Edexcel GCE
Chemistry
Advanced
Unit 6B: Chemistry Laboratory Skills II Alternative
Paper Reference
6CH08/01
Reagent Use Example
KMnO4H+ (aq) Oxidation C6H5CH3 → C6H5CO2H
MnO2 Oxidation C6H5CH3 → C6H5CHO
CrO3 Oxidation C6H5CH3 → C6H5CHO
K2Cr2O, H+ (aq) Oxidation RCH2OH → RCHO
Na2Cr2O7, H+ (aq) (Add oxidant slowly to hot alcohol, and distil
off aldehyde as fast as it is formed.)
RCH2OH → RCO2H
(Reflux the mixture until oxidation is
complete)
MnO4 (neutral) Oxidation
Reflux C6H5 C X → C6H5CO2H
(where X = CH3, CH2OH etc.)
KMnO4, conc, hot Oxidation of RCH = CHR’ → RCHO + R’CHO
alkenes to
determine
position of C = C
bond
H2, Pt Reduction C6H5NO2 → C6H5NH2
NaBH4 (aq) Reduction of RCHO → RCH2OH
C = O, not C = C R2C = O → R2CHOH
Sn + HCl (aq) Reduction C6H5NO2 → C6H5NH2
H2,Ni Reduction of R R
C = C, not C = O
C = CH C = O → CH CH2 C=O
C C → CH2CH2
RCN → RCH2NH2
Hydrogenation of oils to form fats
LiAlH4 (ether) Reduction of RCO2H → RCH2OH
C = O, not C = C RCO2H’ → RCH2OH
RCONH3 → RCH2NH2
Br2 (organic solvent) Test for RCH = CHR’ → RCH CHR’
unsaturated
Br Br
(not HBr evolved)
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Reagent Use Example
KMnO4, OH- (aq) Test for RCH = CHR’ → RCH CHR’
unsaturated
OH OH
NaOH, I2 Iodoform test
for CH3CO or CH3CHO + I2 + NaOH → CHl3
CH3CH (OH)
+
NaNO2, H+ (aq), < 10oC Diazotisation C6H5NH2 → C6H5N ≡N
Al2O3 Dehydration C2H5OH → CH2 = CH2
Hot conc. H2SO4 Dehydration RCH(OH)CH3 → RCH = CH2
Conc. H2SO4 Esterification ROH + R’CO2H → R’CO2R + H2O
Cold conc. H2SO4, Hydration RCH = CHR’ → RCH CHR’
then H2O
H OH
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H+ (aq)
PCl5
CH3COCl, (CH3CO)2O
C6H5COCl + NaOH
HCl, HBr, HI
H2, Ni catalyst C6H11OH
HNO3 (aq) O2NC6H4OH formed
HOC6H4SO3H
HOC6H2Br3
I2, OH (aq)
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[H+]
CH3COOH (aq) ⥨ H+ (aq) + CH3COO- (aq)
- +
a
Work Example
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Reactions of carbonyl compounds
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Manufacture of Paracetamol
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• refer to chromium, copper and vanadium chemistry from notes.
Reaction of Fe2+ (aq) with MnO4- (aq)
The first reaction transfer 1 electron, but the second transfers 5 electrons.
Multiply the first by 5:
5Fe2+ (aq) → 5Fe3+ (aq) + 5e-
MnO4- (aq) + 8H+ (aq) + 5e- → Mn2+ (aq) + 4H2O (l)
Then add the equations, cancelling out the electrons:
MnO4- (aq) + 8H+ (aq) + 5Fe2+ (aq) → Mn2+ (aq) + 4H2O (l) + 5Fe3+ (aq)
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Nitration
This reaction happens best at around 50oC to form nitrobenzene, C 6H5NO2. The
electrophile is the nitronium ion, NO2+, formed from a mixture of concentrated nitric (v) and
sulphuric acids:
HNO3 + H2SO4 → NO2+ + HSO4 + H2O
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Nitration of Benzene
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NO2 NH2
+ 3H2 + 2H2O
Sn + 2HCl Sn2+ + 2Cl- + H2 (g)
Oxidation of alcohols
Oxidation of primary alcohols gives aldehydes, provided that conditions are controlled to avoid
further oxidation to a carboxylic acid. Oxidation of secondary alcohols gives ketones. Acidified
sodium dichromate (VI) is often employed for oxidation in the laboratory. The oxidizing agent is
added slowly to the alcohol. The temperature is kept below the boiling.
A laboratory method of
preparation is the
oxidation of alcohols to
aldehydes and ketones...
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Preparation of bromoethane from ethanol
Acylation
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Heating under Reflux
Organic reactions usually involve the breaking of covalent bonds - a slow process often requiring
prolonged heating. Refluxing allows organic mixtures to boil for a long time any escaping vapours
are condensed and returned to the reaction flask. As most organic substances are flammable, it is
safer to heat the mixture using an electric heater or a water both reaction than a Bunsen burner.
• A round- bottomed flask.
• A reflex condenser with the water entering at the bottom and leaving at the top.
• the top of the reflux condenser being open.
• the flask being heated using an electric heater or water or oil both or a sound tray.
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Recrystallization
Recrystallization is the method used to purity solids. A solvent has to be formed in which the
substance is soluble when the solvent is hot, but insoluble (or very muchless soluble) when it is
cold.
• Dissolve the impure solid in the minimum of hot solvent.
