ALCOHOLS

Experiment 1

Mahmoud Mohamed
ID - 128697
Abstract

The aim of this experiment is determining 4 samples of alcohols by different tests a

primary, secondary or tertiary alcohol should also be considered to determine the
alcohols. The acidity test, which acts as a detection function group in which alcohols
reacts with Na (sodium metal) to produce alkoxides and hydrogen gas. It is done by
taking 5ml of Alcohol and adding a piece of Na metal and observing a popping sound
occurring which is the evolving hydrogen gas. Solubility test is to see if alcohols are
miscible or miscible by using water to dissolve alcohol .The oxidation test is done to
differentiate Alcohols and aldehydes. Primary alcohols when oxidized gives aldehydes
and further oxidation produces carboxylic acid. Secondary alcohols oxidizes to form
ketones. The procedure is done by adding oxidizing agent K2 Cr2 O7 or KMnO4 to the
alcohol warming the mixture then adding 2 drops of sulfuric acid in the mixture in case of
adding K2 Cr2 O7. The result when adding potassium dichromate changes its color from
orange to green Cr+6 to Cr+3while adding potassium permanganate the violet color
disappears Mn+7 changes to Mn+2. Iodoform test which differentiate between ethanol and
methanol. Its procedure is adding I2 pellets (iodine) brown color appears and adding
NaOH to the mixture till yellow color. Ethanol is detected when it gives +ve result and
methanol when –ve result. Esterification test is done to ethanol and methanol to give the
ester. The procedures are 2ml of alcohol and same amount of organic acid with few drops
of H2SO4 heat the Mixture for 10 min and odor are observed. Ethanol and Ethanoic acid
produces ester and water which gives the fruity smell and methanol + salicylic acid gives
vix odor. Borax test for glycerol. 5ml of borax is added to glycerol and adding
phenolphthalein gives pinkcolor and adding dilute glycerol disappears the pink color.
Adding concentration of H2SO4 to Iso amyl which gives the reddish brown color.

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Table of Contents
Abstract ......................................................................................................................................................... 1
Introduction .................................................................................................................................................. 3
Results ........................................................................................................................................................... 6
Discussion.................................................................................................................................................... 13
References .................................................................................................................................................. 15

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Introduction

Oxidation test is done on primary, secondary and tertiary alcohols. During test an
Oxidizing agent is used which is the potassium dichromate with sulphuric acid. If the
oxidation occurs the orange color which contains dichromate ions is reduced to green
color containing chromium ions. In the case of primary alcohols it can be oxidized to
aldehydes or carboxylic acid. If the alcohol is oxidized to an aldehydes then its further
oxidized to carboxylic acid. In a secondary alcohol it can be oxidized to form ketones.
In a tertiary alcohol it can’t be oxidized by potassium dichromate so no reaction forms.
Tertiary alcohols doesn’t have free hydrogen atom so it can’t be oxidized. (Clark, 2003)
During the experiment Ethanol and methanol are primary alcohols and when adding
Oxidizing agent potassium dichromate K2Cr2O7 changes their color from orange to green
Cr+6 to Cr+3 and when oxidized produces aldehydes and further oxidation with water
gives carboxylic acid while tertiary alcohol, Isoamyl alcohol aren’t oxidized because it
lacks a free hydrogen atom which is a necessity in the oxidation process.
Acidity Test acts as a detection function group where the alcohol reacts with sodium
Metal Na to give the alkoxides and evolving hydrogen gas. Carboxylic acids heated with
Alcohols with an acid catalyst produces ester and water where sulphuric acid is used as a
catalyst. The esterification reaction is slow and is reversible an example is making ethyl
ethanoate from ethanoic acid and ethanol

(clark, 2003)

Esters are characterized as organic compounds and works when an organic compound

changes the hydrogen atom in the hydroxyl group in the organic acid. It is an reversible

reaction between alcohol and carboxylic acid (Clark, 2003).

