LABORATORY REPORT

SEM 1 2015/2016

EBT 105: ORGANIC CHEMISTRY

EXPERIMENT 2:
IDENTIFICATION OF ALCOHOL

MARKS
GROUP 7
Objective /5
NAME MATRIC NO
Introduction /15
Materials & /5
1. SARAH AFIQAH BINTI MOHD 151171315 Equipments
ZAILANI Procedures /10
2. TAN MEI AI 151171320 Results /15
Discussion /30
3. NHURFITRI BINTI SAMSURI 151171292
Conclusion /10
References /5
4. LIM JIA LIANG 151171277
Appendix & /5
Format
5. MUHAMAD FIKRI BIN MAZLAN 151171286
TOTAL /100

LECTURER
MRS. SITI SALMI BINTI SAMSUDIN

MR. MOHAMAD SYAHMIE BIN MOHAMAD RASIDI

DR. MOHD KAHAR BIN ABDUL WAHAB

 1. OBJECTIVE

1.1 To determine the solubility of various alcohols and distinguish the primary,
secondary and tertiary alcohols.

2. INTRODUCTION

Specific group of atoms in an organic molecule can determine its physical and
chemical properties. This group are referred to as functional groups. Organic compound
that contain the functional group –OH, the hydroxyl group that called alcohols. Alcohols
have higher boiling point than expected when compared with other organic molecules
with similar relative molecular mass. The alcohol with lower molar mass, is liquid at
room temperature. This occur because of hydrogen bonding between alcohol molecules.
[1] (Roger Norris, 2011)
Alcohols are classified into three categories: primary (1º), secondary (2º) and
tertiary (3º). This classification is based on the number of carbon-containing groups (R-
for alkyl or an aromatic group) attached to the carbon bearing the hydroxyl group. If the
carbon bearing the –OH has one R- group, the molecule is primary alcohol. If two R-
groups are attached, it is a secondary alcohol. If three R- groups attached, the alcohol is
tertiary.
2.1 Physical Properties of Alcohols

The hydroxyl group present in all alcohols is a polar functional group. The
polarity of this group allows all alcohols to form hydrogen bonds. Small
chain

alcohols are able to mix with water because of the hydrogen bonding
interactions that will occur between the hydroxyl functional group and the
water. If the R- group of the alcohol becomes too large however, the
solubility of the alcohol will decrease.

2.2 Chemical Properties

The classification of an alcohol as primary, secondary or tertiary (see

above) affects the chemical properties of the alcohols. This difference in
chemical properties can be used as a mean of identification.
 3. CHEMICALS/APPARATUS:

3.1 Ethanol
3.2 1-butanol
3.3 2-butanol
3.4 2-methyl-2-propanol
3.5 Dichloromethane
3.6 Chromic acid solution
3.7 Acetone
3.8 Distilled water
3.9 Test tube
3.10 Dropper
3.11 Graduated cylinder

4. PROCEDURE

4.1 Solubility Test

4.1.1 10 drops of each alcohol (ethanol, 1-butanol, 2-butanol, 2-methyl-2-

propane) was placed into its own test tube. 1-2 ml of water was added to
each tube. The observation was recorded on the data sheet.

4.1.2 Another 10 drops of each of the above alcohols was placed into its own
test tube. 1-2 ml of dichloromethane was added. The observation was
recorded on the data sheet.

4.2 Identification of Organic Compounds

4.2.1 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 blue-green solution.
10 drops of acetone was placed in a test tube. 5 drops of ethanol and 2 drops of chromic
acid were added to the tube. The color of the solution was noted and recorded on the data
sheet. This procedure was repeated for 1-butanol, 2-butanol, and 2-methyl-2-propanol.
 5. RESULT

The observation in the Solubility test and Chromic Acid test and question 5.3 and
5.4 was reported and discussed.

5.1 Solubility test: The observation properties to the molecular structure.

Experiment Ethanol 1-Butanol 2-Butanol 2-methyl-2-

propanol
Solubility in H2O Completely soluble Insoluble Insoluble Completely soluble

Solubility in Completely soluble Completely soluble Completely soluble Completely soluble

CH2Cl2

The diagram of solubility in H2O of tested alcohol

1-Butanol
2-Butanol
1-
Ethanol 1. 2-methyl-2-propanol

2.

From the result, ethanol and 2-methyl-2-propanol can only completely soluble in
the water, while 1-butanol and 2-butanol are insoluble. This can be conclude that
shorter hydrocarbon portion chain of alcohol are soluble in water and solubility of
alcohols are depends on the molecular structure. [2] (William H. Brown M. K.,
2009)
 The diagram of solubility in CH2Cl2 of tested alcohol

1-Butanol
2-Butanol

Ethanol 2-
3.
2-methyl-2-propanol

4.

