BSMLS 1-A

GROUP #4: LABORATORY REPORT

 Erika Jane Molvizar
 Angel Pico

 Jelica Hope Mencino

 Nithany Louise Pallon

EXPERIMENT 7
STEREOCHEMISTRY
EXPERIMENTAL PROCEDURES
A. CONFORMATIONS OF ETHANE
 Using the molecular model kit provided,
construct the molecule of ethane (CH3CH3)
 Rotate the molecule around C-C bond to show
the staggered and eclipsed conformers of
ethane.
 Draw the sawhorse and Newman projections of
these conformers in your worksheet.
EXPERIMENTAL PROCEDURES
B. CONFORMATIONS OF BUTANE
1. Using the molecular model kit provided,
construct the molecule of butane
(CH3CH2CH2CH3).
 Viewing along the C2-C3 bond, rotate the
molecule. When rotating, keep C2 in place, and
rotate C3 to the right or in clockwise direction.
Rotation is done every 60° and starts at dihedral
angle of 0 degree.
EXPERIMENTAL PROCEDURES
 Draw the Newman projection of the four
conformers that corresponds to the energy maxima
and minima in the energy diagram.
 Plot the energy diagram. Y-axis is energy; X-axis is
degrees of rotation along C2-C3. Label the points in
the energy diagram with the name of each
conformer.
2. Construct the model of 2-methylbutane. Do this by
removing one of the hydrogen in C2 of the butane
model you use in #1 and replace it with methyl (-CH3)
group.
EXPERIMENTAL PROCEDURES
 Viewing along the C2-C3 bond, rotate the molecule.
When rotating, keep C2 in place, and rotate C3 to
the right or in clockwise direction. Rotation is done
every 60° and starts at dihedral angle of 0 degree.
 Draw the Newman projection of the six conformers
that corresponds to the energy maxima and minima
in the energy diagram.
 Plot the energy diagram. Y-axis is energy; X-axis is
degrees of rotation along C2-C3. label the points in
the energy diagram with the letter to represent each
conformer.
EXPERIMENTAL PROCEDURES
C. CONFORMATIONS OF CYCLOHEXANE
1. Use the molecular model kit to build the chair
conformation of cyclohexane.
 In your worksheet, draw the Newman projection of
cyclohexane using the template provided. Also,
draw the chair conformation and label the axial (a)
and equatorial (e) hydrogens.
2. Using the model you built in #1, remove the
equatorial hydrogen from one carbon atom and the
axial hydrogen in the adjacent carbon. Replace these
with methyl (-CH3) groups to make 1,2-
dimethylcyclohexane.
EXPERIMENTAL PROCEDURES
 Using the template provided, draw the two
conformers of 1,2-dimethylcyclohexane.
3. Using the model you built in #1, remove the
equatorial hydrogens from two carbon atoms
adjacent with each other. Replace these with
methyl (-CH3) groups to make the stereoisomer of
1,2-dimethylcyclohexane formed in #2.
 Using the template provided, draw the two
conformers this(new) 1,2-dimethylcyclohexane.
EXPERIMENTAL PROCEDURES
4. Using the model you built in #1, remove the
equatorial hydrogen from one carbon atom and
the axial hydrogen from the third carbon away.
Replace these with methyl (-CH3) groups to make
1,3-dimethylcyclohexane.
 Using the template provided, draw the two
conformers.
EXPERIMENTAL PROCEDURES
5. Using the model you built in #1, remove the
equatorial hydrogen from one carbon atom and
the equatorial hydrogen from the third carbon
away. Replace these with methyl (-CH3) groups to
make the stereoisomer of 1,3-
dimethylcyclohexane formed in #4.
 Using the template provided, draw the two

conformers this (new) 1,3-dimethylcyclohexane.

