SEMESTER I

SESSION 2010/2011

DEPARTMENT OF CHEMISTRY

FACULTY OF SCIENCE & MATHEMATICS

UNIVERSITI PENDIDIKAN SULTAN IDRIS

TKO 1013
BASIC ORGANIC CHEMISTRY

LABORATORY M ANUAL
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STUDENT’S NAME
LECTURER’S NAME DR SARIPAH SALBIAH SYED ABD. AZIZ
MATRIC NO
DATE/DAY/TIME
LABORATORY
 Department of Chemistry
Faculty of Science and Mathematics
Universiti Pendidikan Sultan Idris

Organic Chemistry Laboratory Safety Rules

1. Each experiment must be conducted with the presence of laboratory

instructor. Do not attempt unauthorized experiments.

2. First Aid each laboratory has a small First Aid Kit. Report all
injuries, no matter how minor, to your instructor.

3. Eating and drinking are forbidden in the laboratories.

4. Eye protection must be worn at all times. Users of contact

lenses should be aware that vapours will be absorbed by the lens
and may lead to severe irritation and damage to the cornea if not
dealt with promptly.

5. The wearing of laboratory coat is compulsory. Appropriate footwear

is required. Sandals, slip-ons and open-toed shoes are not
permitted in the laboratory as they do not provide sufficient
protection against broken glass or chemical spills, or may prevent
quick movements if needed in an emergency.

6. Protective gloves should be used when necessary.

7. All dangerous or odorous experiments must be done in a fumehood.

All experiments requiring an overnight, or longer, reaction time
should also be carried out in a fumehood. In such a case, the
experiment should be clearly labelled with a self-adhesive label.

8. If you have any doubt as to the safety of a given operation, consult

your instructor.

9. A chemical laboratory is a hazardous environment. A little careless

could leave you or other students disabled for life. Do everything
you can to ensure your own safety and that of others. Maintain a
clean and uncluttered working area. Each student is responsible for
leaving the bench and adjacent sink clean and tidy. Even tiny
amounts of corrosive chemicals can cause ulcerated burns so
immediately clean up any spill, no matter how minor.

10.Minimize your exposure to organic vapours and other noxious gases

by using fumehood. Above all, be safety-conscious every minute
you spend in the laboratories.

11.Keep bench and floor clean.

12.Before leaving the laboratory, be sure that the water, steam,

heaters, and gas cocks are shut off.
 Experiment 1

Molecular Modeling

Objective:

Upon completion of this experiment, students should have learned:

1. Ball and stick model of molecules construction

2. Potential energy diagram

Introduction

Since the beginnings of organic chemistry, somewhere in the middle

of the nineteenth century, chemists have sought to visualize a three
dimensional characteristics of the all-but-invisible molecules, which
participate in chemical reactions. The concrete models, which could
be held in the hand, were developed. Many kinds of model sets,
such as framework, ball-and-stick, and space-filling designed and
devised to allow people to visualize the spatial and directional
relationships within molecules (atoms). These hand-held models
were interactive, and they could be readily manipulated in space.

Apparatus

Ball and stick model

Reagent
-

procedure

A. Methane

1. Construct a model of methane.

2. Place them on the bench and observe. Draw the three-
dimensional structural of the methane.
3. What is the bond angle between H-C-H ?

B. Ethane, Propane and Butane

1. Construct and draw Sawhorse and Newman projections formula

for molecule below:

a. Ethane: The staggered and eclipsed conformations. Which

conformation are the more stable? Why?

b. Propane: The staggered and eclipsed conformations. Which

conformation are the more stable? Why?
c. Butane: The anti or gauche conformations are more
stable? Why?
C. 2-Methylpropane

1. Construct a model of 2-methylpropane.

2. View through C2-C3, and draw all staggered and eclipsed
conformations by rotating 60º of the C2-C3 bond.
3. Which conformation is the most stable and most unstable?

