Name ______________________ Date Performed______________

Course & Year _______________ Score _____________________

Laboratory Exercise No.1

Drawing Lewis Structure

Introduction

Lewis structure is used to represent the covalent bonding of a molecule or ion. Covalent bonds
are a type of chemical bonding formed by the sharing of electrons in the valence shells of the
atoms. Covalent bonds are stronger than the electrostatic interactions of ionic bonds, but keep
in mind that we are not considering ionic compounds as we go through this chapter. Most
bonding is not purely covalent, but is polar covalent (unequal sharing) based on
electronegativity differences.

The atoms in a Lewis structure tend to share electrons so that each atom has eight electrons
(the octet rule). The octet rule states that an atom in a molecule will be stable when there are
eight electrons in its outer shell (with the exception of hydrogen, in which the outer shell is
satisfied with two electrons). Lewis structures display the electrons of the outer shells because
these are the ones that participate in making chemical bonds.

We will use molecules (CO2, CO32-, NH4+ , PF5 and BF3) as our examples of a simple method for
drawing Lewis dot structures. While this algorithm may not work in all cases, it should be
adequate the vast majority of the time.

Lewis Structure for Neutral Molecules

Steps

1. Decide how many valence (outer shell) electrons are possessed by each atom in the
molecule.

2. If there is more than one atom type in the molecule, put the most metallic or least
electronegative atom in the center. Recall that electronegativity decreases as atom moves
further away from fluorine on the periodic chart.
 Arrangement of atoms in CO2:

3. Arrange the electrons so that each atom contributes one electron to a single bond between
each atom.

4. Count the electrons around each atom: are the octets complete? If so, your Lewis dot
structure is complete.

5. If the octets are incomplete, and more electrons remain to be shared, move one electron per
bond per atom to make another bond. Note that in some structures there will be open octets
(example: the B of BF3), or atoms which have ten electrons (example: the S of SF5).

6. Repeat steps 4 and 5 as needed until all octets are full.

7. Redraw the dots so that electrons on any given atom are in pairs wherever possible.
Lewis Structure for Negatively Charged Ions (CO32-)

Steps

1. Use the same procedure as outlined above, then as a last step add one electron per
negative charge to fill octets.  Carbonate ion has a 2- charge, so we have two electrons
available to fill octets.

Using the procedure above, we arrive at this structure: 

2. The two singly-bonded oxygen atoms each have an open octet, so we add one electron
to each so as to fill these octets.  The added electrons are shown with arrows. 
3. Don't forget to assign formal charges as well!  The final Lewis structure for carbonate ion
is:

Lewis Structure for Positively Charged Ions (NH4+)

Steps

1. Use the same procedure as outlined above, then remove one electron per positive
charge as needed to avoid expanded octets.  When using this procedure for positively
charged ions, it may be necessary to have some atoms with expanded octets (nitrogen
in this example).  For each unit of positive charge on the ion remove on electron from
these expanded octets.  If done correctly, your final structure should have no first or
second period elements with expanded octets.

2. Using the basic procedure outlined above, we arrive at a structure in which nitrogen has
nine valence electrons.  (Electrons supplied by hydrogen are red; electrons supplied by
nitrogen are black.)  Removal of one of these valence electrons to account for the 1+
charge of ammonium ion solves this octet rule violation.
Lewis Structures for Electron-rich Compounds, PF5.

Elements with atomic number greater than 13 often form compounds or polyatomic ions in
which there are “extra” electrons. For these compounds we proceed as above. Once all of the
octets are satisfied, the extra electrons are assigned to the central atom either as lone pairs or
an increase in the number of bonds. (Never use multiple bonds with these compounds—you
already have too many electrons.)

Steps

1. The electronegativity of fluorine is greater than that of phosphorus—so the phosphorus

atom is placed in the center of the molecule.

2. The total number of electros is 40 [5(7 from each fluorine) + 5 from the phosphorus] =
40. Using a single bond between the phosphorus atom and each of the fluorine atoms
and filling the remaining electrons to satisfy the octet rule for the fluorine atoms accounts
for all 40 electrons. Note that there are five bonds around the central atom.

Lewis Structures for Electron-poor Compounds, BF3.

