Experiment No.

2
Part A. ALCOHOLS

Name: Christine Ken Mae N. Marcellana Date Performed: Sept. 7, 2021

Section: CHEM 17 – M (LAB) Date Submitted: Sept 9, 2021

IV. Data and Observations

Table 1. Reaction with Na metal
SAMPLE OBSERVATION
The sodium metal reacted steadily and entirely dissolved, releasing bubbles
Ethyl alcohol
(hydrogen gas), but the solution is now a dark brown hue due to the reaction.
The metal held its shape, but the white metal material melted and settled at
Isopropyl alcohol
the bottom of the test tube.
Halfway through the process, the sodium metal was dissolved and decolorized.
t-Butyl alcohol
The color of the alcohol is still completely transparent.
Write chemical equations below:

A. Ethyl Alcohol

CH3 − CH2 − OH + Na → CH3 −CH2 − O − Na + H2

B. Isopropyl alcohol

CH3− CH − CH3 + Na → CH3 − CH − CH3 + H2

l l
OH O − Na

C. t-Butyl alcohol

CH3 CH3
I I
CH3 − C − OH + Na → CH3 − C − O + Na + H2
I I
CH3 CH3

Table 2a. Oxidation with chromic acid (K2Cr2O7 in H2SO4)

Description of the reagent: Orange liquid (K2Cr2O7) and transparent liquid (H2SO4)

SAMPLE OBSERVATION
The hue of the orange liquid changed to a dark shade (almost entirely black)
Ethyl alcohol
The color of the orange liquid became darker, yet still lighter, than the color of
Isopropyl alcohol
ethyl alcohol, which is a translucent greenish-blue liquid.
The color of the orange liquid stayed constant.
t-Butyl alcohol
Chemical equations:

(LEGEND: → = H2SO4)

A. Ethyl Alcohol
CH3 − CH2 − OH + K2Cr2O7 → CH3COOH = H2O
[Cr2O72- → Cr3+]
B. Isopropyl alcohol
O
II
CH3 − OH CH3 + K2Cr2O7 → CH3 − C − CH3
I
OH

C. t-Butyl alcohol

CH3
I
CH3 − C − OH + K2Cr7O7 → NR
I
CH3

Table 2b. Oxidation with Potassium permanganate.

Description of reagent: Dark Purple in Color

SAMPLE OBSERVATION
After being mixed with the reagent, the sample took on a darkish pink hue
Ethyl alcohol
after being exposed to it.
The hue of the sample changed to brown after it was mixed with the reagent.
Isopropyl alcohol
After being mixed with the reagent, the sample took on a darkish purple hue
t-Butyl alcohol
after being exposed to it.
Chemical equations:

A. Ethyl alcohol
CH3 − CH2 − OH + KMnO4 → CH3 − COOH + O = Mn = O (s)

B. Isopropyl alcohol
CH3− CH − CH3 + KMnO4 → 2CH3 − CH − CH3 = O = Mn = O (s)
II
O
C. t-Butyl alcohol
CH3
I
CH3 − C − OH + KMnO4 → NR
I
CH3

Table 3. Lucas Test (Formation of Alkyl Halides)

SAMPLE OBSERVATION
The sample looked to be colorless and transparent on the visual inspection.
Ethyl alcohol
It looked that the sample was slightly cloudier than the Ethyl alcohol sample.
Isopropyl alcohol
This sample appears to be the cloudiest of the three samples tested thus far.
t-Butyl alcohol
Chemical equations:

A. Ethyl alcohol
CH3 − CH2 − OH + HCl → CH3= − CH2 − Cl + H2O
B. Isopropyl alcohol
CH3 − CH − CH3 + HCl → CH3 − CH − CH3 + H2O
I I
OH Cl

C. t-Butyl alcohol
CH3 CH3
I I
CH3 − C − OH + HCl → CH3 − C − Cl + H2O
I I
CH3 CH3

Table 4. Iodoform Test

SAMPLE OBSERVATION
Following the addition of the NaOH, the sample (which had been combined
Ethyl alcohol
with iodine) became clear and colorless.
Following the addition of the NaOH, the sample (which had been combined
Isopropyl alcohol
with iodine) became white and hazy.
Following the addition of the NaOH, the sample (when mixed with iodine)
t-Butyl alcohol
became clear, with a faint tinge of yellow showing through.
Chemical equations:

Table 5. Combustion
SAMPLE OBSERVATIONS(flame, color, sootiness)
The flame produced by this sample was significantly stronger than the flame
95% ethanol produced by the 45 percent ethanol sample. A blue flame was visible in the room. The
sample did not contain any soot.
When combusted, the flame was feeble. A blue flame was seen, and the sample did
45% ethanol
not appear to be tarnished by soot.