RESULTS
A. CONFORMATIONS OF ETHANE

CONFORMATION SAWHORSE NEWMAN PROJECTION

REPRESENTATION

STAGGERED

ECLIPSED
RESULTS
Which Newman projection of ethane is more stable?
 Staggered
What causes the instability of the molecule?
 In the eclipsed conformation, the C-H bonds in the front
and back carbons are aligned with each other with
dihedral angles of 0 degrees, making it unstable. The
electron densities on the C-H bonds are closer together
than they are in staggered form. When two C-H bonds are
brought into a dihedral angle of zero degrees, the electron
clouds experience repulsion, which raises the energy of
the molecule.
RESULTS
B. CONFORMATIONS OF BUTANE
1. 3D model of butane is made (✓) ___Yes ___No

Newman Projection of the four conformers of Butane

RESULTS
Energy Diagram of the four conformers of Butane
RESULTS
2. 3D model of 2-Methylbutane is made(✓) ✓Yes ___No
Newman Projection of the conformers of 2-Methylbutane

Conformer A: (Dihedral Angle= 0) Conformer B: (Dihedral Angle= 60) Conformer C: (Dihedral Angle= 120)

Conformer D: (Dihedral Angle= 180) Conformer E: (Dihedral Angle= 240) Conformer F: (Dihedral Angle= 300)
RESULTS
Energy Diagram of the four conformers of 2-Methylbutane

Which conformers are of equal energy? Conformers B=D, and A=E

RESULTS
C. CONFORMATIONS OF CYCLOHEXANE
1. Chair conformation of Cyclohexane is made(✓) ✓Yes ___No
Newman Projection:

2. Conformers of 1,2-Dimenthylcyclohexane
RESULTS
Are the two conformers identical? Yes If not, circle
the one with lower energy.
Are the two methyl groupcis or trans with each
other? Cis
3. Conformers of the (new) 1,2-Dimethylcyclohexane
RESULTS
Are the two conformers identical? Yes if not, circle
the one with lower energy.
Are the two methyl groupcis or trans with each
other? Trans
EXPERIMENT 8
IDENTIFICATION OF
ORGANIC COMPOSITION
Part A: Nonchemical Tests
EXPERIMENTAL PROCEDURES

 Secure unknown samples from

Instructor

 Examined and determined the physical

state (melting point or boiling point),
color and odor
EXPERIMENTAL PROCEDURES

 Prepare a melting point apparatus set-up

 Prepare a melting point apparatus using
 150mL beaker or thiele tube if available
 A piece of stirring rod
 A thermometer where the capillary tube is
attached with the solid sample (about 1cm in
height)
 A clamp extension and holder where a cork is
attached to which a thermometer is inserted.
EXPERIMENTAL PROCEDURES
 A liquid bath (liquid petrolatum) is used to
provide the heat, which is placed in the beaker
 The whole thing is then placed on wire gauze
and heated to boiling
 Continually stir the bath to distribute the heat
evenly
 Determine the melting point of the unknown
sample
EXPERIMENTAL PROCEDURES
 Determine the boiling point of the liquid
unknown sample
 Place 2mL of the liquids in a clean dry test tube
 Suspend the thermometer in the tube so that the bulb is
about 1 inch above the surface of the liquid
EXPERIMENTAL PROCEDURES
 Heat the tube with a small, non-luminous flame until the
liquid gently boils. When the liquid boils, the cool sides
of the tube causes the vapor to condense and a ring
appears where the condensation stops
 When the temperature reading is constant, record the
boiling point of the liquid
 Record all results and calculate normal boiling point
RESULTS

Unknown Sample 1 Unknown Sample 2

PHYSICAL STATE SOLID LIQUID

MELTING/BOILING POINT 141-149°C 176°C

COLOR WHITE COLORLESS

ODOR ODORLESS Plastic Balloon-like smell

RESULTS
2a. Is Unknown Sample 1 pure or not? Explain

Unknown sample 1 is not pure because it

does not have constant/fixed melting point. It does
not melt completely at one temperature only.
RESULTS
2b. Is Unknown Sample 2 pure or not? Explain

Unknown Sample 2 is pure because it has

well-defined physical properties
RESULTS
2c. Would you be able to give the classification
of your unknown compound? Explain