There is another type of molecule or polyatomic ion in which there is an electron deficiency of
one or more electrons needed to satisfy the octets of all the atoms. In these cases, the more
electronegative atoms are assigned as many electrons to complete those octets first and then
the deficiency is assigned to the central atom.
Steps
1. The electronegativity of fluorine is greater than that of boron—so the boron atom is
placed in the center of the molecule.

2. The total number of electron is 24 [3(7 from each fluorine) + 3 from boron] = 24. Using a
single bond between the boron and each of the fluorine atoms and filling the remaining
electron as lone pairs around the fluorine atoms to satisfy the octets accounts for all 24
electrons.

3. The boron atom is two electrons shy of its octet. You may ask about the formation of a
double bond (and even resonance). But, fluorine and boron are not in the list that can
form double bonds (C, N, O, P, S) and so the compound is electron poor.

Formal Charge

The charge on each atom in a molecule is called the formal charge. The formal charge can be
calculated if the electrons in the bonds of the molecule are equally shared between atoms. This
is not the same thing as the net charge of the ion.

In calculating formal charge, the following steps can be extremely helpful:

1. Determine the number of valence electrons that should be present for each atom in the
structure.
2. Count the electrons around each atom in the structure (each lone pair = 2 electrons,
each single bond =1 electron, each double bond = 2 electrons, each triple bond = 3
electrons).
3. Subtract the number of valence electrons that should be present (from step 1) from the
electrons counted in step 2 for each atom. This is the formal charge for each atom.
4. Check that the formal charges add up to equal the overall charge of the molecule.
 Formal charge = (number of valence electrons) - (number of non-bonding electrons + 1/2
number of bonding electrons) 

In Lewis structures, the most favourable structure has the smallest formal charge for the atoms,
and negative formal charges tend to come from more electronegative atoms.

An example of determining formal charge can be seen below with the nitrate ion, NO3-:

1. The double bonded O atom has 6 electrons: 4 non-bonding and 2 bonding (one electron
for each bond). Since O should have 6 electrons, the formal charge is 0.
2. The two singly bonded O atoms each have 7 electrons: 6 non-bonding and 1 bonding
electron. Since O should have 6 electrons, and there is one extra electron, those O
atoms each have formal charges of -1.
3. The N atom has 4 electrons: 4 bonding and 0 non-bonding electrons. Since N should
have 5 electrons and there are only 4 electrons for this N, the N atom has a formal
charge of +1.
4. The charges add up to the overall charge of the ion. 0 + (-1) + (-1) + 1 = -1. Thus, these
charges are correct, as the overall charge of nitrate is -1.

Objectives

1. Draw Lewis structure of simple inorganic and organic molecules.

2. Calculate the formal charge of each atom in the structure.

Materials

Pen, paper, periodic table

Procedure

1. Draw the Lewis structure of the following molecules by following the suggested steps.
2. Identify the formal charges of each atom in the structure except hydrogen.

a. Sulfur dioxide (SO2)

b. Carbonate ion ( CO32-)
c. Dibromomethane( CH2Br2)
d. Nitrogen trichloride (NCl3)
e. Hypochlorite ion (ClO-)
f. Acetylene C2H2
g. Ozone (O3)
Result and Discussion
Conclusion
Name ______________________ Date Performed______________
Course & Year _______________ Score _____________________

Laboratory Exercise No.2

Separation and Purification of Organic Compounds

Introduction

The separation and purification of organic compounds from impurities are important laboratory
procedure before determining their purity and qualitative analysis for elements present in
organic compounds. Organic compound prepared in the laboratory are usually contaminated
with other organic substances or impurities due to side organic reactions that yield substances
other than the desired product. In addition, the organic compounds have the tendency to
undergo partial decomposition or rearrangement upon standing or when exposed to heat and
light. The different methods of purification and separation are : solution and filtration,
crystallization, decolorization, sublimation, extraction, distillation, chromatography, dialysis, and
electrophoresis.

Objectives

1. Separate organic compounds from mixture.

2. Purify organic compounds using different methods.
3. Describe the different methods of purifying and separating organic mixtures.