D. 2, 3-Dimethylbutane

1. Construct a model of 2, 3-dimethylbutane.

2. View through C2-C3, and draw all the staggered and eclipsed
conformations by rotating 60º of the C2-C3 bond.
3. Which conformations are the most and the most unstable?

E. Potential Energy Diagram

1. Construct and draw Newman projection formula for

the molecule below.
a. Ethane
b. Propane

2. View through C1-C2, and draw all the staggered and eclipsed
conformations by rotating 60º of C1-C2 bond.
3. Sketch the complete potential energy diagram for each molecule
(0-360º).

F. Optical isomerism

By using the molecular model, draw all the structures of the

molecule and answer all the questions.

1. a) Does compound with no plane of symmetry optically

active? Explain why and why not.
b) Compound with stereogenic carbon (chiral carbon) does
not possess a plane of symmetry, true or false, construct
and draw an example of the symmetrical compound with
stereogenic carbon.

2. By using the molecular models, determine the absolute

configuration (R or S) for each of the following molecules.

F COOH

a) Cl H b) H NH2

Br CH3
 OH CH3

c) Br CH3 c) HOH2C CH(CH2)3

CH3 CH3

CH3
CH
e) H H Cl
3
Br OH f)
CH2CH3

CH3 Cl H
CH3

3. Construct the molecular models for the following molecules

and draw their mirror image. Determine whether the object
and its mirror image were identical or a pair of enantiomer.
Which compound is unsymmetrical (optically active)?

H OCH3

a) Br H b) H OH

CH3 Cl
CH3 CH3

H OH HO H
H OH H OH
c) d)

CH3 CH3
 EXPERIMENT 2

Cis-Trans Isomers

Objective

Upon compilation of this experiment, students should have learned:

Introduction

Maleic acid and fumaric acid have the same molecular formula:
C4H4O4. Each compound contains two carboxyl groups, -COOH, and
a double bond. The compounds are isomers because their structures
differ in the geometry, or arrangement in space of the atoms in the
molecule. Examine the structural formulas of the two acids shown
below and note that in the trans form the same side. In fact that
isomers can be isolated that indicates that rotation of the molecule
at the double bond is restricted.

HOOC COOH HOOC H

H H H COOH

cis isomer trans isomer

As a result of this geometrical difference, the cis and trans isomers

have physical properties. In addition, some of their chemical
properties differ because of the location of the two carboxyl groups.

In this experiment you will convert maleic acid to fumaric acid by

heating it in concentrated hydrochloric acid (HCl). You also will
compare some of the properties of each acid and attempt to explain
any differences in term of structures. This should enable you to
draw some conclusions about which acid, maleic or fumaric, is the
trans and the cis form.

Apparatus

125 mL Erlenmeyer flask, wath glass, 100 mL beaker, test tubes,

filter paper, and melting point apparatus.

Reagent

Maleic acid, fumaric acid, concentrated hydrochloric acid (12M),

magnesium ribbon (3cm strip), sodium carbonate, pH paper.
Procedure

CAUTION: Concentrated hydrochloric acid (HCl) cause severe skin

burn. Immediately wash the affected areas with cold running water
and promptly report the accident to your instructor.

Part A: Conversion of maleic acid to Fumaric acid

1. Weight 2.0g of maleic acid in a clean, dry 125mL Erlenmeyer

flask. Add 4 mL distilled water and warm slightly to dissolve
the acid.

2. Add 5mL of concentrated hydrochloric acid (HCl) and insert a

plastic air condenser.

3. Place the flask in hot water bath assembly.

4. Heat until solid of fumaric acid form in the flask

(approximately 5 minutes).Cool the solution to room
temperature by slowly placing the Erlenmeyer flask into a
water bath.

5. Pour the contents into a 100 mL beaker. Allow the crystal to

settle; then carefully decent and discard the supernatant
liquid.

