UNIVERSITI PENDIDIKAN SULTAN IDRIS

SKO 3013 BASIC ORGANIC CHEMISTRY LABORATORY REPORT 4 EXPERIMENTS FOR ALCOHOL

NAME SITI NOR AMIRA BT MOHMAD NOOR NORHIDAYAH BINTI MOHD AMIN

MATRIC NUMBER D20091035073

D20091035082

PENDIDIKAN SAINS SEMESTER 1 (2011/2012) LECTURER: DR SARIPAH SALBIAH BT SYED ABDUL AZZIZ.

Experiment 4: Alcohol Objective: student will be able learned:1. Chemical test to identify the existence of alcohol 2. Differentiation of different class of compound. Introduction:The first process of successfully identifying an unknown organic compound is to determine what functional group are present or absent in the unknown. In this experiment we will perform a series of chemical test on known compounds that have different functional groups. We will carefully note changes during the reaction. And record the result for both positive and negative test. Procedure: A. Solubility Test

Place 5 drops a liquid compound In small test tube

Add 10 drops distilled water

Fix the rubber stopper

Shake it

Record the observation, whether it mix partial, complete soluble or insoluble

B. Lucas Test. Prepare 3 dry and clean test tube for liquid compound

Label ( A,B,C ) for 1-Hexanol, 4-methyl-2-pentanol, and 2-methyl-2-pentanol.

Add 3 drops for each liquid compound in each test tube.

Add 10 drops lucas reagent in each test tube

Swirl the test tube

Observed the formation of cloudiness for at least 10 min.

Record the time it taken to turn cloudy

C. Tollen test Prepare 3 dry and clean test tube and risind it with 10% NaOH label (A,B,C) (to avoid from others reaction occur)

Add 1 mL of 5% AgNO3 and 10 drops of 10% NaOH for each test tube

Add 5 drops NH3 (conc) for each test tube

Shake until precipeted dissolves

Add 10 drops each liquid compound into test tube that have been labelled

Put into water bath until the coated mirror is formed.

Record the result

Disspose the chemical into drain with lots of running water

D. Chromic Acid Test. Prepared 3 dry and clean test tube

Place 2 drops of liquid compounds in each test tube and label (A,B, C) (dissolved the solid compound in about 5 drops of acetone)

Add 1 drop of Chromic acid solution.

Observed carefully

Positive reaction occurance of a precipitate . Observed it colour and the time took for form precipitated.

Result: A. Solubility test Compound 1-hexanol 4-methyl-2-pentanol 2-methyl-2-pentanol Solubility Slightly soluble Partially soluble Soluble

B. Lucas test Compound 1-hexanol 4-methyl-2-pentanol 2-methyl-2-pentanol Time taken for formation of cloudiness 30 minutes 3 minutes 20 seconds

C. Tollen test Compound 1-hexanol 4-methyl-2-pentanol 2-methyl-2-pentanol Formation of silver mirror coating Yes No No

D. Chromic acid test Compound 1-hexanol 4-methyl-2-pentanol 2-methyl-2-pentanol Colour changes Orange Orange blue green blue green Time taken precipitate form 30 seconds 90 seconds -

No changes

Question: write the complete chemical equation for liquid compound that the positif test in 2,4-dinitrophenylhydrazine test, iodoform test and chromic acid test. LUCAS TEST ________________________________________________________________________ CH3CH2CH2CH2CH2CH2OH + HCl (1-hexanol) ________________________________________________________________________ CH3 OH CH3 Cl

ZnCl2

CH3CH2CH2CH2CH2CH2Cl + H2O

CH3CHCH2CHCH3 + HCl (4-methyl-2-pentanol)

CH3CH2CHCH2CHCH3 + H2O

________________________________________________________________________

OH

Cl

CH3CH2CH2CCH3 + HCl CH3 (2-methyl-2-pentanol)

CH3CH2CH2CCH3 + H20 CH3

___________________________________________________________________________ TOLLENS TEST O CH3CH2CH2CH2CH2CH2OH (1-hexanol) O CH3CH2CH2CH2CH2C NH4 + 3NH3 + H2O + 2Ag ___________________________________________________________________________ CH3CH2CH2CH2CH2C (aldehyde) H + 2[Ag(NH3)2]+ + 2OH

CH3

OH

CH3

CH3CHCH2CHCH3 (4-methyl-2-pentanol)

CH3CHCH2CCH3 (ketone)

___________________________________________________________________________ OH CH3CH2CH2CCH3 CH3 (2-methyl-2-pentanol) __________________________________________________________________________ no reaction

CHROMIC ACID TEST O CH3CH2CH2CH2CH2CH2OH + H2CrO4 CH3CH2CH2CH2CH2C H + Cr2(SO4)3 + H2O (1-hexanol) (red-orange) (aldehyde) (blue-green)

___________________________________________________________________________ CH3 OH CH3 O

CH3CHCH2CHCH3 + H2CrO4 CH3CHCH2CCH3 (4-methyl-2-pentanol) (red-orange) (ketone)

Cr2(SO4)3 + H2O (blue-green)

___________________________________________________________________________ OH No Reaction

CH3CH2CH2CCH3

H2CrO4

CH3 (2-methyl-2-pentanol) ___________________________________________________________________________

Discussion: Alcohols contain the OH (hydroxyl) functional group attached to a saturated carbon.

