CATHOLIC JUNIOR COLLEGE

H2 CHEMISTRY 9729

2019 PRACTICAL HANDBOOK – Part 5

Content
Page
9 Organic Chemistry

9.1 Organic Qualitative Analysis - Identification of Functional Groups 2

9.2 Organic Synthesis 8
9.3 Separation of two immiscible liquids 10

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 9 Organic Chemistry
9.1 Organic Qualitative Analysis - Identification of Functional Groups
Simple chemical tests to identify functional groups in organic compounds:

Test for Procedures Observations

Alkenes 1. Add 1-2 drops of Br2(aq) to 1 1. Orange Br2(aq) rapidly decolourised.
cm3 of organic compound.
Shake well after adding each
[Br2 adds across C=C bond of alkenes.]
drop of Br2(aq).
[electrophilic addition of alkenes]
- test for unsaturation. Relevant video of chemical test: https://tinyurl.com/y7jftf2a

2. Add 1-2 drops of acidified 2. Purple acidified KMnO4(aq) decolourised.

KMnO4(aq) to
1 cm3 of organic compound. Note: Methylbenzene, aldehydes and alcohols (1°, 2°) also give +ve test with hot acidified
Heat in water bath for 2-3 KMnO4
mins.
[oxidation of alkenes]
Halogenoalkanes 1. Add 1 cm3 of NaOH(aq) to 1 1. with R–Cl - white ppt of AgCl(s) observed;
R–X cm3 of organic compound. with R–Br - cream ppt of AgBr(s) observed;
Heat in water bath for 5
where R = alkyl, with R–I - yellow ppt of AgI (s) observed.
mins.
X = Cl, Br, I 2. Then add 1 cm3 of dilute [Dilute nitric acid is added to prevent precipitation of Ag2O (brown ppt).]
HNO3, followed by 2-3 drops
of AgNO3(aq). Relevant video of chemical test:
[hydrolysis, followed by https://tinyurl.com/test-for-halogenoalkanes (watch till 1:29 min)
precipitation]
Alcohols 1. Add 2-3 drops of acidified 1. with 1° alcohol - purple KMnO4(aq) decolourises; carboxylic acid formed
KMnO4(aq) to 1 cm3 of with 2° alcohol - purple KMnO4(aq) decolourises; ketone formed.
organic compound. Heat in
1° alcohol, RCH2OH with 3° alcohol - solution remains purple (no reaction).
water bath for 2-3 mins.
2° alcohol, R2CHOH [Purple MnO4– reduced to colourless Mn2+.]
[oxidation of alcohols]
3° alcohol, R3COH Note: Aldehydes also give +ve test with hot acidified KMnO4.
Video of oxidation of ethanol: https://goo.gl/ta8aqS
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 Test for Procedures Observations
Alcohols 2. Add 2-3 drops of acidified 1. with 1° alcohol - orange K2Cr2O7(aq) turns green; carboxylic acid formed
K2Cr2O7(aq) to 1 cm3 of with 2° alcohol - orange K2Cr2O7(aq) turns green; ketone formed.
organic compound. Heat in
1° alcohol, RCH2OH with 3° alcohol - solution remains orange (no reaction).
water bath for 2-3 mins.
2° alcohol, R2CHOH [Orange Cr2O72– reduced to green Cr3+.]
[oxidation of alcohols]
3° alcohol, R3COH Note: Aldehydes also give +ve test with hot acidified K2Cr2O7.
Relevant video of chemical test: https://tinyurl.com/dichromateinalcohol
3. Add 1 cm3 of ethanoic acid 2. A ‘pleasant’ characteristic smell of ester detected.
to 1 cm3 of organic
compound, followed by a few CH3CO2H + ROH  CH3CO2R + H2O
drops of conc. H2SO4. Heat
in water bath for 5 mins and Safety precaution: Use fume cupboard as conc. H2SO4 is very corrosive.
then pour into water. Note: This is not a preferred diagnostic test for alcohols because conc. H2SO4 is very
corrosive and the ‘ester smell’ may be subjective.
[esterification]

Phenols 1. Add 2-3 drops of neutral 1. Violet coloration observed.