Materials

Naphthalene platform balance

Brown sugar mortar & pestle
Ethyl alcohol test tubes
Urea or benzoic acid macro test tubes
Sodium sulfate,Na2SO4 test tube rack
Barium Choride, BaCl2 evaporating dish
Sodium chloride, NaCl 5 mL pipet
filter paper 50 mL beaker
Activated charcoal hot plate
short stem funnel stirring rod
spatula test tube holder
test tube brush aspirator
250-mL beaker cotton
Masking tape 25-mL graduated cylinder

Procedure
1. Solution and Filtration
a. Mix thoroughly 0.5 gram of naphthalene and 0.5 grams of brown sugar in an
evaporating dish. Divide into two equal portions.
b. Transfer one portion into a test tube and add 3-5 mL water. Shake well and filter.
Which substance dissolved in water, sugar or naphthalene?
c. Place the other portion in another test tube and add 2 mL ethyl alcohol. Shake
well and filter. Which solute is dissolved in alcohol? What substance is left on the
filter paper?

2. Crystallization

a. Mix in a beaker 2 grams of impure urea (or benzoic acid) and 10 mL water in a
small beaker.
b. Boil the mixture gently for 5 minutes replacing occasionally the water lost by
evaporation. ( Perform this in fume hood)
c. Filter the solution while hot into a test tube immersed in ice water. Observe the
formation of crystals. Compare the crystals with the original sample.

3. Decolorization

a. Dissolve I gram of brown sugar into 10 mL water in a small beaker.

b. Divide the solution into two equal parts ( into two test tubes).
c. To one test tube, add ½ spatula of bone black or activated charcoal and boil for 5
min. (replace the water lost by evaporation).
d. Allow the hot mixture to cool and filter. Observe the color of the filtrate. Compare it
with that of the original sugar solution.

4. Sublimation ( Perform this procedure in the fumehood.)

a. Place 0.5 gram of benzoic acid and 0.5 grams of sodium sulfate in a dry
evaporating dish.
b. Cover the dish with a filter paper and tuck the edges tightly against the dish with
an adhesive.
c. Place pinholes in the center of the filter paper and cover this holed area with a
funnel. Be sure that sublimate will not leak once the mixture is heated.
d. Plug the top of the stem of the funnel with some cotton. Heat the dish slowly with
a low flame.
e. Once crystals accumulate inside the funnel, turn off the source of heat. Cool the
setup thoroughly.
f. Collect the sublimate that deposits on the walls of the funnel.
g. Dissolve a small amount of sublimate in barium chloride solution. What is the
composition of the sublimate, benzoic acid or sodium sulfate.

5. Distillation (Modified)
 a. Put 50 mL of 70 % rubbing alcohol in a 250 mL Florence flask. With a one- holed
cork insert a bent glass tubing into the cork. Fit this tightly into a Florence flask.
b. Insert the end of a glass tubing into another cork. Fit the cork into a 250 mL
Erlenmeyer flask as receiver.
c. Heat the mixture slowly until distillates are collected into the receiver. Test the
fluid inside the receiver by igniting the stirring rod which has been dipped into the
distillate. What is the distillate?

Result and Discussion

1. Mixture : naphthalene, brown sugar and water/ alcohol

1.1 Which substance dissolved in water, sugar naphthalene?_________________

1.2 Why? _________________________________________________________
1.3 Which substance dissolved in alcohol, sugar or naphthalene? _____________
1.4 What substance is left on filter paper? _______________________________
1.5 Why? _________________________________________________________
1.6 Define : solution ________________________________________________
filtration ________________________________________________
filtrate _________________________________________________

2. Mixture : Benzoic acid and water

2.1 In procedure 2.b, what is the purpose of boiling the mixture?_______________

_______________________________________________________________
2.2 In procedure 2.c, why should a solution be filtered while hot? ______________
_______________________________________________________________
2.3 Compare the crystals formed in the filtrate with that of the original sample.
_______________________________________________________________
2.4 Define crystallization ______________________________________________
_______________________________________________________________

3. Mixture of brown sugar and water

3.1 What is the function of bone black or activated charcoal? ________________

_______________________________________________________________
3.2 Compare the color of the filtrate with that of the original solution. __________
_______________________________________________________________
3.3 Define decolorization. _____________________________________________
_______________________________________________________________