Alcohols are classified into three categories which are primary (1), secondary (2) and tertiary (3) alcohol. This classification is based on the number of carbon-containing groups (R for an alkyl or an aromatic group) attached to the carbon bearing the hydroxyl group. In a primary (1) alcohol, the carbon which carries the -OH group is only attached to one alkyl group. There is an exception to this. Methanol, CH3OH, is counted as a primary alcohol even though there are no alkyl groups attached to the carbon with the -OH group on it. In a secondary (2) alcohol, the carbon with the -OH group attached is joined directly to two alkyl

groups. In a tertiary (3) alcohol, the carbon atom holding the -OH group is attached directly to three alkyl groups. SOLUBILITY TEST Alcohols and water are similar in certain properties because of the presence of the OH group in the molecules. They before have the ability to form inter molecular hydrogen bonding with each other and with water molecules. Alcohols with one to three carbon atoms are completely soluble in water. The OH group gives an alcohol a hydrophilic character. Alcohols with four to ten carbons atom are oily liquid and those with more than eleven carbon atom are solids, that are most insoluble in water. Solubility decrease when the relative molecular mass increases because of the longer hydrophilic area (R group). For alcohols with the same relative molecular mass, solubility increases with increasing number of OH group because the ability to form more hydrogen bonds with water molecules. From this experiment tertiary alcohol is more soluble in water compared with secondary and primary alcohol. It is because the branched alcohol (tertiary alcohol) provides higher solubility compared to unbranched alcohol (primary alcohol). It is due to the branch alkyl which have compact of hydrophobic group in tertiary alcohol. In primary or secondary alcohol, the hydrophobic area is less compact than in tertiary alcohol. The hydrophobic group are forcing their way between water molecules and so breaking hydrogen bonds between those water molecules. The -OH end of the alcohol molecules can form new hydrogen bonds with water molecules, but the hydrophobic group doesn't form hydrogen bonds. That means that quite a lot of the original hydrogen bonds being broken aren't replaced by new ones. Original hydrogen bonds are van der Waals dispersion forces between the water and the hydrophobic group. These attractions are much weaker. The more compact of the hydrophobic group of the alcohol, the more soluble in water. LUCAS TEST The Lucas reagent contains zinc chloride and hydrochloric acid. When the Lucas reagent is allowed to react with an alcohol, an alkyl chloride is formed. This alkyl chloride will not be soluble in water, thus cloudiness or a second layer of droplets will form if the test is positive. The appearance of a milky suspension in the reaction mixture indicates that a reaction has taken place. Alcohols react at different rates, depending upon their structure. Tertiary alcohols form a cloudy mixture immediately at room temperature. Secondary alcohols react within 3-

10 min. Primary alcohols require more than an hour to react. The chemical reaction involves replacing the OH group of the alcohol with a chloride ion from hydrochloric acid (HCl), forming an alkyl chloride. TOLLEN TEST Ag+ ions react with OH - of aqueous ammonia to produce a brown precipitate of Ag2O which is dissolved on addition of an excess of aqueous ammonia under the formation of [Ag(NH3)2]+. The silver diamine complex is reduced by glucose to metallic silver. Glucose is oxidized to gluconic acid. A silver mirror coats the flask because the Ag (I) ion is reduced to Ag(0) as Ag(I) oxidizes glucose to gluconic acid. Primary alcohol will be oxidized to aldehyde. And secondary will oxidized into ketone but tertiary alcohol gives no result where there no reaction occur. No silver mirror formation in the test tube that contain tertiary alcohol. CHROMIC ACID TEST Chromic acid (acidified dichromate, an oxidizing agent) can also be used to distinguish between types of alcohols by oxidizing the alcohol. Primary alcohols are oxidized to carboxylic acids, secondary alcohols are oxidized to ketones, and tertiary alcohols are not oxidized. During the oxidation, the orange-red color of the chromic acid changes to a bluegreen solution. In this experiment, an acidic sodium dichromate solution, which is orange in color and contains Cr6+, will be used to oxidize alcohols. As the alcohol is oxidized, the Cr6+ is reduced to Cr3+, which turns the solution a blue-to-green color. The appearance of this blueto-green color within one minute is considered a positive test for a primary or a secondary alcohol. Wear departmentally approved safety goggles when doing this experiment. All chemicals are potentially harmful. Prevent contact with your eyes, skin, and clothing. Avoid ingesting any of the reagents. If you spill any reagents, immediately notify your laboratory instructor. All the alcohols used are toxic and flammable. Do not perform the experiment near an open flame. Chromic acid reagent is toxic, corrosive, oxidant, and contains a suspected carcinogen. Acetone is flammable and irritating. Do not use acetone near an open flame. Lucas reagent (ZnCl2 in concentrated HCl) is toxic and corrosive.

Conclusion : Tertiary alcohol is more soluble in water compared with secondary and primary alcohol. It is because the branched alcohol (tertiary alcohol) provides higher solubility compared to unbranched alcohol (primary alcohol). It is due to the branch alkyl which have compact of hydrophobic group in tertiary alcohol. Primary alcohol will be oxidized to aldehyde. And secondary will oxidized into ketone but tertiary alcohol gives no result where there no reaction occur. So primary alcohol will formed silver mirror. Tertiary alcohols form a cloudy mixture immediately at room temperature. Secondary alcohols react within 3-10 minutes and Primary alcohols require more than an hour to react Primary alcohols are oxidized to carboxylic acids, secondary alcohols are oxidized to ketones, and tertiary alcohols are not oxidized Referrence: Saripah Salbiah Syed Abdul Azziz, Azmi Mohamed, Mohamad Saufi Rosmi, Nurul Aini bt Bakar, Mimi Marzziana Hamzah. Basic Organic Chemistry. Tanjung malim : Universiti Pendidikan Sultan Idris Achieved on 10 November 2011 from http://en.wikipedia.org/wiki/Alcohol Achieved on 10 November 2011 from http://www.chemguide.co.uk/organicprops/alcohols/background.html