6. Rinse any remaining crystal in the Erlenmeyer flask with

approximately 10 mL of cold distilled water pour them into the
beaker. Again decent and discard the supernatant liquid.

7. Using two additional 5 mL portion of cold distilled water,

repeat the washing procedure.

8. Dry the crystals of fumaric acid. Get the weight and calculate
the percentage of the yield. Determine the melting point of
your product and also melting point of maleic acid.

Part B: Comparison of Two Isomers

Solubility

1. Place 0.1g of each into separate test tubes. Add 2mL distilled
water to each and make a qualitative comparison of solubility.

2. Record your observation on your report sheet.

Chemical properties

1. Prepare solution of each acid by adding 0.1g maleic acid and

0.1 fumaric acid into a beaker containing 20mL distilled water,
respectively.
2. Place 5mL for each solution into 3 different test tubes and
perform each of the following tests on one solution each of
maleic and fumaric acids.

a. Estimate the hydrogen ion concentration by testing one

solution of each acid with pH paper

b. To another solution of the acid, add a small amount of

sodium carbonate.

c. To the third solution of the acid, add 3cm strip of

magnesium ribbons.

3. After each test, compare and record the results on the report
sheet in a table form.
 Experiment 3

Hydrocarbons

Objective

Upon compilation of this experiment, student should have learned:

1. Some reactions of hydrocarbon

2. Chemical and physical properties of hydrocarbon
3. Comparison of different classes in hydrocarbon

Introduction

Qualitative organic analysis is for identification and characterization

of unknown compounds, is an important part of organic chemistry.
Every chemist must learn the appropriate methods for establishing
for establishing the identification of a compound. In this
experiment, you will be issued an unknown compound and will be
asked to identify it through chemical methods.

With a general unknown, you must first determine the class of

compound to which the unknown belongs, that is, identify its main
functional group; then you must determine the specific compound in
that corresponds to the unknown.

Apparatus

1) Alkanes Reactions

A. Ignition Test

1. Place a small amount of heptane on a spatula and place it in

the flame of a Bunsen burner.
2. Observe whether a sooty flame result.

B. Bromine Test

1. Place a small amount of 0.5% bromine in CCl4 in two test

tubes (labelled as A and B).
2. Add 5-10 drops of heptane in both test tubes and shake them
well.
3. For the test tube A, store it in the dark room (cabinet). For
test tube B, expose it to the sunlight.
4. Record your observations after 30 minutes.
 C. Baeyer Test

1. Slowly add an aqueous solution of KMnO4 drop while shaking

to 0.5 of mL heptane.
2. Observe any colour of the reagent, usually within 1 minute.

D. Sulphuric Acid Test

1. Slowly add 3-4 drops of heptane to 5drops of H2SO4 in the

test tube.
2. Record any color change.

2)Alkenes Reactions

A. Ignition Test

1. Place a small amount of cyclohexene on a spatula and place it

in the flame of a Bunsen burner.
2. Observe whether sooty flame result.

B. Bromine Test

1. Place 10 drops bromine in CCl4 in two test tubes (labelled as A

and B).
2. Add 5-10 drops of cyclohexene in both test tube and shake
well.
3. For test tube A, store it in the dark room (cabinet). For test
tube B, expose to the sunlight.
4. Record your observations after 30 minutes.

C. Baeyer Test

1. Slowly add an aqueous solution of KMnO4 drop while shaking

to 0.5 mL of heptane.
2. Observe the color of the reagent, usually within 1 minute.