4. Mixture of benzoic acid and sodium sulfate

 4.1 What is the purpose of plugging the tip of the stem of a funnel with cotton?
________________________________________________________________
4.2 Define sublimate.__________________________________________________
________________________________________________________________
4.3 Describe the sublimate. ____________________________________________
________________________________________________________________
4.4 What is the composition of sublimate, benzoic acid or sodium sulfate?________
________________________________________________________________
4.5 Define sublimation. ________________________________________________
________________________________________________________________

5. Mixture, 70 % rubbing alcohol

5.1 What is the fluid called inside the receiver?______________________________

5.2 How do you know? ________________________________________________
5.3 Define distillate.____________________________________________________
5.4 Define distillation. __________________________________________________
________________________________________________________________

Conclusion
Name ______________________ Date Performed______________
Course & Year _______________ Score _____________________

Laboratory Exercise No. 3

Paper Chromatography

Introduction

Most organic compounds obtained from natural sources and synthesized in laboratories are not
pure. Various methods are used for the purification of organic compounds that are based on the
nature of the compound and the impurity present in it. Among the various separation
techniques, chromatography is one of the most important separation technique extensively used
to separate mixtures into their components and the purification of the compounds.

The word chromatography was originated from two Greek words 'chroma' meaning 'colour' and
'graphine' meaning 'to write'. Chromatography means colour writing and it was first employed by
a Russian scientist Mikhail Tsvet. This method was first used for the separation of coloured
substances in plants.

In the chromatographic technique, the mixture of substances is applied onto a phase called the
stationary phase. The stationary phase may be solid or liquid. A moving phase that can be a
pure solvent or a mixture of solvents, or a gas is allowed to move slowly over the stationary
phase. This moving phase is called the mobile phase. When the mobile phase is moved over
the mixture on the stationary phase, the components of the mixture gradually separates from
one another.

In paper chromatography, the stationary phase is a special quality paper called chromatography
paper. Mobile phase is a solvent or a mixture of solvents. A solution of the mixture is spotted on
a line about 2 cm above from the bottom of the paper, called original line or base line and then
suspended in a chromatography chamber containing suitable solvent. The solvent rises up the
paper by capillary action and flows over the spot. The paper selectively retains different
components according to their differing partition in the two phases. The paper strip so
developed is called Chromatogram. The spots of the separated coloured compounds are visible
at different heights from the position of initial spot on the chromatogram. The spots of the
separated colourless components may be observed either under ultraviolet light or by the use of
an appropriate spray reagent. The distance travelled by the solvent from the original line is
called solvent front. The relative adsorption of each component of the mixture is expressed in
terms of its Retardation factor (Rf) (Retention factor).

Objectives
 1. Separate the coloured components present in the mixture of red and blue inks by
ascending paper chromatography.
2. Compute the Rf values of red and blue inks.
3. Separate the coloured components present in the extract of spinach leaves by
ascending paper chromatography.
4. Compute the Rf values of the components of extract of spinach leaves.

Materials

Jar with lid (chromatographic chamber) stirring rod

Mortar & pestle spatula (ceramic)
Pencil graduated cylinder
Whatman Filter Paper distilled water
Ruler red and blue ink
Capillary tube isopropyl alcohol
Pair of Scissors spinach leaves (fresh)
Watch glass

Procedure

I. Separation of Components from a Mixture of Red and Blue Inks

a. Take a Whatman filter paper strip and using a pencil draw a horizontal line 1 cm from
one end of the paper. Then draw another line lengthwise (vertically) from the centre of
the paper. Name the point at which the two lines intersect as P.
b. Using a fine capillary tube, put a drop of the mixture of red and blue inks at the point P.
Let it dry in air.
c. Put another drop on the same spot and dry again, so that the spot is rich in the mixture.
d. Pour equal amounts of isopropyl alcohol and distilled water into a chromatographic
chamber and mix it well using a glass rod. This is used as the solvent.
e. Suspend the filter paper vertically in the chromatographic chamber containing the
solvent in such a way that the pencil line remains about 2cm above the solvent level.
f. Close the jar with its lid and keep it undisturbed.
g. Notice the rising solvent along with the red and blue inks. After the solvent has risen
about 15 cm you will notice two different spots of blue and red colour on the filter paper.
h. Take the filter paper out of the jar and using a pencil mark the distance that the solvent
has risen on the paper. This is called the solvent front.
i. Dry the filter paper and put pencil marks at the centre of the red and blue ink spots.
j. Measure the distance of the two spots from the original line and the distance of the
solvent from the original line.
k. Calculate the Rf values of the red and blue inks.