FeCl3(aq) to
1 cm3 of organic compound.
Relevant video of chemical test:
[complex formation]
https://tinyurl.com/testforphenol (watch till 2:00 min)

2. To 1 cm3 of organic 2. Orange Br2(aq) decolourised;

compound, add Br2(aq) white ppt formed, and steamy fumes of HBr.
dropwise until in excess.
Shake well after adding each
drop of Br2(aq).
[electrophilic substitution]
Note: Phenylamine also gives the same observation.
Relevant video of chemical test: https://tinyurl.com/bromineinphenol

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 Test for Procedures Observations
Carbonyl 1. Add 2 cm3 of 2,4- 1. Orange ppt formed.
compounds dinitrophenylhydrazine
(Aldehydes & reagent to 1 cm3 of organic
Ketones) compound. If precipitate is
not formed immediately,
warm in water bath.
[condensation reaction]

Relevant video of chemical test: https://tinyurl.com/y8f4rhtt

Aldehydes 1. Add 1 cm3 of Tollens’ 1. Silver mirror formed on the side of the test tube.
reagent (ammoniacal silver
[Ag+ ions reduced to Ag.]
nitrate) to 1 cm3 of organic
compound. Warm in water
bath for 5 mins.
[oxidation of aldehydes]

Relevant video of chemical test: https://goo.gl/WNKs85

3
2. Add 1 cm of Fehling’s 3. Brick red ppt of Cu2O formed.
solution to 1 cm3 of organic
compound. Warm in water
bath for 5 mins.
[oxidation of aldehydes; not for
benzaldehyde]

Relevant video of chemical test: http://tinyurl.com/Fehling-solution

Carboxylic acids 1. Add a small spatula of 1. Brisk effervescence; colourless gas gives white precipitate with limewater. CO2(g)
NaHCO3(s) or Na2CO3(s) to evolved.
1 cm3 of organic compound.
RCO2H + NaHCO3  RCO2– Na+ + H2O + CO2
2. Bubble the gas evolved into
(effervescence)
limewater.
[salt formation]

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 Test for Procedures Observations
Acid chloride 1. Add 1 cm3 of AgNO3(aq) to 1 1. White ppt of AgCl formed.
cm3 of organic compound.
RCOCl + AgNO3  RCO2H + AgCl + HNO3
O [hydrolysis, followed by
precipitation]

C 2. Add 1 cm3 of ethanol to 1 2. A ‘pleasant’ characteristic smell of ester detected.

R Cl cm3 of organic compound. CH3CH2OH + RCOCl  RCO2CH2CH3 + HCl
Pour mixture into water.
Note: This is not a preferred diagnostic test for alcohols the ‘ester smell’ may be
[esterification]
subjective.

1. Add ½ spatula of organic 1. Pungent, colourless gas turns moist red litmus paper blue and gives dense white
compound to 5 cm3 of fumes (of NH4Cl) with conc HCl. NH3(g) evolved.
Primary
NaOH(aq). Heat in water
Amides O O
bath for 5 mins.
C NaOH(aq)
C
2. Test the gas evolved with R NH2 warm R O
-
+ NH3
moist red litmus paper. Dip a
glass rod in conc. HCl and
bring it close to the gas
evolved.
[hydrolysis of amide]
Phenylamine 1. To 1 cm3 of organic 1. Orange Br2(aq) decolourised;
Br
compound, add Br2(aq) white ppt formed, and
dropwise until in excess. steamy fumes of HBr. Br2 (aq)
NH2 Shake well after adding each NH2 Br NH2 + 3 HBr
drop of Br2(aq).
[electrophilic substitution] Br

White ppt
Note: Phenol also gives the same observation.

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 Test for Procedures Observations
Esters 1. Add 1 cm3 of NaOH(aq) to 1 1. Orange K2Cr2O7(aq) turns green.
cm3 of organic compound. [Orange Cr2O72– reduced to green Cr3+ only if the alcohol is primary or secondary.]
Heat in water bath for about
3 mins. [Hydrolysis of ester to give carboxylic acid and alcohol; followed by oxidation of
alcohol.]
2. Then add 2-3 drops of
acidified K2Cr2O7(aq) to the
resulting mixture. Heat in
water bath for 2-3 mins.