D. Sulphuric Acid Test

1. Slowly add 0.5 mL of cyclohexene to 1 mL of H2SO4 in the test

tube.
2. Record any color changes.
3. Alkynes Reactions

A. Bromine Test

1. Trap acetylene gas in a test tube.

2. Place 5 drops of bromine solution in a test tube and shakes it
well.
3. Record your observations after 30 minutes.

B. Bayer Test

1. Trap acetylene gas in a test tube.

2. Place 5 drops of an aqueous solution of KMnO4 in a test tube
and shakes it well.
3. Observe the color of the reagent usually within 1 minute.
 Experiment 4

Alcohol

Objectives

Upon completion of this experiment, the students should have

learned:

1. The chemical tests to identify the existence of alcohol

2. differentiation of different class of compound

introduction

the first step in the process of successfully identifying an unknown

organic compound is to determine what functional groups are
present or absent in the unknown. One method is to use as a
careful observation of result chemical reactions. In this experiment,
you will perform a series of chemical tests on known compounds
that have different functional groups. You will carefully note
changes during the reaction and record the result for both positive
and negative test.

Then you will develop a flow scheme that can be used to distinguish
between an aldehyde, a ketone, an alcohol, a phenol, a carboxylic
acid and 2-methyl-2-pentanol.

Apparatus

Test tubes, droppers and hot plate.

Reagent

Liquid compounds, distilled water, 1-hexanol, 4-methyl-2-pentanol,

2-methyl-2-pentanol, Lucas reagent, NaOH, AgNO3, NH3, acetone
and chromic acid.

Procedure

A. solubility Test

1. Place 5 drops of a liquid compound in a small test tube.

2. Add 10 drops of distilled water and fix the rubber stopper. Then
shake it well. Determine whether the mixture partial, completely
soluble or insoluble.

3. record your observation.

B. lucas Test

1. Run this test only on 1-hexanol, 4-methyl-2-pentanol and 2-

methyl-2-pentanol.

2. Label three dry test tubes (A,B and C) and to the test tube A,
add 3 drop of 1-hexanol.

3. in a similar manner, add 3 drops of other alcohols to the other

test tubes.

4. add 10 drops of Lucas reagent to each of the test tube.

5. Swirl rapidly and observe closely for the formation of cloudiness

for at least 10 minutes.

6. Record the time it takes for the homogenous solution to turn

cloudy.

C. Tollens Test

1. Make sure that the test tubes to be used in this test are very
clean. The test tubes may be cleaned by rising with 10% NaOH.

2. Add 1 mL of 5% AgNO3 and 1 drop of 10% NaOH.

3. Add concentrated aqueous NH3 drop wise, and shaking, until the
precipitate formed just dissolves.

4. Add 1 drop of liquid compound or 20 mg of solid compound.

Swirl the test tube, then let stand for 10 minutes.

5. If no reaction occurred, heat test tube in a beaker of warm water

for a few minutes.

6. A positive test is the formation of silver mirror coating on the

side of the test tube.

7. Dispose the product by cautiously adding dilute nitric acid to the

silver mirror. Then, wash it down the drain with lots of running
water.

D. Chromic Acid Test

1. In a small test tube, place 2 drops of liquid compound or 20 mg

of solid compound (dissolve the solid compound in about 5 drops
of acetone).

2. Add 1 drop of chromic acid solution. Observe carefully.

3. A positive reaction occurrence of a precipitate, its color and time

it took to form precipitate.
Question

1. Write the complete chemical equations for the liquid compound

that gave the positive test in Lucas test, Tollens and chromic acid
test.
 Experiment 5

Aldehydes and Ketones

Objective

Upon completion of this experiment, the students should have

learned:

1. Chemical tests to determine the existence of aldehyde and

ketone

2. differentiation between aldehyde and ketones

Introduction

Aldehydes and ketones, compounds containing the carbonyl

functional group C=O,

where it has only hydrogen atoms and alkyl groups as substituents,

are called aldehydes RCHO or ketones RCOR’. The chemistry of
these compounds is primarily due to the chemistry of the carbonyl
functional groups. These compounds indentified by the distinctive
reactions of the carbonyl function.

Apparatus

Test tubes, droppers, glass rod and hotplate.

