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QUICK REVISION SHEET FOR A2 CHEMISTRY (UNIT VI )


Thermal decomposition of metal compounds:- Less reactive metal compounds (Lithium and group 2) decompose on
heating. More reactive metals (group 1) dont decompose on heating and thermally stable.
Group 1 carbonates:- They don't decompose on heating.
Lithium and group 2 Carbonates:- Metal carbonates decompose on heating to give metal oxide and Carbon dioxides.
CaCO3 CaO + CO2
Lime (CaO) dissolves in water to form lime water [(Ca(OH) 2].
Group 1 nitrates:- They partially decompose on heating to give metal nitrite and Oxygen.
2KNO3 2KNO2 + O2
Lithium and group 2 nitrates:- They decompose on hating to give metal oxide, nitrogen dioxide (brown gas) and
Oxygen.
2Mg (NO3) 2 2MgO + 4NO2 + O2
Flame Test:- Add a few drops of concentrated HCl to powdered salt and pick up a small sample on Nichrome wire. Hold
the wire in Bunsen burner and note the flame colour.
Cation Flame colour
Sodium ion Yellow
Potassium ion Lilac
Barium ion Green
Magnesium Colourless
Calcium Brick red
Lithium Red
Strontium Red
Tests for Lithium and Group 2 cations with Sodium hydroxide
TEST Observation Result
Add Sodium hydroxide solution White precipitate (Ca(OH)2 Lithium and group 2 ions
Tests for Ammonium ion (NH4+)
Test Observation Result
Add aqueous Sodium hydroxide Pungent smell. The gas produced Ammonium ion (NH4+)
(NaOH) and warm turns damp red litmus paper blue Ammonia gas (NH3)
Tests for Sulphate, Sulphite and Carbonate ions
TEST Observation Result
Add dilute White precipitate (BaSO4) Insoluble in dilute HCl Sulphate ion (SO42-)
Hydrochloric White precipitate (BaSO4) dissolves in dilute HCl Sulphite ion
acid, then add Sulpur dioxide gas is produced on warming which turn (SO32-)
aqueous Barium acidified Potassium dichromate (VI) orange to green
chloride [Ba(Cl2)] White precipitate (BaSO4) Carbonate ion
Dissolves in dilute HCl with effervescence (CO32-)
Tests for Halide ions
TEST Observation Result
Add a few drops of White precipitate (AgCl ), darken in sunlight Chloride ion (Cl-)
dilute Nitric acid and soluble in aqueous ammonia
(HNO3) and then add Cream precipitate (AgBr) , darken in sunlight and Bromide ion (Br-)
aqueous Silver nitrate soluble in Concentrated ammonia
(AgNO3) Yellow precipitate (AgI) insoluble in ammonia Iodide ion (I-)
Reaction of Metal halide with concentrated Sulphuric acid
Observation on adding concentrated Sulphuric acid Result
Steamy fumes (HCl) Chloride ion
Steamy fumes (HBr), Brown vapours (Br2), Colourless gas which turn acidified Bromide ion
Potassium dichromate orange to green (Redox reaction)
Steamy fumes (HI), Black solid, Purple vapours (I2), rotten egg smell (H2S), Iodide ion
Yellow solid (S) (Redox reaction)
MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)
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Tests For Gases


