Identification and Reaction of Alcohols

Chemistry lab report
Name : LIM JOE JEAN SCM029428
FIS JULY INTAKE
Experiment 1 : Identification and reaction of alcohols and phenol
Objective : To study the physical and chemical properties of alcohol and phenol .
Apparatus and materials : Test tubes , water bath , distilled water , ethanol, 2-propanol , t-
butanol , phenol , Lucas reagent , sulphuric acid , potassium dichromate , sodium metal ,
phenolphthalein indicator , iron (III) chloride (CAUTION : phenol is very corrosive , never handle
it with your bare hand . Wear glove . )
Procedure :
A) Solubility test
1. 5ml of water was added into four labeled test tubes . 1ml of each of the following
liquids was poured into the labeled test tubes and shake .
2. If the substances dissolves were observed , and your observation was recorded on the
table .
3. Test tube no 1 was labeled as ethanol , the following test tube no 2, 3, 4 were labeled as
2-propanol, t-butanol and phenol .
B) Lucas test
1) 1ml of ethanol , 2-propanol , t-butanol and phenol were added into four separated dry ,
labeled test tubes .
2) 3ml of Lucas reagent was added into each test tubes , then inserted an stopper and
shaked gently to mix .
3) The solutions were allowed to stand at room temperature for 15 minutes . The
appearances of cloudiness indicated a reaction.
4) If there is no visible change , the test tube were immersed into a water bath that
maintained at approximately 60 C for 15 minutes and observed whether any change
occurs . (to apply heating)
5) The observation was recorded in table.
C) Oxidation reaction of alcohol

1) 2ml of ethanol and 0.5 ml of sulphuric acid were added in a test tubes .
2) 0.5ml of potassium dichromate was added in the test tubes and heated in a water bath
for 15 minutes .
3) The odour and colour change occurred during test.
4) Step 1-3 were repeated using 2-propanol , t-butanol , phenol .
D) Iron (III) chloride test

1) 5 drops of sample were placed into separate clean , dry test tubes to be tested .
2) 2 drops of Iron (III) chloride solution were added into each test tube
3) Any changes in solution were noted . A purple colour indicated the presence of phenol.
4) The observation were recorded in table .
Results :
TEST ETHANOL 2-PROPANOL t-BUTANOL PHENOL
Solubility Soluble Soluble Soluble Insoluble
Lucas No changes After boiling , the Milky A layer of crystal

mixture become formed .
milky .
Oxidation Green (positive ) Light green at the Yellowish Black (positive )

top (positive) (negative)
Iron (III) chloride Not changes No changes No changes Turn to purple

Observation :
Discussion :
Solubility:
Alcohols are soluble in water. This is due to the hydroxyl group in the alcohol which is able to
form hydrogen bons with water molecules. Alcohols with a smaller hydrocarbon chain are very
soluble. As the length of the hydrocarbon chain increases, the solubility in water decreases.
With four carbon in the hydrocarbon chain and higher, the decrease in solubility becomes visible
as the mixture forms two immiscible layers of liquid. The reason why the solubility decreases as
the length of hydrocarbon chain increases is because it is requires more energy to overcome the
hydrogen bonds between the alcohol molecules as the molecules are more tightly packed
together as the size and mass increases. Ethanol and 2-propanol is easy to dissolve , In case of
tert-butyl alcohol the alkyl group is branched and has less surface area i.e. less hydrophobic and
hence more soluble in water. Indeed , t-butanol is the most miscible in water . Phenol is
insoluble in water because of the presence of benzene ring . The phenyl group in phenol is
nonpolar and hydrophobic so it is insoluble in water . (CAUTION : phenol is very corrosive , never
handle it with your bare hand . Wear glove . )
Lucas reagent :
Lucas' reagent is a solution of saturated and anhydrous zinc chloride in concentrated

