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CHM301
ORGANIC CHEMISTRY II
Laboratory Experiment for Organic Chemistry
 REACTIONS OF ALCOHOLS, CARBONYLS AND ESTERS.

INTRODUCTION

Alcohols are classified as primary, secondary and tertiary, depending on whether the hydroxyl
group is attached to carbon that is bound to one, two or three other carbon atoms. Alcohols
treated with a particular reagent may differ in the rates that they react, or indeed even in the
type o product obtained, depending upon class to which they belong. Tests which distinguish
among the three classes, can be useful in determining the structure of unknown alcohol.

The typical structural formula and ketone are R-COH and R-COR respectively. Both of these
classes consist of the carbonyl group C=O. The carbon and oxygen atom are bonded with a
double bond. Due to the higher electronegativity of oxygen, the carbonyl group are polarized
with carbon atom having a slightly positive charge and oxygen atom a slightly negative charge.
The polarization of the carbonyl group has a strong influence towards the physical properties
and chemical properties of aldehyde and ketone.

The reaction of carboxylic acid and an alcohol produces an ester and water. The reaction is
catalysed with acid. Esters often have a fruity taste or odour. Octyl acetate prepared using
octanol as the alcohol, will remind you of oranges. You will prepare a compound which smells
like bananas.

OBJECTIVES

1. To study the reaction of alcohol and phenol.

APPARATUS

Test tubes, test tube rack, test tube holder, dropper, spatula, Bunsen burner, water bath,
heating mantle, reflux kit, separatory funnel, filter paper, vacuum filter, conical funnel,
distillation kit, steam bath, Erlenmeyer flask, boiling stone.
CHEMICALS

Ethanol, n-butyl alcohol-butyl alcohol, cyclohexanol, iso-amyl alcohol, phenol, 10% sodium
hydroxide, 2-propanol, orcinol, sodium metal, indicator, benzyl alcohol, t-butyl alcohol,
cholesterol, resorcinol, chromic acid, Lucas reagent, bromine water, ferric chloride, methanal,
ethanal, propanone, Tollens reagent, KMnO4, Schiff regent, Fehling A and B, 2,4-DNPH,
isopentyl alcohol, glacial acetic acid, concentrated H2SO4, 5% sodium bicarbonate, saturated
sodium chloride, anhydrous sodium sulphate.

DISCUSSION

In your discussion, you need to include equations of each reaction in the experiment above.
State your observation and give the conclusion of your results. If the observation does not
comply with your expectation, you need to give the reason and expected results of the
experiment. Answer each question given in the procedure above. Write discussion in proper
arrangement.
 A. REACTION OF ALCOHOL AND PHENOL

A.1 Solubility

In six separate test tubes place 0.5mL or 0.2-0.5g of each the following: ethanol, n- butyl
alcohol, t-butyl alcohol, cyclohexanol, iso-amyl alcohol and phenol. (Caution: Avoid any skin
contact with phenol). In case of burn, wash thoroughly with water for 15 minutes and notify
your instructor). Add 2mL of water to each test tube, mix and observe. Record your
observations.

A.2 Reaction with metallic sodium

Place 2mL of each of the following in separate dry test tubes: ethanol, 1-propanol, 2-propanol
and orcinol. Add a small piece sodium metal into each test tube and note the result. Add few
drops of universal indicator to the solution and record the result. (Caution: DO NOT discard
the contents of any tube with unreacted sodium down the drain, sodium reacts violently with
water. Add sufficient ethanol to destroy any unreacted sodium, and then rinse the solution
down the drain).

A.3 Tests for the three classes of alcohols

The Lucas Test

Place 2 mL of Lucas reagent in each of six test tubes. Add about five drops of the alcohol to
be tested, shake and note the length of time it takes for the mixture to become cloudy or
separate into two layers. Test 1-butanol, 2-butanol, cyclohexanol, n-amyl alcohol, benzyl
alcohol and t-butyl alcohol and record the results.

Chromic Acid Oxidation

Place 1mL of acetone in each of five separate test tubes. To each test tubes, add one drop of
a liquid alcohol or a few crystals (10mg) of a solid alcohol to be tested and shake until the
solution is clear. Then add, with shaking, one drop of the reagent. Test the following alcohols:
1-butanol, 2-buanol, t-butyl alcohol, n-amyl alcohol and benzyl alcohol.

A.4 Reaction of phenols

With Bromine water

About 0.1g of phenol is dissolved in 3mL of water add bromine water with shaking, until the
yellow colour persists. Observe the results.
With Ferric Chloride

In three separate test tubes dissolve one or two crystals, or one or two drops of the compounds
to be tested in 5mL of water. To each test tube, add one or two drops of 1% ferric chloride
solution, shake and observe the results. Test phenol, resorcinol and 2-propanol and record
the results.