All alcohols in this experiment completely dissolve in CH2CI2, because alcohols are
organic solvent as well as polar solvent which can be dissolve in most organic solvent.
So, as the low portion of hydrocarbon chains, alcohols are able to soluble in polar
solvents. CH2Cl2 is an organic solvent, as a result that ethanol, 1-butanol, 2-butanol and 2-
methyl-2-propanol can completely dissolve due to the similar interaction with the concept
of “like-dissolve-like”. [3] (William H. Brown M. K., 2009)

5.2 Identification of organic compound (Chromic Acid Test): The observation

properties to the molecular structure.

Experiment Ethanol 1-butanol 2-Butanol 2-methyl-2-

propanol
Chromic acid Dark blue-green Blue-green Light blue-green No visible change,
(CH2Cl2) test solution solution solution remain red-orange
solution
The diagram of chromic acid test, CH2Cl2.

Ethanol 1-Butanol 2-Butanol 2-methyl-2-propanol

3- 5. 6.

Ethanol 1-Butanol

7.

2-Butanol 2-methyl-2-propanol

2. 1.
 6 DISCUSSION

6.1 Alcohols are more soluble than hydrocarbon in water, why?

Alcohols are completely soluble in water by forming hydrogen bonds
with water molecules while hydrocarbons are not able form hydrogen bonds
with water.[4] (Maitland Jones Jr, 2009) Because alcohol is an organic
molecule containing an -OH group which can occur a hydrogen bonding
when a lone pair of electron on an O to the hydrogen atom of the water. In
this case, any molecule which has a hydrogen atom attached directly to an
oxygen is capable of hydrogen bonding. Hydrocarbon is insoluble in water
that due to the reason of no O atom that can form hydrogen atom to the
water.

6.2 Structure of the alcohols and the formula of the oxidation product of

alcohols.

Ethanol

H H
H H H H OH
+ | |
| | H /Cr2O72- H+/Cr2O72- | | |
H - C - C =O
H - C - C -OH
| | → |
H
→ H - C - C - C =O
| |
H H H H

H+/Cr2O72- H+/Cr2O72-
Ethanol
→ Ethanal
→ Ethanoic acid

1-butanol

H H H H H H H H H H H OH
| | | | H+/Cr2O72- | | | | H+/Cr2O72- | | | |
H- C - C - C - C -OH
| | | | → H- C - C - C - C =O
| | | → H- C - C - C - C =O
| | |
H H H H H H H H H H

H+/Cr2O72- H+/Cr2O72-
1-butanol
→ Butanal
→ Butanoic acid
2-butanol

H H H H H H H
| | | | H+/Cr2O72- | | |
H- C - C - C - C -H
| | | | → H- C - C - C - C -H
| || | |
H OH H H H O H H

H+/Cr2O72-
2-butanol
→ 2-butanone

2-methyl-2-propanol

H
|
H H-C-H H
| | |
H- C - C - C -H
| | |
H OH H

2-methyl-2-propanol (No oxidation occur)

6.3 Why the rule of solubility of alcohols does depends upon their molecular
size?

The solubility of alcohols in water gradually decreases as the

hydrocarbon portion of the molecule lengthens. Long-chain alcohols are
more behavior likely to hydrocarbon, therefore, less like water. [5]
(JohnMcMurry, 2007).That is because hydrocarbon is hydrophobic,
hydrophobic is the non-polar part of alkyl group which is not attracted the
H2O caused the solubility. So, the longer the carbon chain, the decreases of
the solubility of alcohol soluble in the water. Therefore the solubility of
alcohols decreases due to the molecular size increases.
 7. REFERENCE
[5] JohnMcMurry. (2007). Organic Chemistry,7th edition. Physical Sciences : David Harris.

Maitland Jones Jr, S. F. (2009). Organic Chemistry. W.W.Norton & Company.

Roger Norris, L. R. (2011). Alcohol. United Kingdom: Cambridge International A Level .

William H. Brown, M. K. (2009). Introduction to Organic Chemistry and Biochemistry. Brookes

Cole.

William H. Brown, M. K. (2009). Organic Chemistry. Brooks Cole.

8. CONCLUSION

In this experiment, ethanol and 2-methyl-2-propanol are completely soluble

in water, but 1-butanol and 2-butanol are not soluble in water. Because alcohol is
an organic molecule containing an -OH group. Any molecule which has a
hydrogen atom attached directly to an oxygen is capable of hydrogen bonding.
Ethanol and 2-methyl-2-propanol are completely soluble in water by
forming hydrogen bonds with water molecules while hydrocarbons are not able
form hydrogen bonds with water. However, 1-butanol and 2-butanol are not
soluble in water due to the long hydrocarbon chain that caused hydrophobic to the
water, therefore 1-butanol and 2-butanol are insoluble in water.
Therefore lower alcohols are completely soluble in water by forming
hydrogen bonds with water molecules while hydrocarbons are not able form
hydrogen bonds with water. The solubility of alcohols in water gradually
decreases as the hydrocarbon portion of the molecule lengthens.
9. APPENDIX