Test Observation Result
Glowing splint Relights Oxygen gas (O2)
Lime water Turns milky Carbon dioxide gas (CO2)
Damp red litmus paper Turns blue Ammonia gas (NH3)
Acidified Potassium dichromate (VI) solution Orange to green Sulphur dioxide (SO2)
Lighted splint Goes pop Hydrogen
Blue anhydrous Cobalt (II) chloride Turns pink Water vapours
Steamy fumes on exposure to moist air, blue litmus paper turns red Hydrogen chloride
Brown gas Bromine, Nitrogen dioxide
Purple vapours, dark brown solution, black solid Iodine
Water vapours or steam is given out on heating Hydrated salt
Acid Base Indicators
Indicator acidic solution Alkaline solution Neutral solution
Litmus paper Blue litmus paper turns red Red litmus paper turns blue No change
Phenolphthalein Colourless Pink Pale pink
Methyl Orange Red Yellow Orange
Universal indicator Red Blue Yellow green
Chemical Test for Water:-
i) Add water to anhydrous Copper (II) sulphate, colour changes from white to blue.
ii) Add water to anhydrous Cobalt (II) chloride, colour changes from blue to pink.
Tests for Alkene
Test Observation Result
Add aqueous Bromine and shake Yellow solution is decolorized Alkene
Add acidified Potassium manganate (VII) Purple solution is decolorized Alkene
solution and shake
TESTS AND OBSERVATIONS OF TRANSITION METAL IONS
Transition metal salts are coloured and form coloured solution in water. Non-transition are white solids and form
colourless solution in water.
If a salt dissolves in water with a pH 6.0, then hydrolysis or deprotonation reaction has occurred.
Aqua Ion Color Few drops of alkali Excess Few drops of NH3(aq) Excess NH3(aq)
Ion NaOH(aq) NaOH(aq)
Fe2+ Pale green Dark green ppte Insoluble in Dark green ppte Insoluble in excess
Fe(OH)2(H2O)4 excess Fe(OH)2 because Fe(OH)2 is not
Surface turns brown Surface turns brown due amphoteric, no further
due to oxidation of Fe2+ to oxidation of Fe2+ ion deprotanation occurs
ion to form to form Fe(OH)3(H2O)3 & ligand exchange
Fe(OH)3(H2O)3 reaction occur
Fe3+ Yellow / Rusty red brown ppte Insoluble in Rusty red brown ppte Insoluble in excess
brown Fe(OH)3 excess Fe(OH)3
Mn2+ Pink Cream / brown ppte Insoluble in Cream / brown ppte Insoluble in excess
Mn(OH)2 excess Mn(OH)2
Cu2+ Blue / Blue ppte Insoluble in Blue ppte Deep blue solution
green Cu(OH)2 excess [Cu(OH)2(H2O) 4] [Cu(NH3)4 (H2O) 2]2+
Ni2+ Green Green ppte Insoluble in Green ppte Blue solution
Ni(OH)2 excess [Ni(OH)2 (H2O)4] [Ni(NH3)4 (H2O) 2]2+
3+
Cr Green Green ppte Green solution Green ppte Green solution
[Cr(OH) 3 (H2O)3] [Cr(OH) 6]3- [Cr(OH) 3 (H2O)3] [Cr(NH3) 6]3+
Zn2+ Colourless White ppte Colourless White ppte Colourless solution
Zn(OH)2 solution [Zn(OH)2 (H2O)4] [Zn(NH3)4 (H2O) 2]2+
4-
[Zn(OH)6]

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Ligand exchange reactions:- The ligands that bond more effectively to transition metal ions give more stable complexes.
The reaction results in a color change due to different amount of splitting between d orbitals.

Pale blue deep blue


[Cu (H2O)6]2+ + 4Cl- [CuCl4]2- + 6 H2O
Blue green
The Copper (I) iodide is white precipitate (CuI). Iodine (I 2) or (I3-) forms brown solution in water.
Chemistry of Chromium:-

Step 3 is not a redox process because chromate and dichromate both have same oxidation number (+6).
Reaction 1 is ligand exchange and reagent needed in concentrated HCl.
In Reaction 4, green ppte reacts to form green solution because NaOH is a strong alkali and [Cr(OH) 3 (H2O)3] loses three
protons because it is amphoteric. To reverse reaction 4, add acid.
In Reaction 6, entropy increases due to increase in number of particles.

[Cr(H2O) 6]3+ ion react with water to form acidic solution.

The pH of aqueous solution of [Cu(H2O) 6]2+ ion is higher than [Cr(H2O) 6]3+ because concentration of oxonium ion is less
because Copper ion in Cu2+ and Chromium ion is Cr3+.

Color of Chromate and dichromate ions:-


Color of Chromate ion (CrO42-) is yellow and dichromate ion (Cr2O72-) orange.