QUESTIONS

1. Select one compound from the following pairs of compounds which is more water
soluble. Explain you answer.
a) Ethanol and 1-hexanol
b) 1-propanol and1,2,3-propanetriol

2. Suggest a chemical test(s) to distinguish the following pairs of compounds. Include the
reagent, reaction conditions and observations. Write the equation involved.
a) 1-butanol and2-butanol
b) Phenol and phenylethanol

3. What is Lucas reagent made of?

B.1 Reaction of methanal

1. Into 5mL of Tollen’s reagent in a test tube, add 2mL of methanal. Shake the solution and
warm it in a bath of warm water.
2. Into 5mL of KMnO4 solution in a test tube add few drops of dilute sulfuric acid. Then add
2mL of methanal.

B.2 Reaction of ethanal

1. Into 1mL of Schiff reagent in a test tube, add few drops of ethanal.
2. Into 5mL of Tollen’s reagent in a test tube, add 5mL of ethanal. Shake the solution and
warm in a bath of warm water.
3. Into a mixture of 3mL of Fehling A solution and Fehling B solution, add few drops of ethanal.
Warm the mixture in a boiling water bath.
4. Into 5mL of KMnO4 solution in a test tube add few drops of dilute sulfuric acid. Then add
few drops of ethanal.
5. Into 3 to 5 drops of ethanal in a test tube, add 3mL of 2,4-dinitrophenyl hydrazine. Heat the
mixture slowly and carefully with a Bunsen burner and then cool it.

B.3 Reaction of propanone

1. Into 5mL of Tollen’s reagent in a test tube, add 5 drops of propanone. Shake the solution
and warm it in a bath of warm water.
2. Into a mixture of 3mL of Fehling A solution and Fehling B solution, add few drops of
propanone. Warm the mixture in a boiling water bath.
3. Into 5mL of KMnO4 solution in a test tube add few drops of dilute sulfuric acid. Then add
few drops of acetone. Leave the solutions for few minutes.
4. Into 3 to 5 drops of propanone in a test tube, add 3mL of 2,4-dinitrophenyl hydrazine. Leave
the mixture for few minutes.

QUESTIONS

1. What is your observation if you differentiate 2-butanone and 2-methylbutanal using

1. Place 15mL (12.2g, 0.138mol) of isopentyl alcohol in a 100mL round bottom flask and add
20mL of glacial acetic acid.
2. Switch the flask and carefully add 4mL of concentrated H2SO4 (CAUTION: highly corrosive).
3. Attach a reflux condenser and using a heating mantel, reflux the mixture for 1 hour (do not
forget to add boiling stones). Cool to room temperature.
4. Place the reaction mixture in separatory funnel and add 55mL of cold water (remember to
rinse the reaction flask with 10mL of cold water and add it to the separatory funnel).
Separate the lower aqueous layer.
5. extract the organic layer with 25mL of 5% sodium bicarbonate solution twice (test to be
certain that the aqueous layer is basic to litmus paper otherwise wash again). CAUTION:
formation of carbon dioxide which will exert pressure inside the separatory funnel.
6. Extract the organic layer with 25mL water. Finally, add 5mL of saturated aqueous sodium
chloride to aid in layer separation (it removes traces of water from the organic layer). Do
not shake the solution but simply swirl. Draw off the lower aqueous layer. Pour the top
organic layer into conical flask and dry with 2g of anhydrous magnesium sulphate.
7. Decant the ester into distilling flask (make sure that the dry agent is excluded and all
glassware completely dry). Set up the distillation apparatus as described by your instructor.
Be certain that adapter is open to the atmosphere ad your thermometer is place correctly
in the distilling head (do not forget the boiling stones). Collect all distilled material but collect
the fraction between 134oC and 143oC in separate tared flask. Keep the receiver flask cold
to reduce the vapor escaping into the lab environment. Never distil to dryness. Weight the
product and calculate the percent yield.

QUESTIONS

1. What is the purpose of extracting the organic layer with 5% aqueous sodium
bicarbonate? Remember, you used an excess off glacial acetic acid.

2. What is the purpose of extracting with 25mL of water?

A. REACTION OF ALCOHOL AND PHENOL

Reaction of alcohol

Test Observation

a. Solubility
i. ethanol

ii. n-butyl alcohol

iii. t-butyl alcohol

iv. cyclohexanol

v. iso-amyl alcohol

vi. phenol

b. Reaction with metallic sodium

ii. 1-propanol

iii. 2-propanol

iv. Orcinol

c. Lucas test
i. 1-butanol

ii. 2-butanol

iii. Cyclohexanol

iv. n-amyl alcohol

v. benzyl alcohol

vi. t-butyl alcohol

ii 2-butanol

iii t-butyl alcohol

iv n-amyl alcohol

v benzyl alcohol

vi cholesterol

Reaction of phenol

Test Observation

a. Bromine water

b. Ferric chloride
i. phenol

ii. resorcinol

iii. 2-propanol
 DATASHEET

B. REACTIONS OF ALDEHYDE AND KETONE

Observation
Test
Methanal Ethanal Propanone

Tollen’s test

Fehling’s test

Schiff reagent

Reaction with KMnO4

Condensation with 2,4-DNPH

C. SYNTHESIS OF ISOPENTYL ACETATE (BANANA OIL)

1. Mass of product: ______________________________________