• Remove any undissolved impurities by filtering the hot solution through a fluted filter paper
in to a conical flask. A Buchner funnel could be used for rapid filtration.
• Allow the solution to cool.
• Filter the mixture of the pure solid and the solvent under reduced pressure, using a Buchner
funnel collect the solid on the filter paper and dischard the liquid, which will contain the
impurities in solution.
• Wash the solid on the filter paper with a little ice-cold solvent and leave the solid to dry.
Melting point of the solid is matched with date with data book value.
Benzoic acid is very soluble in hot water, but almost insoluble in cold water therefor, it can be
purified by recrystallization from hot water.
Derivates aldhyde and ketone can be obtained by recrystallization from hot ethanol.
Recrystallization
Washing: Unwanted impurities can often be removed by shaking the reaction products with
water or with sodium carbonate solution. Carbonates react with excess acid present, releasing
CO2. When the effervesce causes the acid has been removed.
Drying: Organic products often contain traces of water from the aqueous reagents used liquids
continue dried by being left in solvent with a drying agent such as silica gel or anhydrous CaCl 2.
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Simple Distillation:
Most organic reactions do not go to completion and there are often side reactions. This means
that the desired product is present in a mixture. Organic substances are volatile, so they can be
separated from non-volatile in organic species such as acid, alkali , salts by distillation.
If there is a large enough difference in the boiling temperatures of organic substances present in
a mixture, then distillation can be used to separate them.
• A round bottomed or pear-shaped flask containing the mix.
• A thermometer, the bulb of which must be positioned level with the outlet.
• A condenser with the water going in at the bottom and leaving at the top.
• An open receiving vessel, such as a beaker.
• The flask being heated using an electric heater.
Safety issues
• Distillation and heating under reflux must be carried out in a fume cupboard if the vapour of
one of the reactants or products is harmful, poisonous (toxic) or irritant.
• If a mixture is being heated under reflux or distilled, there must be some outlet to the air. If
there is not pressure will build up in the apparatus which will then fly apart, spraying hot
flammable and often corrosive liquid around.
• Gloves must be worn when corrosive substance are used harmful chemicals can be absorbed
through the skin.
• the flask should never be heated with a raked Bunsen flame. This because almost all organic
substances are flammable.
• Safety glasses and laboratory coats are worn at all times.
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Steam distillation
Steam distillation is used to extract a volatile liquid which is immiscible with water, from a
complex mixture. It is particularly useful for obtaining a substance that would decompose at its
boiling point the liquid boils below the boiling temperature of water so no decomposition of the
product takes place.
Steam distillation is used to extract phenyl amine from the reaction mixture often the reduction
of from the reaction mixture often the reduction of nitrobenzene with tin and concentrated HCl.
Procedure:
• Steam distil and collect the distillate until pure water distils over.
• Pour the mixture into a separating funnel and run off the aqueous layer.
• Add lamps of anhydroes potassium carbonate to the organic layer and leave.
Fractional distillation
Fractional distillation can be used to :
• Purify a liquid
• Separate a mixture of two liquids.
The impure liquid or mixture of liquids is placed in a round bottomed flask and a fractionating
column is fitted. The thermometer is positioned so that its, bulb is opposite the side arm and a
condenser is fitted to the side are. The apparatus must be open either at the top of the adapter
or when the distillate drips into the flask. The liquid with the lower boiling temperature distils
even first.
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Solvent extraction:
Many Organic materials have different solubilities in different solvents. When tow solvents are
immiscible, the products can be concentrated in one layer and the remaining reactants in the
ofter. The layers are then separated using a separating funnel. Solvent extraction is used in the
preparation of aromatic amine from nitro benzene.
Example: Iodine is soluble in both hexane and in aqueous potassium iodide solution. Hexane and
water do not mix they are immiscible. The iodine solute distributes itself between the two
solvents
I2 (aq) ⥨ I2 (hexane)
Solvents A
Solute is
distributed between
immiscible solvents
Solvents B
[𝒔𝒐𝒍𝒖𝒕𝒆 𝒊𝒏 𝒔𝒐𝒍𝒗𝒆𝒏𝒕 𝑨]
Partition coefficient = [𝒔𝒐𝒍𝒖𝒕𝒆 𝒊𝒏 𝒔𝒐𝒍𝒗𝒆𝒏𝒕 𝑩]
[𝑰𝒐𝒅𝒊𝒏𝒆 𝒊𝒏 𝒔𝒐𝒍𝒗𝒆𝒏𝒕 𝑨]
Partition coefficient = [𝑰𝒐𝒅𝒊𝒏𝒆 𝒊𝒏 𝒔𝒐𝒍𝒗𝒆𝒏𝒕 𝑩]
Large partition coefficient ≥ 1 indicates that iodine is much more soluble in solvent A than in
solvent B.
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Determination of boiling and melting temp:
Pure liquids boil within a range of 1 - 2oC pure solids melt within a range of 1oC the boiling
temperature of a liquid varies with the external pressure but the melting temperature of a solid
does not change significantly.
Method of deterring melting point
• Insert same of the pure solid into a capillary tube and then attach the tube open and upwards
to a thermometer with a rubber bond.
• Place the thermometer into a bath of liquid the liquid must boil at a higher temperature them
the melting point of the solid being tested.
• Slowly heat the liquid bath, with constant stirring and observe the solid in the capillary tube.
Not the temperature what the solid melts.
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