Table 6. Test for Methanol

SAMPLE OBSERVATIONS
Between the two layers, the hue of the junction transitioned from colorless to a pale
methanol brownish brown. The sample contained blackish hues at the bottom of the tube and
the color brown at the bottom of the tube.
Table 7. Solubility in Water
SAMPLE OBSERVATION
The material was easily soluble in water when examined under a microscope.
Ethyl alcohol
The sample was miscible in water, indicating that it was soluble.
Isopropyl alcohol
In addition to being miscible in water, the sample is also a floating in water.
t-Butyl alcohol

Table 8. Contraction in Volume

volume of water: 25 mL

volume of ethanol used: 25 mL

expected total volume of solution: 50 mL

actual volume of solution: 49.9 mL

V. Questions

1. Explain in the differences in the rates of reaction of the three types of alcohols with Na metal

The decrease in acidity of the alcohols is responsible for the differences in the rates of interaction
of the three types of alcohols with Na metal. Increasing electron density of the oxygen atom of the more
strongly substituted alcohol, as well as steric hindrance, are the primary causes of the decrease in acidity
and/or protons removed from the solution.

2. Based on the results of the oxidation tests, classify the alcohols tested according to the following
categories. (easily oxidizable, oxidizable, resistant to oxidation)

1. Primary alcohols – easily oxidizable

2. Secondary alcohols – oxidizable
3. Tertiary alcohols – resistant to oxidation

3. Suggest a simple chemical test that will differentiate between the following pairs. Specify the reagents
and the expected results.

a) a 1o alcohol and a 3o alcohol

The Jones test employs chromium trioxide in the presence of sulfuric acid to act as a
potent oxidizing agent, and the results are published in the journal Science. Jones'
reagent causes the conversion of a primary alcohol into an aldehyde, which is then
transformed into a carboxylic acid in the presence of the reagent. The chromium's
oxidation state is the most important factor in this test. In Jones' reagent, chromium is in
the +6 oxidation state, indicating that it is very reactive. This intense reddish-orange
color is due to the Cr(VI) complexes that are present in the solution. Because tertiary
alcohols do not react with chromium, no precipitate is formed, allowing the solution to
remain orange in color. So the Jones test can assist in distinguishing primary from
tertiary alcohols in a variety of circumstances.

b) a 2o alcohol and a 3o alcohol

 As a reagent, the Lucas test employs zinc(II) chloride in the presence of hydrochloric acid
as a method of detection. When used in the presence of an alcohol, the Lucas reagent
will halogenate the alcohol, resulting in a product that is insoluble in aqueous solutions.
The development of a carbocation as a result of the loss of the hydroxyl as water has a
significant effect on the rate at which this reaction occurs. When the Lucas reagent is
added to a tertiary alcohol, it will generate a stable carbocation, which will result in a
fast reaction. A second phase is formed in the reaction mixture as a result of the
intractable nature of the final halogenated product in water as a result of this.
Secondary alcohols will generate a carbocation that is less stable than tertiary alcohols,
but the reaction will take place at room temperature in a matter of minutes rather than
hours. Thus, the Lucas Test can assist in distinguishing between secondary and tertiary
alcohols.

c) t-butyl alcohol and s-butyl alcohol

A solution of chromium trioxide (CrO3) in sulfuric acid is known as the Jones reagent
(H2SO4). In addition to being a powerful oxidizing agent, it also has the ability to rapidly
oxidize primary alcohols and aldehydes to carboxylic acids, as well as secondary alcohols
to ketones. Alcohols react with the yellow-orange Jones reagent, which contains a Cr (VI)
atom and is yellow-orange in color. The Cr is reduced to Cr during the organic oxidation
process (III). The first two steps of the reaction mechanism provide an explanation for
why tertiary alcohols do not undergo oxidation when the Jones reagent is used to
perform the reaction. Because tertiary alcohols do not have a hydrogen atom linked to
this carbon, the reaction was unable to proceed past this stage in the reaction chain.
Because sbutyl is a secondary alcohol and t-butyl is a tertiary alcohol in this scenario,
Jones Oxidation may be used to distinguish between the two alcohols.

4. What are the compositions of 95% ethanol and 45% ethanol?

The following are the components of both the 95 percent and 45 percent ethanol:
• Ethyl alcohol
• Methyl Isobutyl Ketone
• Methyl alcohol
• Ethyl acetate
• Water

5. Account for the volume contraction when alcohol and water were mixed.

49.9 mL

6. Explain why smaller alcohols are soluble in water. Would alcohols having longer alkyl groups be
completely soluble in water?

Water dissolves smaller alcohol molecules more readily than larger alcohol molecules because
the hydroxyl groups in alcohol can easily create h-bonds with water molecules. Increases in the
length of the hydrocarbon would result in a decrease in the solubility of the alcohol.