2. Separation of Pigments from the Extract of Spinach Leaves

a. Take a few freshly plucked green spinach leaves.

b. Using scissors, cut the spinach leaves into small pieces and let them fall into the mortar.
c. Take a measuring cylinder that contains 5ml of isopropyl alcohol and pour it into the
mortar.
d. Grind the spinach leaves using the mortar and pestle.
e. Place the extract into a watch glass using a spatula.
 f. Take a Whatman filter paper strip and using a pencil draw a horizontal line 2 cm from
one end of the paper. Then draw another line lengthwise (vertically) from the centre of
the paper. Name the point at which the two lines intersect as P.
g. Using a fine capillary tube, put a drop of the extract of spinach leaves at the point P. Let
it dry in air. 
h. Put another drop on the same spot and dry again, so that the spot is rich in the leaf
extract.
i. Pour equal amounts of isopropyl alcohol and distilled water into a chromatographic
chamber and mix it well using a glass rod. This is used as the solvent.
j. Suspend the filter paper vertically in the chromatographic chamber containing the
solvent in such a way that the pencil line remains about 2cm above the solvent level.
k. Close the jar with its lid and keep it undisturbed.
l. Notice the rising solvent along with the coloured components of the leaf extract.
m. After the solvent has risen to about 15 cm you will notice two different spots of coloured
components on the filter paper.
n. Take the filter paper out of the jar and using a pencil mark the distance that the solvent
has risen on the paper. This is called the solvent front.
o. Dry the filter paper and put pencil marks at the centre of each spot.
p. Measure the distance of each spot from the original line and the distance of the solvent
front from the original line.
q. Calculate the Rf values of different components of leaf extract.

Result and Discussion

Table 3.1 Distance travelled by the component of ink and the solvent.

Distance travelled by the

SI Distance travelled by the solvent
Components component from the original Rf value
No. from the original line (cm)
line (cm)

1. Red      

2. Blue      

Inference
Rf value of red ink = ……………
Rf value of blue ink = …………..

Table 3.2 Distance travelled by the component of spinach leaves and the solvent.
SI.N Component Distance travelled by the Distance travelled by Rf
o component from the the solvent from the value
original line (cm) original line (cm)
1.  Orange  
(Carotene)
 2.  Yellow      
(Xanthophyll)
3. Light green      
(Chlorophyll a)
 4. Dark green      
(Xanthophyll)
Inference
Rf value of orange (Carotene) = ……………
Rf value of Yellow (Xanthophyll) = …………..
Rf value of Light green (Chlorophyll a) = …………..
Rf value of Dark green (Xhlorophyll b) = …………..

Conclusion
Name ______________________ Date Performed______________
Course & Year _______________ Score _____________________

Laboratory Exercise No.4

Boiling Point Determination

Introduction

The boiling point of a liquid is the temperature at which that liquid is converted to a gaseous
state. Boiling point is formally defined as the temperature at which the vapour pressure of the
liquid becomes equal to the pressure at the surface of the liquid. The boiling point of a liquid can
change if the pressure at the liquid's surface changes. Since pure substances have distinct
boiling point, boiling points are sometimes used to determine the purity of a substance.

Boiling points and melting points are recorded in the Handbook of Chemistry and Physics, and
can be found in the sections titled "Physical Constants of Organic Compounds" and "Physical
Constants of Inorganic Compounds".

In this experiment we will examine additional physical properties of organic liquids. One of the
two more important physical properties of pure substances is the boiling point.

Objectives

1. Determine the boiling point of an organic liquid.

2. Draw and label the set up for boiling point determination.

Materials

matches
small rubber bands
thermometer (100-1500C)
250 mL beaker
capillary tube
10-12 mm diameter test tube
heating set –up/ hot plate
spatula
5mL pipet
stirring rod
isopropyl (Rubbing) Alcohol)

Procedure
1. Make a test tube assembly by using the following directions:
a. Place about 1 mL of Isopropyl alcohol in a 10-12 mm diameter test tube.
 b. Using a small rubber band, attach a thermometer to the outside of the
test tube. The thermometer bulb should be even with the test tube's bottom.

c. Close one end of a capillary tube by heating the open end in an alcohol lamp. Be
certain that the end is close.
d. Insert the capillary tube into the test tube (open end facing down).