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 Ester functional group

Alcohol + Carboxylic Acid Ester + Water

R'OH + RCOOH RCOOR' + H2O

During the experiment Ethanol + acetic acid gives us ethyl acetate (a fruity odor or green
apple) while methanol Methanol + salicylic acid produces methyl salicylate ( vix odor).
Iodoform test is done by using iodine and sodium hydroxide. The procedure is by
Adding iodine to the sample of alcohol with sodium hydroxide.
The sodium hydroxide acts to remove the color of iodine then the solution is warmed up
Till it produces the yellow color. If the pale yellow color appeared and precipitation
Occurs then it is a positive result for iodoform CHI3. (Clark, 2003) The test is done
On methanol and ethanol to differentiate between them. Ethanol will give the positive
Result while methanol gives the negative result. Its mechanism is

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Results
Alcohols
Unknown 1
Physical Characteristics:

Appearance: Colorless liquid

Color: Colorless

Solubility in water: Soluble in water

Chemical reactions:

Test Observation Result

Reaction with sodium metal
Oxidation with K2Cr2O7 test
Reaction with conc. H2SO4
Esterification
Borax Test
Iodoform test
Hydrogen gas evolved and a
poping sound is noticed
Color changed from orange
to green due to Cr+6 changes
to Cr+3
Not applicable
Produced a vix odor
Not applicable
Color changed when adding
iodine pellets and NaOH
Yellow color
It gives alkoxides with
Evolving hydrogen
gas
It is a primary alcohol
and are oxidized to
aldehydes and then
forms carboxylic acid
Not applicable
Methanol + salicylic
acid
Produces Methyl
salicylate
Not applicable
Negative result and
did not precipitated

Unknown is Methanol write the structure CH3OH

Comment using chemical equations

Methanol is a primary alcohol. Oxidation occurs due to the presence of free hydrogen

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atom so it is oxidized to aldehydes and further oxidation gives carboxylic acid.

When doing the iodoform test we found that the alcohol solution did not precipitated
which indicated the alcohol was methanol . The iodoform reaction happens a pale yellow
precipitate which is a positive result for iodoform.

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 Alcohols
Unknown 2
Physical Characteristics:

Appearance: liquid

Color: colorless

Solubility in water: soluble

Chemical reactions:

Test Observation Result

Reaction with sodium metal Hydrogen gas evolved and a
poping sound is noticed
Oxidation with K2Cr2O7 test Color changed from orange
to green due to Cr+6 changes
to Cr+3
Reaction with conc. H2SO4 Not applicable
Esterification Produced a fruity odor
(green apple)
Borax Test Not applicable
Iodoform test Color changed when adding
iodine pellets and NaOH
Yellow color
It gives alkoxides with
Evolving hydrogen
gas
It is a primary alcohol
and are oxidized to
aldehydes and then
forms carboxylic acid
Not applicable
Ethanol + Ehtanoic
acid produces ester +
water
Not applicable
Positive result and it
precipitated

Unknown is Ethanol write the structure CH3CH2OH

Comment using chemical equations

Ethanol is a primary alcohol. Oxidation occurs due to the presence of free hydrogen atom
so it is
oxidized to aldehydes and further oxidation gives carboxylic acid.

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When doing the iodoform test the alcohol solution turned pale yellow and precipitated
which is a positive result. Ethanol is the only primary alcohol to give the iodoform
reaction.

