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Title

Reactions of alcohols

Objective
To investigate the reactions of alcohols with oxidizing agents and sodium.

Apparatus
250 mL beaker, thermometer, Bunsen burner, tripod stand, wire gauze,test tubes, test tube rack

Materials
Ethanol, butan-1-ol, butan-2-ol, 2-methylpropan-2-ol, Na2Cr2O7, H2SO4, KMnO4, sodium

Introduction
Alcohols are compounds in which one or more hydrogen atoms in an alkane have been
replaced by an OH group. The molecule of alcohol is polar since the OH group attracts
negative charge from whole carbon chain. They soluble in water and organic compounds.
Alcohols can react as acid and bases ,and so they have amphoteric properties.There are three
classes of alcohol, which are primary alcohols, secondary alcohols and tertiary alcohols. For
primary alcohols, the carbon carries the OH group is only attached to one alkyl group. For
secondary alcohols, the carbon with the OH group attached is joined directly to two alkyl
groups, which maybe the same or different. While for tertiary alcohols, the carbon atom holding
the OH group is attached directly to three alkyl groups, which maybe any combination of same
or different. As one moves from primary alcohol to secondary to tertiary alcohol with the same
backbone, the hydrogen bond strength, the boiling point and the acidity typically decrease.
Alcohol can be oxidized by using sodium or potassium dichromate(VI) solution or acidified
KMnO4. Primary alcohol can be oxidized to either aldehydes or carboxylic acid, while secondary
alcohol can be oxidised to ketones. Tertiary alcohol cannot be oxidised and thus no reaction.
Alcohol can also react with sodium to produce alkoxide salt and hydrogen gas.

In this experiment, ethanol and butan-1-ol is primary alcohol. Butan-2-ol is secondary


alcohol and 2-methylpropan-2-ol is tertiary alcohol. In this experiment, the oxidation of alcohols
is carried out by using chromate and dichromate ion in part A. In part B, it is reacted with
sodium.

Procedure
Part A: Reaction of alcohols with oxidizing agents
( Reaction with dichromate ion )
1) A hot water bath is prepared by heating 100 mL of tap water on a 250 mL beaker to 80
C. The Bunsen is turned off.
2) 2mL of ethanol, butan-1-ol, butan-2-ol and 2-methlypropan-2-ol are placed into four
separate labelled test tubes respectively.
3) In another test tube, 4 mL 0.1 mol L-1 Na2Cr2O7 and 2 mL of 6 mol L-1 H2SO4 is mixed.
4) 1 mL of the acidified Na2Cr2O7 is poured into each of the test tubes containing the
alcohols and heat them in the hot water bath for about 5 minutes. If the aqueous and
alcoholic phases do not mix, the mixture is shaked occasionally.
5) Any evidence of reaction is observed carefully and the relative rate of the reaction of
each alcohol. Where a reaction has taken place carefully smell the contents of the tube.
Write your observations in a suitable table.

( Reaction with permanganate ion )

1) 2mL of ethanol, butan-1-ol, butan-2-ol and 2-methlypropan-2-ol are placed into four
separate labelled test tubes respectively.
2) In another test tube, 2 mL of 0.1 mol L-1 KMnO4 and 1 mL of 6 mol L-1 H2SO4 is mixed.
3) 3-5 drops of the acidified KMnO4 is added to each of the test tubes containing the
alcohols and is shaked gently.
4) Any evidence of reaction is observed carefully and the relative rate of the reaction of
each alcohol is noted. Where a reaction has taken place , the contents of the tube are
smelled carefully. Write your observations in a suitable table.
Part B: Reaction of alcohols with sodium
1) 2mL of ethanol, butan-1-ol, butan-2-ol and 2-methlypropan-2-ol are placed into four
separate dry test tubes respectively.
2) Four small freshly cut pieces of sodium is obtained from your teacher.
3) One piece of sodium is added to each of the test tubes containing the alcohols. Any
evidence of reaction is observed carefully and the relative rate of reaction of each alcohol
is noted.

Results

Part A( Reaction with dichromate ion )

Alcohol

Observation

Ethanol

Solution changes from orange to green.

Butan-1-ol

Solution changes from orange to green.

Butan-2-ol

Solution changes from orange to green.

2-methylpropan-2-ol

Solution remain orange.

Part A ( Reaction with permanganate ion )


Alcohol

Observation

Ethanol

Solution changes from purple to colourless.

Butan-1-ol

Solution changes from purple to colourless.

Butan-2-ol

Solution changes from purple to colourless.

2-methylpropan-2-ol

Solution remain purple.

Part B ( Reaction of alcohols with sodium )


Alcohol

Observation

Ethanol

The reaction with sodium is the fastest. The


small piece of sodium is lost and bubble gas is

Butan-1-ol

released.
The reaction with sodium is the second fast.
The piece of sodium is lost and bubble gas is

Butan-2-ol

released.
The reaction with sodium is the third fast. The
small piece of sodium is still remain but bubble

2-methylpropan-2-ol

gas is released.
The reaction with sodium is the slowest. The
small piece of sodium still remain but bubble
gas is released.