Sodium chromate (VI) is a yellow solid and Sodium dichromate (VI) is orange solid.
Redox titration of Potassium manganate (VII) and Iron (II) ions:- A burette was filled with Potassium manganate
(VII) solution up to 0.0cm3 mark. Using a pipette, 25cm3 of colourless Iron (II) solution was poured into a conical flask
and a test tube of Sulphuric acid is added. Sulfuric acid is added in large excess to ensure that the manganate (VII) ions
were fully reduced to manganese (II) and large number of H+ ions is required in titration. The potassium manganate (VII)
solution was added from the burette until first permanent pink color is seen. The titration is self indicating, so no
additional indicator is needed. It is incorrect to use Hydrochloric acid instead of dilute Sulfuric acid because HCl will be
oxidized to Chlorine by the manganate (VII). So, the reaction of the Iron (II) ions with manganate (VII) will not be
quantitative and titre will be too high.
Calculations:- MnO4- + 8H+ + 5Fe2+ Mn2+ + 5Fe3+ + 4H2O
Redox titration of Sodium dichromate (VI) and Iron (II) ions:- The concentration of a solution of sodium
dichromate(VI), Na2Cr2O7, can be found by titration with a solution containing Fe 2+ (aq) ions in acidic conditions. A 20.0
cm3 sample of a solution of sodium dichromate (VI), of unknown concentration, was titrated with a solution of Fe 2+(aq)
ions, of concentration 0.0500 mol dm3. An indicator, diphenylamine, was used. This turned an intense violet colour at the
end point.

MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)
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Function of indicator:- The indicator makes end point more obvious, sharper and easier to see.
Effect of air bubble in the tip of burette:- Titre would appear to be greater because extra solution needed to fill ate air
gap. So, calculated concentration would be greater than actual value.
Pipette and measuring cylinder:- Pipette is used for exact measurement of solution and measuring cylinder is used for
approximate volume measurement.
Analysis of Copper content in old coins:- Some old coins with a high copper content were analyzed as follows.
Procedure:-
1. The coins were weighed and dissolved in concentrated nitric acid, producing a solution which contained copper(II)
nitrate.
2. The solution containing copper(II) nitrate was neutralized by adding sodium carbonate solution until a precipitate of
copper(II) carbonate just appeared. Dilute ethanoic acid was then added, drop by drop, until the copper (II) carbonate
precipitate just dissolved.

3. The solution containing copper(II) nitrate was transferred to a volumetric flask and made up to 250 cm 3 with distilled
water.
4. 25 cm3 portions of this solution were transferred to separate conical flasks. Then 10 cm3 of 1.0 mol dm 3 potassium
iodide (an excess) was added to each flask.
5. The liberated iodine was titrated with 0.125 mol dm3 sodium thiosulfate solution.

Redox titration of Iodine and Sodium thiosulphate:- A burette was filled with Sodium thiosulphate up to 0.0cm3 mark.
Using a pipette, 25cm3 of colourless aqueous Potassium iodate solution was poured into a conical flask. Excess Potassium
iodide and dilute Sulphuric acid were added to the flask and the mixture shaken. The chemicals reacted to form Iodine.
The Sodium thiosulphate solution was added from the burette 1cm3 at a time. When the color of mixture was pale
yellow, starch solution was added to the flask. Sodium thiosulphate solution was then added until the solution became
colourless. Starch is not added initially because it forms insoluble starch-iodine complex.
The burette is rinsed with solution to remove impurities. Starch indicator shows accurate colour change from blue-black to
colourless.
Sodium hydrogen carbonate is used to neutralize excess acid. The iodine concentration is proportional to the volume of
Sodium thiosulfate solution added. When titres are small, percentage error will be high.
Calculations:- I2 + 2Na2SO3 2NaI + Na2S4O6 IO3- + 5I- + 6H+ 3I2 + 3H2O
i) Moles of Sodium thiosulphate solution = Concentration volume
ii) Moles of Iodine = answer to (i) / 2
iii) Moles of Potassium iodate = answer to (ii) / 3
iv) Concentration of Potassium iodate (V) in mol dm-3= answer (iii) / volume in dm3
v) Concentration of Potassium iodate (V) in g. dm-3= answer (iv) molar mass
Methods to monitor change in concentration of Iodine:-

1) Colorimetry because Iodine is coloured.


2) Conductivity because increase in concentration of ions.
3) pH due to increase in concentration of H+ ions.
4) Acid base titration due to increase in concentration of H + ions.
5) Silver nitrate titration due to due to increase in concentration of I - ions.
First order reaction for propanone:- On doubling concentration of propanone keeping other concentrations in rate equation
constant, rate doubles.
Zero order graph for Iodine:- The graph is a straight line, gradient is constant and rate stays constant as Iodine used up.
So, Iodine is not involved in the rate determining step. It is not necessary to calculate the actual concentration of Iodine
because concentration of Iodine is proportional to titre.
The propanone and the hydrochloric acid are used in large excess in the reaction so that
propanone and Hydrogen ion concentrations are approximately constant during reaction and
order observed is therefore that of the Iodine alone.

MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)
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The titration is done immediately after they have been withdrawn from the reaction mixture because propanone only
slows down reaction but does not stop. So, if flask is left, titre would be too low.

Reaction of bromoethane and hydroxide ions:-

K = (1.54 10-6) / (0.1 0.15)


= 1.54 10-6 mol-1 dm3+ s-1
So, Order of reaction = 2
In an experiment to investigate the hydrolysis, a solution of 2-chloro-2-methylpropane in aqueous ethanol was
prepared at room temperature. The pH of this solution was measured at intervals using narrow-range pH paper. The
reaction occurring is

The initial pH is 7 because no acid is present and only water is present.

The pH rapidly falls to 2 or lower because Hydrolysis is rapid in the absence of


(added) hydroxide ions and only water is present. Thus [OH-] does not affect the rate.

Equation for rate determining step.


MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)
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So, order of reaction is 1.


TESTS for ALDEHYDE & KETONES
Test Observation Result
Add Bradys reagent Orange precipitate Both Aldehyde or ketone
(2,4-dinitrophenol hydrazine) (2,4-dinitrophenol hydrazone present
derivative of carbonyl compounds)
Boil with Fehlings or Benedicts Blue solution gives red precipitate Aldehyde present
2+
solution (Reduction of Cu to Cu2O) Ketone absent
Heat with Tollens reagent Silver mirror formed Aldehyde present
(ammonical silver nitrate solution) (Reduction of Ag+ to Ag) Ketone absent
Add acidified Potassium Orange to green solution Aldehyde or ketone is present
dichromate solution (Reduction of Cr(VI) toCr(III)
Iodoform Test for ethanol, ethanol, methyl secondary alcohol & ketone:- Organic compound with a methyl group
attached to functional group give a yellow precipitate of iodoform (CHI 3) with an antiseptic smell, when organic
compound is reacted with a solution of Iodine in Sodium hydroxide.
Esterification:- Carboxylic acid with alcohol in presence of concentrated Sulphuric acid catalyst to form ester and water
by heating in water bath. The reaction is reversible and does not go to completion. The smell of an ester is fruity or glue
like. Tap funnel is used to wash impure product.
Ethanoic acid + Propanol Propyl ethanoate + Water
CH3 COOH + CH3- CH2-CH2-OH CH3 COOCH2- CH2-CH3 + H2O
This reaction is quite slow. If propanoic acid is replaced propanoyl chloride or propanoic anhydride, then ester forms at a
faster rate.
Tests for Alcohol & Carboxylic acid:-
Test Observation Result
Add Sodium Bubbles of gas Alcohol
White solid formed (Sodium ethoxide)
Sodium disappears
Add Phosphorous Steamy fumes of HCl which turn damp blue litmus Hydroxyl group (OH) in
(V) chloride (PCl5) paper red or form white smoke with ammonia alcohol and carboxylic acid
Neutralization Reactions of Carboxylic acid:- Carboxylic acid reacts with metal carbonate or Hydrogencarbonate to
form salt, water and Carbon dioxide. The observation is bubbles of gas or fizzing.
Optical Activity:- A chiral Carbon atom has four different atoms or groups attached. A chiral centre in a molecule gives
optical isomers, able to rotate the plane of polarization of plane polarized monochromatic light e.g., butan-2-ol.
Tests for primary and secondary Alcohol
Test Observation Result
Add acidified Potassium Orange to green solution Primary or secondary alcohol
dichromate solution
Incomplete oxidation of primary alcohol:- Incomplete oxidation of primary alcohol produces aldehyde. Fewer amounts
of potassium dichromate and dilute sulphuric acid are used. The apparatus used is simple distillation.
Complete oxidation of primary alcohol:- Complete oxidation of secondary alcohol produces organic acid. Excess
amount of potassium dichromate and concentrated sulphuric acid are used. The apparatus used is heat under reflux.
Oxidation of secondary alcohol:- The oxidation of secondary alcohol produces ketone using heat under reflux.
Test for Phenol:- Add Bromine water. The Color changes from brown to colourless, misty (steamy) fumes formed and a
white precipitate is formed.
Tests for Halogenoalkane
TEST Observation Result
Add aqueous Silver White precipitate (AgCl ), darken in sunlight Chloride ion (Cl-)
nitrate (AgNO3) to and soluble in aqueous ammonia
solution of Cream precipitate (AgBr) , darken in sunlight Bromide ion (Br-)
halogenoalkane in and soluble in Concentrated ammonia
ethanol solvent Yellow precipitate (AgI) insoluble in ammonia Iodide ion (I-)

MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)
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Recrystallization:- Dissolve impure solid in minimum volume of hot solvent to prevent much of the product remaining
in solution on cooling. Filter whilst hot using preheated funnel to avoid crystallization, allow to cool and filter off product.
Wash with small amount of cold solvent to remove soluble impurities and then dry. Recrystallization reduces yield
because some product remains in solution, solid remaining on filter paper and in funnel.
Desiccator:- The solids can be dried in a desiccator to avoid decomposition of solid. The solid may decompose or melt if
heated in an oven.
Steam Distillation:- Steam is passed into the mixture and product vapors distilled off with the water and condensed. The
product distils at a lower temperature which prevents decomposition.
How to obtain dry oil from a mixture of water and clove oil:- Mix organic solvent and oil-water mixture in a separating
funnel and then separate. (Add saturated solution of Sodium chloride and separate in a separating funnel). Add anhydrous
Calcium chloride to clove oil and then filter.
Buchner funnel:- The solid can be dried by filtration under reduced pressure using Buchner funnel. The reduced pressure
is achieved by flow of water through pump. The suction filtration is faster than normal filtration.

Determination of melting and boiling temperatures:- The pure liquids boil within a range of 1-2oC. The boiling
temperature of liquid varies with the external pressure, so it is not satisfactory method to access purity of a substance. The
pure solid melt within a range of 1oC. The melting temperature is a reliable method to access purity because it will not
change. The pure substance has a sharp melting temperature, so compare experimental value to data book value.

Washing:- The unwanted impurities can be removed by shaking reaction products with water or sodium carbonate
solution. The carbonate reacts with excess acid present and releases Carbon dioxide gas. The acid will be neutralized
when no more fizz.
MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)
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Drying:- The organic products contain traces of water from the aqueous reagents. The liquids can be dried by being left in
contact with drying agent like silica gel, anhydrous Calcium chloride, anhydrous Sodium sulfate and anhydrous
Magnesium sulfate. The dry product is separated by decanting.
Distillation:- It is used to separate solvent from a solution. The solvent boils off as a gas at its boiling point. The gas
condenses back to a liquid in the cool condenser. The solute remains n the flask. It is used to get pure water from salt
solution. e.g., Water from sea water, Water from Copper (II) sulphate solution and Water from Magnesium sulphate
solution. The liquid should be collected within a boiling range of 1-2 oC to remove impurities. The impurities are left
behind in the flask due to their high boiling point.
Anti-bumping granules:- These granules avoid formation of large bubbles, liquid rising up to the condenser, shooting
out of the top and uneven boiling.
Hydrolysis of Acyl chloride:- The reaction of acyl chloride with water produces carboxylic acid vigorously at room
temperature. The reaction route is not sensible because acyl chloride is more expensive than acid.
Fractional distillation:- It is used to separate two or more miscible liquids with different boiling points. . The organic
compound with a lower boiling point would be collected first in the beaker at its boiling point. The temperature of
thermometer would rise when organic compound with a higher boiling point began to be collected. e.g., To separate a
mixture of ethanol & water from fermented liquor, Nitrogen & Oxygen from liquid air, different petroleum fractions from
crude oil, methanol & ethanol. Electric heater is used to heat organic compounds because they are flammable.
Solvent extraction and separation of immiscible liquids by Separating Funnel:- Organic compounds have different
solubilities in different solvents. The products can be concentrated in one layer using two immiscible solvents. The layers
are separated by separating funnel. The iodine is more soluble in hexane than water, so it can be separated by this method.

Heat under Reflux:- It is used to increase speed of reaction because organic reactions are slow and involve breaking of
covalent bonds. Organic reactions require prolonged heating and refluxing allows organic mixtures to boil for a long time.
It also prevents loss of vapours by evaporation. The mixture being heated returns to the flask. The vapours are cooled and
condensed back in same flask.

Method of Chromatography:- (Separation of mixture of organic compounds from ethanol washings)


Add a small drop of ethanol washings on a datum line near the bottom of the plate covered with a layer of silica. Then, put
plat in a sealed container with the suitable solvent below the spot. Leave until the solvent has moved to the near of the top
of the plate.
Improvement of Chromatogram:- Add pure samples of organic compounds to chromatogram and get two spots at different
levels corresponding to pure samples. (Measure Rf value on chromatogram of washings and compare with Rf of pure
samples).