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 Alcohols
Unknown 3
Physical Characteristics:

Appearance: liquid

Color: colorless

Solubility in water: not soluble

Chemical reactions:

Test Observation Result

Reaction with sodium metal Hydrogen gas evolved
and a poping sound is
noticed
Oxidation with K2Cr2O7 test Color did not changed
It gives alkoxides with
Evolving hydrogen gas
It is a tertiary alcohol
which has no free
hydrogen atom so it
isn’t oxidized

Reaction with conc. H2SO4 When H2SO4 is added it It is an indicator for

chaned its color to reddish isoamyl alcohol
brown

Esterification Not applicable Not applicable

Borax Test Not applicable Not applicable

Iodoform test Not applicable Not applicable

Unknown is Isoamyl write the structure C5H12O

Comment using chemical equations

The first observation is the color did not change when oxidation occurs. It did not change
because it is a tertiary alcohol which doesn’t have a free hydrogen atom attach to it.The
second observation is the reaction with H2SO4 the color changed to reddish brown which
an indicator for Isoamyl alcohol.

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 Alcohols
Unknown 4
Physical Characteristics:

Appearance: colorless liquid “high viscosity”

Color: colorless

Solubility in water: soluble

Chemical reactions:

Test Observation Result

Reaction with sodium metal
Oxidation with K2Cr2O7 test
Reaction with conc. H2SO4
Hydrogen gas evolved It gives alkoxides with
and a poping sound is Evolving hydrogen gas
noticed
Color changed from It can be oxidized
orange to green due to
Cr+6 changes to Cr+3
Not applicable Not applicable

Esterification Not applicable Not applicable

Borax Test When adding borax and When adding glycerol to

phenol phetalin It changes to the solution the pink
pink color color vanishes an
indicator for glycerol
alcohol

Iodoform test Not applicable Not applicable

Unknown is Glycerol write the structure C3H8O3

Comment using chemical equations

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First observation it can be oxidized color changes from orange to green. The glycerol
alcohol has a high viscosity. The borax test led to the indentification of the alcohol when
adding borax with phenol phetalin the solution turns to pink color and when adding a
dilute glycerol vanishes the pink color.

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Discussion

1st Unknown
The first unknown was methanol. The first test was the solubility test and unknown sample was
miscible in water. The second test was the oxidation test the sample was oxidized to produce
aldehydes and carboxylic acid and the color changed from orange to green. It was known when
doing the iodoform test and the observation was that it did not precipitated and when doing the
esterification test it produced a vix odor.

2nd Unknown
The second unknown was ethanol. The sample was soluble in water. Ethanol is a primary
Alcohol so it did oxidized to aldehydes and then oxidized further to carboxylic acid. The
Iodoform test is done by adding iodine pellets to the alcohol and then adding sodium hydroxide
to remove the color of iodine. The solution did precipitated with pale yellow color which is a
positive result this shows that the alcohol sample is ethanol. The esterification test produced a
fruity odor.

3rd Unknown
The third known was isoamyl. During solubility test it did not dissolve in water. The oxidation
Test it did not oxidized which shows it is a tertiary alcohol and the color did not change stayed
Orange. When adding H2SO4 it reacts to give a reddish brown color which is an indicator for
Isoamyl alcohol.

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4th Unknown
The fourth unknown was glycerol. The solubility test results it did dissolve in water. It is
oxidized and the color changed form orange to green. The borax test showed that it is glycerol
when adding borax to the alcohol with phenol phetalin the color turns pink and then adding
dilute glycerol vanishes the pink color.

Questions

1- CH3OH negative result

CH3CH2OH positive result
CH3CH(OH)CH3 negative result
C6H5CH2OH negative result

2- When using K2Cr2O7 as an oxidizing agent the orange color is reduced to green color.
Cr+6 to Cr+3 while KMnO4 changes form Mn+7 to Mn+2.

3- Methanol and ethanol - iodoform test

Methanol and iso propanol oxidation test

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References
Clark, J. (2003). Esterification.

Http:// http://www.chemguide.co.uk/organicprops/alcohols/esterification.html

Clark, J. (2003). oxidation of alcohols.

Http:// http://www.chemguide.co.uk/organicprops/alcohols/oxidation.html

clark, J. (2003). THE TRIIODOMETHANE (IODOFORM) REACTION WITH ALCOHOLS.

Http:// http://www.chemguide.co.uk/organicprops/alcohols/iodoform.html

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