l)

CH3COOCH2CH3 (aq) + H2O (aq)

In the reaction, OH from ethanol breaks and reacts with H from ethanoic acid to form water. The remaining ions from both compounds react to form ethyl ethanoate which has fruity smell. C.Reaction with phosphorus halides

Lim You Sie. Text for PRE-U STPM Chemistry. Selangor: Pearson Malaysia Sdn. Bhd, 2003. (p. 486) 2 Ibid. (p. 488) 3 Ibid. (p. 488)

Table 3 Methodology Observation The fumes evolved from a mixture of phosphorus pentachloride and 10 drops of Some amount of white precipitate were ethanol were bubbled into silver nitrate formed solution When the fumes had subsided and the reaction was completed, the contents of A chloroform-like smell was produced the tube was poured into 50 cm3 of water in a beaker Alcohols react with phosphorus (V) chloride (PCl5), to produce a chloro-compound4. In this reaction, ethanol (CH3CH2OH) reacts with phosphorus (V) chloride (PCl5) and produces ethyl chloride, phosphoryl chloride and hydrogen chloride. CH3CH2OH (l) + PCl5 (s)

CH3CH2Cl (l) + POCl3 + HCl (g)

This reaction requires no heating because it is readily occurred at the room tempereature. When the white fumes (hydrogen chloride) are bubbled in silver nitrate, some amounts of white precipitate (silver chloride) are formed. HCl (g) + AgNO3 (aq)

AgCl (s) + HNO3 (aq)

The chloroform-like smell produced is because of ethyl chloride. D.Oxidation with acidified potassium manganate (Vll) Table 4 A mixture of 10 drops of dilute sulphuric acid, 5 drops of Methodology potassium manganate (Vil) solution and 5 drops of following alkanol was warmed and smelled gently Alkanol Ethanol Methanol Propan-2-ol The purple colour of the mixture was The purple colour of the mixture was reduced to Observation reduced to colourless and an unpleasant colourless and a smell was produced sweat smell was produced Primary alcohols and secondary alcohols react with acidified potassium manganate (Vll) to produce aldehydes and ketones respectively5. In this reaction, the purple colour of potassium manganate (Vll) is decolourised and this reaction requires heating. Ethanol and methanol are classified as primary alcohol and the oxidation with acidified potassium manganate (Vll) produces ethanal and methanal respectively which cause the unpleasant smell.

4 5

Ibid. (p. 489) Ibid. (p. 491)

Ethanol: CH3CH2OH (l) + [O] Methanol: CH3OH (l) + [O]

CH3CHO (l) + H2O (l) CH2O (l) + H2O (l)

Propan-2-ol is classified as secondary alcohol and the oxidation with acidified potassium manganate (Vll) produces propanone which cause the sweat smell. CH3CH(OH)CH3 (l) + [O] Part B: Alkanoic acids A.Physical properties of glacial ethanoic acid Table 5 Methodology Observation A test tube of glacial ethanoic acid was The glacial ethanoic acid was freeze and a put in a refrigerator for an hour colourless crystal was formed Glacial ethanoic acid is also called as pure ethanoic acid because it freezes at slightly below ordinary room temperature6. Its melting points is at 17 0C (62 F)7, so under 0 0 C, it will freeze easily and form a colourless crystal. B.Acid properties ethanoic acid Table 6 Solution (0.1 M) Ethanol Ethanoic acid Hydrochloric acid pH 7 2 0

CH3C(O)CH3 (l) + H2O (l)

From the results obtained, the pH of ethanol is 7. However, theoretically, ethanol is a weak acid where it partially dissociates in aqueous solution. CH3CH2-OH (aq)

CH3CH2-O-(aq) + H+ (aq)

For both ethanoic acid and hydrochloric acid, under same concentration, they have different pH values where the pH of ethanoic acid is 2 and the pH of hydrochloric acid is 0. This is because ethanoic acid is a weak acid while hydrochloric acid is a strong acid. Ethanoic acid will partially dissociate in water and produces less H3O+ ions compared to hydrochloric acid which is fully dissociated in water. Thus, ethanoic has higher value of pH compared to hydrochloric acid. Ethanoic acid: CH3COOH (l) + H2O (l) CH3COO- (aq) + H3O+ (aq) Hydrochloric acid: HCl (l) + H2O (l) Cl- (aq) + H3O+ (aq)
6 7

Acetic acid. Microsoft Encarta Encyclopedia Deluxe 2004. Version Redmond, USA. Ibid.

Table 7 Methodology Observation A mixture of 10 cm3of 2M sodium hydroxide and 5 cm3 of 2M ethanoic acid No smell produced was made in an evaporating basin A further amount of 2M ethanoic acid was added to the evaporating basin until The blue litmus paper changed to red the acid was excess. Blue litmus paper was submerged to identify the excess acid All water has left and white crystals The mixture was evaporated remained A few amount of dilute hydrochloric acid was added to a few of crystals in a test A distinguishing smell was produced tube and the mixture produced was warmed gently Carboxylic acids react with bases to form salts and water8. This process is called as neutralization. When sodium hydroxide and ethanoic acid is mixed together, salt which is sodium ethanoate, is produced and also water. NaOH (aq) + CH3COOH (l)

CH3COONa (aq) + H2O (aq)

An excess amount of ethanoic acid is added so that all sodium hydroxide will be neutralised and form sodium ethanoate. After evaporation, dilute hydrochloric acid is added to the crystals produced and this reaction forms ethanoic acid and sodium chloride. The distinguishing smell produced is because of the presence of ethanoic acid. HCl (aq) + CH3COONa (s) C.Oxidation Table 8 Methodology A mixture of 2 cm3 of glacial ethanoic acid and a few drops of potassium manganate (Vll) was warmed gently Observation The purple colour of potassium manganate (Vll) remained unchanged

CH3COOH (l) + NaCl (aq)

All carboxylic acids, except methanoic acid and ethanedioic acid, are not oxidised by oxidising agents such as potassium manganate (Vll)9. Although heating is applied during the experiment, the reaction still does not occur. This proves the stability of the structure of ethanoic acid. D.Dehydration Table 9 Methodology


Lim You Sie. Text for PRE-U STPM Chemistry. Selangor: Pearson Malaysia Sdn. Bhd, 2003. (p. 529) 9 Ibid. (p. 532)

2 cm3 of warmed concentrated sulphuric acid was added with a few drops of ethanoic acid

No gas came off except the colourless solution remained

Same like oxidation, all carboxylic acids, except methanoic acid and ethanedioic acid are not dehydrated by excess concentrated sulphuric acid10. This is because ethanoic acid will form a dimer where two hydrogen bonds are formed between two molecules of ethanoic acid. However, the dehydration will occur if stronger dehydration agents are used such as phosphorus pentoxide (P2O5).


Ibid. (p. 533)