Reagents

Liquid compounds, ethanol, 2,4-DNPH reagent, 2-pentanone, 3-

pentanone, distilled water, NaOH, AgNO3, iodine-potassium iodide
solution, nitric acid and chromic acid.

Procedure

A. 2,4-Dinitrophenylhydrazine Test

1. In a small test tube, add 1 drop of liquid compound or 20 mg of

a solid compound (dissolve the solid compound in 5 drops of
ethanol).

2. To the solution add 7-8 drops of 2,4-DNPH reagent.

3. Stir with a glass rod.

4. A positive test is the formation of a yellow, orange or red

precipitate. However, some compounds will require up to 15
minutes, or even gentle heating.
B. Iodoform Test

1. Label two small test tubes (A & B).

2. In test tube A, add 2 drops of 2-pentanone.

3. In test tube B, add 2 drops of 3-pentanone.

4. To each test tube, add 1mL distilled water. Swirl vigorously to

dissolve.

5. To each test tube, add 1mL of 10% NaOH and 1.5mL of 5M

iodine-potassium iodide solution.

6. A positive test is the disappearance of the brown color and the

formation of a yellow precipitate.

C. Tollens Test

1. Make sure that the test tubes to be used in this test are very
clean. The test tubes may be cleaned by rising with 10% NaOH.

2. Add 1mL of 5% AgNO3 and 1 drop of 10% NaOH.

3. Add concentrated aqueous NH3 drop wise, with shaking, until the
precipitate formed is dissolved.

4. Add 1 drop of liquid compound or 20 mg of solid compound.

Swirl the test tube, and let it stand for 10 minutes.

5. If no reaction occurs, heat the test tube in a beaker of warm

water for a few minutes.

6. A positive test is formation of a silver mirror coating on the test

tube.

7. Dispose the products by cautiously adding dilute nitric acid to the

silver mirror. Then, wash it down the drain with lots of running
water.

D. chromic acid Test

1. In a small test tube, place 2 drops of a liquid compound or 20

mg of a solid compound (dissolve the solid compound in about 5
drop of acetone).

2. Add 1 drop of chromic acid solution. Observe carefully.

3. A positive reaction is the occurrence of precipitate. Observe its

color and the time it took to form the precipitate.
Question

1. Write the complete chemical equation for liquid compound

that the positive test in 2,4-Dinitrophenylhydrazine, iodoform
and chromic acid test.
 Experiment 6

Carboxylic Acids and Derivatives

Objectives

Upon completion of this experiment, the student should have

learned:

1. Some reactions of carboxylic acids.

2. Some qualitative test for carboxylic acids.

Introduction

Carboxylic acids and their derivatives are compound, in which a

carbonyl carbon atom is bonded to an atom or group of atom other
than carbon or hydrogen.

O O O O

R C R C R C R C

Substituent OH OR’ Cl

Acid derivative carboxylic acid ester acid chloride

Acid have a hydroxyl group, esters have an alkoxy group, and acid
chlorides bonded to the carbon atom. Since these compounds are
structurally related, they are interconvertible by appropriate
substitution reactions.

Carboxylic acids form hydrogen bonds with water and are soluble
providing the alkyl group is not too large. Carboxylic acids are weak
acids and are slightly ionized in water. However, reaction with
sodium hydroxide converts carboxylic acids because they are more
soluble than the carboxylic acids because they are ionic.

O O

R C + NaOH R C + Na+ + H2O

OH O
Carboxylic acids react with alcohols in the presence of a strong
acids as catalyst to form esters. The esterification is favoured by
increased the concentrations of one or both of the reactants.

O O
H3O+
R C + R’OH R C + Na+ + H2O

OH O

An ester can be cleaved into its component carboxylic acid and

alcohol by the reversal of the reaction above in excess of water.
However, the reaction is made essentially quantitative by adding
molar amounts of strong base. This reaction, called saponification,
result in the formation of an alcohol and a carboxylate salt.