hydrochloric acid. This test is used to distinguish between water-soluble primary, secondary,
and tertiary alcohols. Some alcohols react with ZnCl2 in an acidic aqueous solution to give an
alkyl chloride. The Lucas test involves a substitution reaction, where the –OH group of the
alcohol is replaced by a Cl atom. The Lucas reagent consists of a mixture of HCl and ZnCl2 that
are dissolved in water. The mechanism of this reaction involves a carbocation intermediate: first
an OH- ion is removed from the alcohol, leaving the carbon atom in the molecule positively
charged. Then a Cl- ion adds to the positively charged carbon atom. The result is the alcohol is
converted to a chlorinated alkane, with the Cl occupying the spot that the –OH was in. Since
tertiary carbocation are much more stable than primary or secondary carbonations, tertiary
alcohols will react readily with the Lucas reagent. Secondary alcohols will react slowly (usually in
5-10 minutes). Primary alcohols will not react much at all, since a primary carbocation is so
unstable. Therefore, Tertiary alcohols (t-butanol) react immediately .The test tube will get hot,
and because the chloride is insoluble two layers may be apparent, or a cloudy dispersion forms.
Secondary alcohols (2-propanol) will become cloudy in 5 to 10 minutes. After heating slightly,
gives the white layer within 10 min. Primary alcohols (ethanol ) give no reaction at all .Phenol
doesn’t react under Lucas test .
Oxidation :
Primary alcohols can be oxidized to either aldehydes or carboxylic acids depending on the
reaction conditions. Secondary alcohols are oxidised to ketones. Tertiary alcohols aren't oxidized
by acidified sodium or potassium dichromate(VI) solution. There is no reaction whatsoever. This
is because tertiary alcohols don't have a hydrogen atom attached to that carbon for the oxygen
to remove . In this experiment , potassium dichromate is added as an oxidizing agent to
determine whether the alcohol will undergo oxidation or not . potassium dichromate is an
orange-yellow solution. The orange-yellow color is due to the Cr O ion. The 2-oxidation number
of chromium is +6. This reagent will oxidize primary and secondary alcohols and, in turn,
becomes reduced. The chromium in dichromate is reduced to chromic ion, Cr . A greenish
colored solution results. This color change from orange-yellow to green serves as an indicator
for the presence of a primary or secondary alcohol. A primary alcohol is oxidized first to an
aldehyde, which will be further oxidized to an acid. For phenol oxidation , phenols are easily
oxidized despite the absence of a hydrogen atom on the hydroxyl bearing carbon . Hence ,
oxidized water become a dark brown color associated with increased toxicity . Through the
experiment ,ethanol , 2 propanol and phenol show positive result and undergoes changes of
color . Only t-butanol show negative result because it doesn’t show any color changes during the
experiment .
Iron chloride(III) test :
Iron chloride(III) is used to identify the presence of phenol . when Iron chloride(III) added into
phenol solution , it will form a violet complex which is intense colour .meanwhile other alcohol
such as ethanol , 2-propanol and t-butanol have no reaction , remain colourless when Iron
chloride(III) added.
Question :
1) Define the term of functional group

A functional group is a portion of a molecule that is a recognizable/classified group of
bound atoms. In organic chemistry it is very common to see molecules comprised
mainly of a carbon backbone with functional groups attached to the chain. The
functional group gives the molecule its properties, regardless of what molecule contains
it*; they are centers of chemical reactivity. The functional groups within a molecule
need to be identified when naming.
2) Draw the structure of a molecule that contains hydroxyl functional group .
3) Draw structuralof primary alcohol , secondary alcohol and tertiary alcohol .
4) Based on the observation , you made in this experiment , answer the following
questions .
i) What happenes to a phenol with iron (III) chloride reagent ?
Phenol turns to a purple/violet colour solution.
ii) What happenes to a tertiary alcohol with Lucas reagent ?
Tertiary alcohol (t-butanol) turns milky/cloudy .
Conclusion :
Ethanol is the primary alcohol ; 2-propanol is the secondary alcohol ; t-butanol is the tertiary
alcohol .

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Chemistry lab report

Name : LIM JOE JEAN SCM029428

FIS JULY INTAKE

Experiment 1 : Identification and reaction of alcohols and phenol

C) Oxidation reaction of alcohol

D) Iron (III) chloride test

TEST ETHANOL 2-PROPANOL t-BUTANOL PHENOL

Solubility Soluble Soluble Soluble Insoluble

Lucas No changes After boiling , the Milky A layer of crystal

Oxidation Green (positive ) Light green at the Yellowish Black (positive )

Iron (III) chloride Not changes No changes No changes Turn to purple

Lucas' reagent is a solution of saturated and anhydrous zinc chloride in concentrated

Iron chloride(III) test :

1) Define the term of functional group

3) Draw structuralof primary alcohol , secondary alcohol and tertiary alcohol .

i) What happenes to a phenol with iron (III) chloride reagent ?

Phenol turns to a purple/violet colour solution.

ii) What happenes to a tertiary alcohol with Lucas reagent ?

Tertiary alcohol (t-butanol) turns milky/cloudy .

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