Discussion
In this experiment, in part A, ethanol and butan-1-ol is primary alcohol, butan-2-ol is
secondary alcohol and 2-methylpropan-2-ol is tertiary alcohol. When ethanol, butan-1-ol and
butan-2-ol react with dichromate ion, the solution change from orange to green. This is because
oxidation of alcohols occurs, while dichromate ion undergo reduction. The orange solution
containing the dichromate(VI) ions is reduced to a green solution containing chromium(III)
ions.The primary alcohol is oxidised to aldehydes. While, when 2-methylpropan-2-ol is reacted
with dichromate ion, no colour changes occur. No reaction occurs because tertiary alcohol arent
oxidised by acidified dichromate ion.
When ethanol, butan-1-ol and butan-2-ol react with permanganate ion, the solution change
from purple to colourless. This is because oxidation of alcohols occurs, while permanganate ion
undergo reduction. The purple solution containing the permanganate ions is reduced to a
colourless solution. The primary alcohol is oxidised to aldehydes. While, when 2-methylpropan2-ol is reacted with dichromate ion, no colour changes occur. The solution still remain purple. No
reaction occurs because tertiary alcohol arent oxidised by acidified dichromate ion.
In part B, different alcohol is reacted with sodium. When all of the alcohol react with
sodium, bubble gas is released. The bubble gas released is hydrogen gas. This is because, when

alcohol react with metal, it will produce alkoxide salt and hydrogen gas. Regarding the reactivity
of different alcohol with sodium, the longer the carbon chain of alcohol, the less vigorous the
reaction between alcohol and sodium. Ethanol react the fastest with sodium. This is because
ethanol has the shortest carbon chain among the alcohols and also it is the most exposed as the
OH group attached on the most outside, which is on the first carbon.So, it has the most hydrogen
bonding and react the most with sodium. The second fast to react with sodium will be butan-1-ol
and it also has the OH group attached on the most outside, the first carbon, and has hydrogen
bonding. But, it has longer carbon compared to ethanol. Next, butan-2-ol is the third fast to react
with sodium. This is because butan-2-ol is surrounded by 2 alkyl group. So, it has less hydrogen
bonding compared to butan-1-ol and ethanol. The reaction is not that vigorous. Lastly, 2methylpropan-2-ol is the last to react with sodium. This is because it is not a straight chain. It is a
branch chain and also it is surrounded by 3 alkyl group. So, it has the least hydrogen bonding and
thus react the slowest.

Conclusion
When primary and secondary alcohol react with dichromate ion, oxidation of alcohol will occur
and change the solution from orange to green. When primary and secondary alcohol react with
permanganate ion, oxidation will occur and decolourise the solution. Both ions have no reaction
with tertiary alcohol. All alcohol can also react with sodium to produce alkoxide salt and
hydrogen gas.

Questions
1) Ethanol, butan-1-ol, butan-2-ol
2) Ethanol

Ethanal

Butan-1-ol

Butanal

Butan-2-ol

Butanone

2-methylpropan-2-ol = No reaction.

3) Oxidation of ethanol by Cr2O72

Oxidation of ethanol by MnO4

4) Reaction with Cr2O72


( Butan-1-ol)

( Butan-2-ol)

( 2-methylpropan-2-ol) = No reaction.

Reaction with MnO4


( Butan-1-ol)

( Butan-2-ol)

(2-methylpropan-2-ol) = No reaction.
5) Ethanol, butan-1-ol, butan-2-ol, 2-methylpropan-2-ol
6) 2 R-OH + 2 Na

2 R O- Na+ + H2

7) Reaction of sodium with alcohol

( Ethanol with sodium)

( Butan-1-ol with sodium)

( Butan-2-ol with sodium)

( 2-methylpropan-2-ol with sodium)

8) 2-methylpropan-1-ol
React with acidified Na2Cr2O7

React with metallic sodium

9) Ethanol can be used in a commercial cleaning agent, because it is a clear and colourless
liquid. Ethanol has the most exposed as the OH group attached on the most outside,
which is on the first carbon. Ethanol's hydroxyl group is able to participate in hydrogen
bonding, which explains how ethanol is a versatile solvent, miscible with water and with
many organic solvents. Moreover, the polar nature of the hydroxyl group causes ethanol
to dissolve many ionic compounds. The addition of even a few percent of ethanol to
water sharply reduces the surface tension of water, and therefore can be used to control
the viscosity of liquid detergents.

References
(1) Graham Hill, John Nolman, 2000, Chemistry In Context, 5 th ed. United
Kingdom: Thomas Nelson & Sons Ltd

[ Accessed on10 April 2015 ]

(2) John C . Kotz , Paul M . Treichel , John R . Townsend , 2012 , Chemistry And Chemical
Reactivity . 8th ed . London : Mary Frinch
[ Accessed on 10 April 2015 ]

(3) Cliffsnotes.2014.Reactions Of Alcohols. [ONLINE]


http://www.cliffsnotes.com/sciences/chemistry/organic-chemistry-ii/alcohols-andethers/reactions-of-alcohols
[ Accessed on 11 April 2015 ]

(4) Chemguide.co.uk.2003. Oxidations Of Alcohols. [ONLINE]


http://www.chemguide.co.uk/organicprops/alcohols/oxidation.html
[ Accessed on 11 April 2015 ]

(5) Gcsescience.com.2014.Alcohols- Reaction with sodium. [ONLINE]


http://www.gcsescience.com/o40.htm
[ Accessed on 11 April 2015 ]

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