O O

R C + NaOH R C +Na + Na+ + R’OH

OR’ O-

Acid chlorides are extremely reactive compounds that to react

replace the chlorine atoms by substitution. Reaction with water
result in the formation of an acid, where as

O O

R C + H2O R C + HCl

Cl OH

O O

R C + ROH R C + HCl

Cl OR

Apparatus

Test tubes, droppers, hot plate, reflux condenser, round bottomed

flask and beaker.

Reagent

Acetic acid, benzoic acid, salicylic acid, methanol, absolute ethanol,

ethyl benzoate, 3 M sodium hydroxide, concentrated sulphuric acid,
solid sodium hydroxide and litmus paper.
Procedure

Part A: solubility of Carboxylic Acids

1. Determine the solubility of acetic acid and salicylic acid, one at a

time in each of these solvents: water ethanol and 3 M NaOH
solution.

2. Add 6 drops of the acid to 3mL of the solvent in a clean test

tube.

3. Shake the test tube.

4. If the acid dissolves, continue dropwise addition no more of the

acid dissolves or until the total volume reached 4 mL.

5. Classify the acid either it is soluble, slightly soluble or insoluble.

6. Record your observations.

7. Repeat the solubility test with benzoic acid and salicylic acid, but
use smaller amount of the compound.

8. Dissolve 0.1 of the compound in 10 mL of water by heating the

solution (use water bath).

CAUTION: Ethanol is flammable. Make sure that your ethanol

solvent used earlier is in a stoppered container and is
distance from the burner.

Part B: Estirification

CAUTION: Sulfuric acid is strong corrosive acid that will

cause severse skin burns. Immediately wash any affected
areas with large quantities of water. Notify your instructor
and seek medical evaluation of the chemical burn.

Part A: Aster A

1. Pour 1 mL of acetic acid and 1 mL of ethanol into a clean test

tube.

2. Add about 4 drops of concentrated sulfuric acid carefully, and

mix.

3. Stand the tube in a beaker of hot water at about 800C for 10

minutes.

4. Record your observation and write the equation for the

reaction.
Part B: Ester B

1. Gently warm a test tube containing 1 g of salicylic acid, 2 mL

of methanol, and 4 drops of concentrated sulphuric acid.

2. After a few minutes and allow the mixture to cool. Note that
the odor is sometimes more apparent if the liquid is poured
into about 25 mL of cold water.

3. Record your observation and the equation for the reaction.

Part C: Saponification of an ester

CAUTION: Sodium hydroxide is a caustic substance. Do not

touch this substance. Rinse your skin with water
immediately if it has a soapy feeling. Sodium hydroxide will
cause irreversible eye damage and blindness. Clean up any
spilled material at once.

1. In a round bottomed flask, mix 5 mL of ethyl benzoate with a

solution of 3 g of sodium hydroxide in 15 mL of water.

2. Fit the flask with a reflux condenser as shown in figure below.

3. Place a few boiling chips are in the flask to prevent bumping.

4. Boil the mixture gently for at least 15 minutes or until ester layer
has disappeared.

Apparatus for refluxing a liquid

5. Cool the flask.

6. Then, dilute the contents with about 50 mL of water.

7. Separate the aqueous layer from the oily layer using a
separation funnel.

8. While stirring, add dilute hydrochloride acid to the aqueous layer

until the solution is acidic to litmus paper.

9. Filter the precipitate and allowing the solution to cool.

10.Collect the solid by suction, and compare its appearance with

that of the benzoic acid from part A.

11.Record your observation and equation for the saponication of

ethyl benzoate.

Questions

Write the products from the following reactions.

a. C + CH3CH2OH

OH
O

b.CH3(CH2)5CH2 C + KOH

OCH(CH3)2

Cl
O

c. C + H2O

Cl

O O

d. C C + H2O

Cl
Cl

O O

e. C C + H2O

Cl
CH3