2. Make a water bath assembly by using the following directions.

a. Half fill a 100 mL or larger beaker with warm tap water. [Note: a water bath is used. If
the boiling point of the material is expected to be less than the boiling point of water;
otherwise, an oil bath is needed.]

b. Place the above test tube assembly in the water bath so that the surface level of the
alcohol in the test tube is beneath the surface level of the water in the water bath.

c. Place the beaker on the hotplate and, stirring frequently to ensure even heating.
Carefully heat the water bath with your heat source until the water bath boils and a
rapid stream of bubbles continuously emerges from the capillary tube. [Note: if an oil
bath is used, the oil does not boil; the stream of bubbles from the capillary tube is the
sole indicator that the liquid in the pipet or test tube is boiling.]

d. Remove the heat source and begin observing the stream of bubbles.

e. When the last bubble emerges from the capillary tube, record the temperature.

3. Reheat the water bath and repeat the cooling process two more times. Record the
temperature reading after each trial, and determine the average all three trials.

4. The published boiling point of isopropyl alcohol is 82.4 oC. Calculate the error between
the observed boiling point and the published value of the boiling point.

% error = (Difference in Published Boiling Point and Observed Boiling Point)/Published

Boiling Point X 100

Result and Discussion

Table 4.1 Boiling point determination

Substance Published Observed Boiling Point Average % Error

Boiling Point
Trial 1 Trial 2 Trial 3

Isopropyl
alcohol
 Questions:

1. How do you compare the observed boiling point and published boiling point?

2. What factors might have contributed to the difference in boiling point?

3. When is the oil bath used in experiments like this?

4. Draw and label the set up of the boiling point determination.

Conclusion
Name ______________________ Date Performed______________
Course & Year _______________ Score _____________________

Laboratory Exercise No.5

Melting Point Determination

Introduction

The melting point is the temperature at which a solid is converted to liquid. This is an important
property of solids. The melting point of solids, like the boiling point of liquids, is often used for
the identification of substances.

Boiling points and melting points are recorded in the Handbook of Chemistry and Physics, and
can be found in the sections titled "Physical Constants of Organic Compounds" and "Physical
Constants of Inorganic Compounds".

In this experiment we will examine additional physical properties of organic solids. One of the
two more important physical properties of pure substances is the melting point.

Objectives

1. Determine the melting point of an organic solid.

2. Draw and label the set up for melting point determination.

Materials

matches
small rubber bands
thermometer (100-1500C)
250 mL beaker
capillary tubes (melting point tubes)
heating set –up/ hot plate
spatula
stirring rod
mortar & pestle
powdered urea

Procedure
1. Seal one open end of capillary tube by heating it an alcohol lamp.

2. Push the open end of a capillary tube into the powdered urea.

3. Move the powder to the closed end of the capillary tube by tapping it on the table.
Repeat until the powdered urea occupies 1-2 mm of the capillary tube end.
 4. With rubber bands, attach the capillary tube to a thermometer and align the bulb of the
thermometer with the closed end of the capillary tube.

5. Make a water bath as before by half filling a 100 mL beaker with vegetable oil or
glycerol.

6. Place the thermometer/capillary tube assembly in the oil bath so that the surface level of
the powdered urea is beneath the surface level of the oil bath.

7. Place the beaker on the hot plate and stir frequently to insure even heating, carefully
heat the water bath with your heat source.

8. Note the temperature at which the urea melts. Remove heat source.

9. Let the urea cool and recrystallize. Repeat the procedure two more times and
determine the average of the results.

10. The published melting of urea is 132 oC. Compare your experimental (observed) result
with the accepted (published) value.

11. Calculate the percent error.

12. Dispose of the used capillary tubes by putting them in your trash can.

13. Draw the set-up for melting point and label it.

Result and Discussion

Table 5.1 Melting point determination

Substance Published Observed Melting Point Average % Error

Melting Point
Trial 1 Trial 2 Trial 3

Urea

Questions:

1. How do you compare the observed melting point and published melting point?
 2. What factors might have contributed to the difference in melting point?

3. Draw the set-up of melting point determination ( Label parts.)

Conclusion