Unknown Substance 2 is an Ethyl Acetate as

it has a boiling point of 176°C and has a plastic
balloon-like smell, which is actually ether-like and
fruity odor. Each compound is unique and has its
own properties that distinguish them from other
compounds.
RESULTS
3. If the melting points of the two substances are
the same, how can you determine if they are the
same without using any form of spectroscopy?
Explain.
RESULTS
 Solids
A pure solid has a constant/fixed melting point. i.e. it will
melt completely at one temperature only.
With impurities, the melting point of a substance is
affected in two ways:
1. The melting point is lowered. For example, pure ice
melts completely at zero degree Celsius but the ice we
make at home from tap water will start to melt before zero
degree Celsius. The more impurities a substance contains,
the lower its melting point will be.
2. Melting would occur over a range of temperatures
and not at a constant/fixed temperature.
RESULTS
4. An unknown compound gave a melting point
of 230°C. When the molten liquid solidified, the
melting point was predetermined and found to be
131°C. Give a possible explanation for this
discrepancy.
RESULTS
A pure organic solid has a definite and sharp
(sudden, rapid and complete) melting point, while
an impure substance has a lower and indefinite
melting point.
EXPERIMENT 9
IDENTIFICATION OF
ORGANIC COMPOUNDS
Part B: Solubility Characteristics
EXPERIMENTAL PROCEDURE
 Place 45mg (0.045g) sample in a test tube
 Add a total of 1.5mL of solvent added in three
portions from a graduated dropper. After
addition of each portion, the sample is stirred
vigorously with a glass stirring rod for 1.5 to 2
minutes. If the sample is water, soluble, test the
solution with litmus paper to assist in
classification according to the Solubility Scheme.
 Test with litmus paper, dip the end of the
stirring rod into the solution and then gently
touch the litmus paper in a watch glass with the
rod.
 In doing the solubility tests follow the Solubility
Scheme in the order given. Keep a record of your
observations.
STEP 1: Test for water solubility. If soluble test
with litmus paper
STEP 2: If water soluble, determine the solubility
in diethyl ether. This test further classifies water-
soluble material
STEP 3: Water-insoluble compounds are tested
with 5% aqueous NaOH solution
RESULTS

SOLUBILITY IN UNKNOWN SAMPLE 1 UNKNOWN SAMPLE 2

WATER Soluble in Water

DIETHYL ETHER Insoluble in Diethyl Ether

Unknown sample 1 is neutral in blue and red litmus paper

RESULTS
 Classification of unknown compounds

Unknown Sample 1: ETHYL ACETATE

Unknown Sample 2: SODIUM CARBONATE

QUESTIONS
 The following six substances have
approximately the same boiling point and all are
colorless liquid Suppose you were given six
unlabeled bottles, each of which contained one
of these compounds. Explain how you would use
simple chemical tests to identify the contents of
each bottle.
QUESTIONS
 ETHANOIC ACID
Step by Step Test:
1. Water soluble? YES
2. Litmus paper color? RED
3. Ether soluble? YES
QUESTIONS
 PROPYL BUTANOATE
Step by Step Test:
1. Water Soluble? NO
2. 5% NaOH Soluble? NO
3. Soluble in concentrated H2SO4? YES
4. HCl Soluble? NO
5. 85% H3PO4 soluble? YES
QUESTIONS
 1 – Butanol
Property : 4 carbon alcohol
Step by step:
Is it water soluble? Yes
Using neutral litmus paper, what clor will it yield?
Purple (neutral)
If red litmus? Red (no color change = neutral or acidic)
If blue litmus? Blue (no color change = neutral or basic
QUESTIONS
 TOLUENE
cyclohexane(aromatic) with methyl attached
(saturated carbon)
1. Insoluble in water
2. Insoluble in 5% NaOH
3. Insoluble in 5% HCl
4. Insoluble in Conc H2SO4
QUESTIONS
 DIISOBUTYLAMINE
clear colorless liquid with an ammonia-like odor.
Insoluble in water and less dense than water.
Hence floats on water.
Secondary Amine with 8 carbons
1. Insoluble in water
2. Insoluble in 5% NaOH
3. Soluble in 5% HCl
QUESTIONS
 STYRENE
Aromatic compound with unsaturated carbon
Insoluble in water and less dense than water.
Steps:
1. Insoluble in water
2. Insoluble in 5% NaOH
3. Insoluble in 5% HCl
4. Soluble in conc H2SO4
5. Insoluble in 85%H3PO4
QUESTIONS
 A colorless liquid, C4H6O, having a boiling point of
97-98°C was found to be soluble in water and also
in ether. It gave a negative test for the presence of
halogens, sulfur, and nitrogen. It did, however, give a
positive test for 2,4-dinitrophenylhydrazine reagent.
It gave a negative result when treated with ceric
nitrate solution and also Tollen’s reagent. Treatment
with ozone followed by hydrolysis in the presence of
zinc gave formaldehyde as one of the products.
What is the structure and the name of the colorless
liquid?
QUESTIONS
 Methyl vinyl ketone = ketone, has unsaturated /
double bonds and yields formaldehyde in
ozonolysis