Investigation 1.5.

1 Reactions of Four
Isomers of Butanol

Submitted By: Shane Rollit, Nicholas Casadiego,

Joey Bucci Penney
Submitted To: Mr. Romano
Submitted On: November 6, 2015
Course Code SCH 4UP - 02
Purpose:

To test the reactions of primary, secondary, and tertiary alcohols with acid and with an
oxidizing agent. (page 64 of textbook Nelson Chemistry 12)
Materials/Apparatus:
Refer to page 64 of textbook Nelson Chemistry 12
4 test tubes instead of 3 used.
In addition to the three isomers of butanol listed in the textbook, isobutanol was also tested.
Procedure/Method:

Refer to page 64 of textbook Nelson Chemistry 12

Students poured and handled hydrochloric acid and potassium permanganate solution
instead of teachers (Step 2).
In every instance of where alcohols were measured out or introduced to other
chemicals, a fourth test tube was used with 10 drops of isobutanol (Steps 2-7).

Observations
Part 1:
Test Tube # Butanol Used (2 drops)

Hydrochloric Acid

Observations

N-Butanol

10 drops

-Pale yellow
-Translucent

Isobutanol

10 drops

-Pale yellow
-Translucent

S-Butanol

10 drops

-Dark yellow
-Translucent

T-Butanol

10 drops

-Precipitate formed
-Cloudy yellow (a bit
opaque)

Part 2:
Test Tube # Butanol Used (4
drops)

Potassium
Permanganate
Solution

Observations

N-Butanol

20 drops

-Precipitate formed
-Dark red/purple (Opaque)

Isobutanol

20 drops

-Precipitate formed
-Dark purple (Opaque)

S-Butanol

20 drops

-Clear (Transparent)
-Bits of precipitate formed

T-Butanol

20 drops

-Light purple
-Translucent

Discussion
A.
During part one of the lab n-butanol turned a pale yellow and was completely
translucent from its basic clear colour . Isobutanol also turned a pale yellow and was

completely translucent also from its basic clear colour. S-butanol turned dark yellow and
translucent form its original clear colour. Finally t-butanol turned yellow and had a
precipitate form.
During part two of the lab n-butanol formed a precipitate as well as changed colour to
a dark reddish purple colour from its original purple colour. Isobutanol formed a
precipitate how ever they no colour change was occurred. S-butanol turned entirely clear
from its original purple colour and formed a precipitate. Finally t-butanol did not have
any changes that would note a reaction.
All of the changes listed above are evidence of a chemical reaction except for the tbutanol portion of the experiment in part two of the lab.

B.

Reactions With Hydrochloric Acid Solution

Oxidization Reactions in the Presence of Potassium Permanganate Solution

C. The evidence collected does allow the group to achieve the purpose. The purpose
is to test the reactions of primary, secondary and tertiary alcohols with acid and with an
oxidizing agent. Throughout the lab, visible changes in chemical properties are observed
within each individual experiment. Also, due to the variables used in this lab we were
able to see how the different types of alcohols reacted to being mixed with the
hydrochloric acid (acid) and the potassium permanganate solution (oxidizing agent),
therefore allowing the group to achieve the initial purpose to test the reactions of primary,
secondary, and tertiary alcohols with acid and with an oxidizing agent.
D.
When an alcohol undergoes a halogenation reaction a process similar to a
substitution reaction occurs. The hydroxyl group within the alcohol is separated from the
rest of the chain, and then bonds with the hydrogen atom of (in this case) the
hydrochloric acid, forming a water molecule. The halogen, here chlorine, then takes the
place that the hydroxyl group had within the original molecule. This general reaction
occurs with primary, secondary, and tertiary alcohols, however, the reaction occurs with
greater speed with tertiary alcohols, hence the greater effect that was observed. In
addition, a different isomer of chlorobutane was formed from each isomer of butanol.
Within oxidization, different products are created from different isomers of
alcohols. From the reaction of primary alcohols, such as n-butanol and isobutanol,
aldehydes are created along with water. Two butanols have the hydrogen from their

hydroxyl groups stripped by an oxygen from an O2 along with another hydrogen attached
to the primary carbon, creating two water molecules. This allows frees the primary
carbons to create double bonds with the oxygen from the hydroxyl groups, forming two
aldehydes. In the reaction with secondary alcohols, ketones are produced in a similar
manner as aldehydes are created with primary alcohols. The difference in this is that the
hydroxyl groups were located on a non-terminal carbon, and thus when creating a double
bond with oxygen, they are unable to have the hydrogen attached that creates an
aldehyde. Tertiary alcohols are unable to undergo oxidizing reactions, as they are unable
to create a double bond on an oxygen, as the tertiary carbon is already attached to three
other carbons.
E.
3-methoxy-1-butanol can is a very good solvent which makes it very useful for removing
paint from brushes, metals, and most other things that paint may need to be removed from. Yet it
leaves the item that the paint is on undamaged. 2-butanone is a also used as a solvent the in an
industrial setting. This is because it is able to weld plastics together.

Conclusion
In this lab the group observed and tested the resultant of what reaction would occur if primary,
secondary and tertiary alcohols were mixed with an acid and with an oxidizing agent. The
butanols used were N-Butanol, S-Butanol, Iso-Butanol and T-Butanol. Two drops of
hydrochloric acid were added to the four butanols used, and once the reaction was completed the
results were observed and recorded. (See Observation Tables - Part 1). 20 drops of potassium
permanganate solution were added to additional samples of the 4 butanols used. The results of
these reactions were also observed and recorded. (See Observation Tables - Part 2).
Through this procedure the increased rates of halogenation occurring in alcohols of
higher degrees were observed. These results were derived by the increased strength of opacity
and colour intensity observed following the reactions with s-butanol and particularly t-butanol.
The different oxidation reactions with differing isomers could also be derived from the results
obtained in the experiments. The reddish tint obtained following the oxidation of primary
alcohols differs their results with the clear solution following the results of s-butanol oxidizing,
as well as the solution of t-butanol, which remained the purple colour of the introduced
potassium permanganate solution.
Possible sources of error within this procedure include the random error of possible
airborne contaminants introduced to the test tubes. Additionally moisture may have existed
within the reaction environment pre-reaction. Human error exists in the imprecise measurements
of drops reacted, instead of a specified amount of reactants. This source of error could be
mitigated through the use of a specific volume of reactants instead of drops.