SAFETY PRECAUTIONS
MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)
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Safety Precaution Reason


Do experiment in Fume cupboard Toxic fumes of Bromine, methanol or
chloroalkane, Benzene
Wear gloves Strong acid and alkali are corrosive
Pentane or propan-1-ol are irritant
Benzene is toxic by skin absorption
Wear overall or safety goggles For protection of clothes and eyes
Use water bath or electric heater for heating organic Organic compounds (ethanol, benzene,
compounds nitrobenzene) are flammable, so dont heat by
Bunsen burner or naked flame.
The condenser water flow should be right way round, The jacket should be full of water so that
lower level water in and upper level water out. cooling will be effective
Effect of Heat on Solids
Change RESULT
Sublimation Ammonium salt, Iodine
Water given out on heating Hydrated salts
Acidic gas Hydrogen chloride Hydrated ammonium chloride
Damp red litmus paper turns blue (Ammonia gas) Ammonium salts
NMR spectrum of propanal (CH3CH2CHO):- There will be three peaks because Hydrogen in 3 different environments.
The splitting pattern (5, 3, 3) is consistent with propanal and inconsistent with propanone, which would have only one
peak.

Preparation of Organic Compound 2-ethanoylaminobenzoic:- The compound 2-ethanoylaminobenzoic acid can be


made by reacting 2-aminobenzoic acid with ethanoic anhydride.

The steps of the experimental procedure are as follows:


1. Measure out 4.00 g of 2-aminobenzoic acid into a pear-shaped flask. Add ethanoic anhydride.
2. Add anti-bumping granules to the flask, fit a reflux condenser and bring the mixture slowly to the boil. Heat under
reflux for 15 minutes.
3. Allow the reaction mixture to cool and add 5 cm3 of water. Bring the contents of the flask back to the boil and then
remove from the heat.
4. Let the reaction mixture cool to room temperature. A pale brown crystalline solid will form.
5. Collect the solid by suction filtration.
6. Purify the solid by recrystallization using ethanoic acid as the solvent.
7. Determine the melting temperature of the dry solid.
Preparation of methyl 3-nitrobenzoate:- A student attempted to make a sample of methyl 3-nitrobenzoate using the
following
MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)
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reaction.

Procedure
1. Transfer 9 cm3 of concentrated sulfuric acid into a 100 cm3 conical flask and cool it to below 10 oC in an ice bath. Add
5.0 g of methyl benzoate, swirling the flask. Mix 3 cm3 of concentrated nitric acid with 3 cm3 of concentrated sulfuric
acid in another small flask and cool it in ice.
2. Add the mixture of nitric and sulfuric acids, drop by drop, to the methyl benzoate solution, making sure that the
temperature stays below 15oC.
3. Take the mixture out of the ice bath and leave it to stand for 10 minutes at room temperature. Pour the mixture over 40
g of crushed ice and collect the solid product by filtering the mixture under suction. Wash the precipitate, first with cold
water, then with ice-cold ethanol. Keep the washings obtained with the ethanol for a further experiment.
4. Purify the impure methyl 3-nitrobenzoate by recrystallization, using ethanol as the solvent, cooling the solution in an
ice bath to assist recrystallization.
5. Dry the recrystallized product and determine the yield.
Preparation of N-phenylethanamide:- N-phenylethanamide may be prepared in the laboratory by reacting ethanoic
anhydride with phenylamine; both the reactants and the products are flammable. The equation for the reaction is shown
below.

The steps of the experimental procedure are as follows.


1. Mix the amount of ethanoic anhydride calculated in (a) with 10g of glacial (pure) ethanoic acid in a round-bottom flask
and add a further 1g of the ethanoic anhydride to ensure that all phenylamine reacts.
2. Cool the flask from step 1 in a beaker of cold water and add 9.00g of phenylamine, drop by drop, with gentle shaking
because reaction is exothermic.
3. Add anti-bumping granules and reflux the mixture from step 2 for 30 minutes.
4. Pour the liquid from the reflux flask into a beaker containing 100cm3 of distilled water and allow the mixture to stand
until no more crystals are formed.
5. Filter the crystals under reduced pressure using a Buchner funnel and flask, washing the crystals with cold water.
6. Transfer the crystals to a boiling tube and dissolve them in the minimum volume of boiling water. Filter the hot solution
using a glass filter funnel, cool the filtrate in a beaker of ice-cold water and filter the crystals formed using a Buchner
funnel and flask. The yield is less than 100% due to transfer looses because some of the N-phenylamide will remain
on the filter paper and in solution. Some will be deposited on the sides of glassware. If the yield is greater than
100%, then product was not dry.
7. Dry the crystals between filter papers and then by storing them in a desiccator.
8. Weigh the dry crystals and calculate the yield.