Iodoform test 1. Add 1 cm3 of NaOH(aq) to 1 1. Yellow ppt of CHI3 formed.

cm3 of organic compound.
for
Then add I2(aq) dropwise
until the colour of iodine
persists.
and alcohols with
Shake well after adding each
CH3CH(OH)– group
drop of I2(aq).
2. Heat in water bath for about
2 mins, and then add
NaOH(aq) dropwise to Relevant video of iodoform test: https://goo.gl/kAxGlQ
discharge the excess iodine.
Cool the mixture.

Flammable Corrosive Harmful / Irritant

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Safety Precautions

(1) Short chain organic compounds which are liquid at room temperature are usually volatile. They should be capped in bottles when not in use. Clean
up any spillage immediately to prevent spread of volatile vapour.

(2) Organic compounds are highly flammable. If heating is required, use a water bath instead of direct heating using a naked flame.

 X
Heating using hot Do NOT heat using a naked
water bath flame.

(3) If acidic fumes e.g. HCl or HBr are liberated, perform the experiment in the fume cupboard and wear goggles to protect eyes from the fumes.

(4) If alkaline gas is liberated, wear goggles to protect eyes from the fumes. Take care not to bring the mouth of test tube too close to your nose.

(5) Take care when handling corrosive chemicals; e.g. concentrated acids. Wear gloves so as to avoid direct contact.

(6) Take care when handling chemicals that are “harmful/irritant” as they may cause reddening or blistering of the skin. Avoid direct contact.

(7) After completing each chemical test, dispose of the chemicals in proper waste containers (usually placed in fume cupboard). Do not flush them
down the sink, as some organic compounds are toxic/corrosive.

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9.2 Organic Synthesis
Set up used for organic synthesis Methods used for purification: Methods used for purification:
2. Recrystallisation (to collect solid)
1. Heating under reflux
1. Distillation(to collect liquid)

Many organic reactions are quite slow and Steps for recrystallisation:
require heating to achieve a reasonable
reaction rate. Most organic chemicals are 1. Dissolve solids in minimum amount of hot
quite volatile, and they will evaporate and be Distillation separates the component solvent.
lost when heated. substances from a liquid mixture as different 2. Filter the solution quickly while hot.
liquids boil off at different temperatures. 3. Cool hot filtrate (in ice bath).
Heating under reflux allows the vapour to 4. Collect crystals using vaccum filtrate
cool down at the surface of the condenser, The distillate is then collected once the vapour (Buncher funnel).
condense back to liquid state and drip back condenses. 5. Dry crystals between layers of filter
into the flask. paper/ under infra-red lamp.
https://youtu.be/7g4e3dhtgjI?t=277
https://youtu.be/b6xFAEkjmGg * To check for purity: Pure solids melt sharply/
over a small range of temperature *
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9.3 Separation of two immiscible liquids

In order to separate immiscible liquids (liquids that do not dissolve in each other), a separating funnel
is used. This technique is useful in separating organic products from an aqueous reaction mixture.
This technique is also useful in determining the partition coefficient, K, of an organic compound in

water. Partition Coefficient, K =

Watch this video to find out how to use a separating funnel

https://youtu.be/BQMzcfw8w6w

Procedures

Diagram from http://wwwchem.uwimona.edu.jm/lab_manuals/c1901exp8.html

1. Pour the two immiscible liquids into the separating funnel. Shake the mixture in the separating
funnel and ensure that the pressure in the funnel should be periodically released.

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2. Support the separating funnel using a retort stand. Then, please a clean conical flask below the
separating funnel.
3. Allow it to stand and wait for the liquids to separate completely. The denser liquid will be the
bottom layer.
4. Open the tap of the funnel to allow the bottom layer to drain into the conical flask. Close the tap
before the top layer of liquid runs out.
5. Invert the separating funnel to allow the top layer of liquid to be collected in another clean
conical flask.

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