Preparation of Azo dye:- Azo dyes are made in large quantities from benzene, C6H6, via nitrobenzene, C6H5NO2, and
phenylamine, C6H5NH2. The preparation of nitrobenzene requires benzene to be warmed under reflux at about
55C with a mixture of concentrated nitric and sulfuric acids. Some information about these substances is given below:
Benzene: immiscible with water; highly flammable; extremely toxic by ingestion or inhalation; known carcinogen.
MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)
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Concentrated nitric acid: miscible with water; causes severe burns to eyes and skin; strong oxidizing agent. The acid
contains about 30% water by volume.
Concentrated sulfuric acid: miscible with water; causes severe burns to eyes and skin; strong oxidizing agent; dilution
with water is very exothermic and can be dangerous.
Nitrobenzene is then reduced to phenylamine, C 6H5NH2, and the phenylamine is diazotized by reaction with nitrous acid
at a temperature between 0C and 10C. Nitrous acid is generated in the reaction mixture from sodium nitrite and
hydrochloric acid. Reaction of the diazonium compound with an alkaline solution of a phenol will produce a solid azo
dye, which is purified by recrystallization.
Purification by recrystallization requires the following steps:
1. The azo dye is dissolved in a minimum volume of hot solvent.
2. The solution is filtered hot through a pre-heated funnel.
3. The solution is cooled and filtered using a Buchner funnel.
4. The solid is washed with a small amount of cold solvent.
5. The solid is dried in a desiccator.
Conversion of Phenylamine into benzenediazonium cation:- The reagents used are Sodium nitrite and Hydrochloric
acid to make Nitrous acid. The nitrous acid is made in this reaction because it is untable and decomposes at room
temperature, so it cant be stored. The reaction is carried out at a temperature of 0-10 oC. The rate of reaction will be too
slow at a lower temperature and diazonium ion decomposes at higher temperature.
Esterification:- Propyl ethanoate is an ester which has a smell similar to that of bananas or pears. It
can be made in the laboratory from propan-1-ol and ethanoic acid. The equation for the
reaction is

Procedure
1. Propan-1-ol (50 cm3) and ethanoic acid (50 cm3) are mixed thoroughly in a 250 cm3 round-bottomed flask.
2. Concentrated sulfuric acid catalyst (10 cm3) is added drop by drop to the mixture, keeping the contents of the flask
well-shaken and cooled in an ice-water bath to prevent splashing of acid, getting mixture too hot and loss of volatile
compounds.
3. When the acid has all been added, a reflux condenser is fitted to the flask to prevent loss of volatile substances and the
mixture gently boiled over an electric heating mantle for about 30 minutes because reaction is slow.
4. The mixture is cooled, and the apparatus rearranged for distillation. The crude ester (about 60 cm 3) is distilled off. The
impurities can be water, propan-1-ol, ethanoic acid and sulfuric acid.
5. The distillate is placed in a separating funnel and shaken with about half its volume of 30% sodium carbonate solution,
with the pressure being released at intervals. The pressure is due to Carbon dioxide gas produced by the neutralization of
acid with sodium carbonate solution. The lower aqueous layer (due to higher density) is then discarded.
6. The crude ester is shaken in a separating funnel with about half its volume of 50% calcium chloride solution, which
removes unreacted alcohol. The lower layer is discarded.
7. The ester is run into a clean, dry flask containing some anhydrous calcium chloride and swirled. The drying agent
removes water and product becomes clear.
8. The ester is filtered into a clean, dry flask, with a few anti-bumping granules, and distilled. The fraction boiling
between 100C and 103C is collected.

MASHKOOR HUSSAIN (M.Sc CHEMISTRY) CERTIFIED CHEMISTRY TEACHER FOR A LEVEL CHEMISTRY (JARIS)

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