Shawon Notes Chem A Levels

GCE
Chemistry
User guide
Edexcel Advanced Subsidiary GCE in Chemistry (8CH01)
Edexcel Advanced GCE in Chemistry (9CH01)

Internal Assessment of Practical Skills
Issue 2
May 2008
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This specification is Issue 2. Key changes are sidelined. We will inform centres of any
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Prepared by Sarah Harrison
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© Edexcel Limited 2008
Contents
Introduction 1
1 — The scheme of assessment 3
1.1 Activities 3
1.2 Conditions under which assessments are to be carried out 3
1.3 Materials allowed when carrying out assessment activities 4
1.4 Health and safety 4
2 — Activity b: Qualitative observation 5

2.1 Recording observations 5
2.2 Making inferences from observations 6
3 — Activity c: Quantitative measurement 7

3.1 Accuracy 7
3.2 Errors 8
3.3 Calculations 8
3.4 Graphs 9
3.5 Assumed laboratory skills 9
4 — Activity d: Preparation 11
5 — Activity c+d: Multi-stage experiment 12
Reference section 13
A — Inorganic compounds and elements 13
1 Appearance 13
2 Flame tests 14
3 Heating 14
4 Recognition and identification of common gases 15
5 Action of dilute acids 15
6 Tests for oxidizing and reducing agents 16
7 Hydrogen peroxide solution 16
B — Precipitates 17
1 Sodium hydroxide solution 17
2 Ammonia solution 18
3 Barium chloride solution 18
4 Silver nitrate solution 19
5 Concentrated sulfuric acid 19
C — Organic compounds 20
1 Appearance 20
2 Solubility 20
3 Ignition 20
4 Chemical tests 21
D — Spectroscopy 23
1 Mass spectrometry 23
2 Infrared spectroscopy 23
3 Nuclear magnetic resonance (nmr) 23
Introduction
This User guide has been written for students to help them in preparing for the tasks that are
part of the internal assessment of practical skills. Teachers may also find this information
helpful when preparing students for the assessment activities. The material contained in the
booklet does not extend the specification content, but aims to help students to succeed in the
assessment activities by:
• explaining in more depth what is required in carrying out the activities, making
observations and measurements with appropriate precision and recording these
methodically
• advising them how to interpret, explain, evaluate and communicate the results of the
activities clearly and logically using the relevant chemical knowledge, understanding and
appropriate specialist vocabulary.
User guide (Internal Assessment of Practical Skills) — Edexcel AS/A GCE in Chemistry (8CH01/9CH01) 1
— Issue 2 — May 2008 © Edexcel Limited 2008
2 User guide (Internal Assessment of Practical Skills) — Edexcel AS/A GCE in Chemistry (8CH01/9CH01)
1 — The scheme of assessment
1.1 Activities
At both AS and A2 Level the skills being assessed in the activities are:
a General practical competence (GPC) (verification)
b Qualitative observation (14 marks)
c Quantitative measurement (14 marks)
d Preparation (12 marks)
The maximum mark available at both AS and A2 Level is 40.
Students will have their practical skills assessed by carrying out the assessment activities on a
number of occasions throughout the course. The assessment activities are set by Edexcel.
For activity a, the teacher is required to confirm that students have completed a range of
practicals over the whole year and developed their laboratory skills. Students must have
carried out at least five practicals in class. The practicals that the students complete must
cover the three areas of physical, organic and inorganic chemistry. These five practicals can
be either core practicals, or suitable alternatives.
The marks for activities b, c and d are awarded following the teacher’s application of the
mark schemes that accompany each assessed activity. Students need only carry out one
exercise for each of activities b, c and d. However they may carry out more than one. In this
case, only the highest mark for each activity will count towards the final mark out of 50.
At A2 there is the option of completing a multi-stage experiment at A2, which consists of
activities c and d together in a longer practical, which is worth 26 marks.
Teachers have the option of marking these activities or having them marked by Edexcel.
1.2 Conditions under which assessments are to be carried out
The practical assessment activities must be carried out under controlled conditions that
guarantee that students produce individual work. This includes those activities that involve
the processing of results. Students must not consult with each other during the activities.
Some activities can be completed in a laboratory session of approximately one hour. When an
activity has to be carried over to a following session students must not remove any materials,
including results and instruction sheets, from the laboratory. Instead, these must be collected
by the teacher and reissued at the beginning of the next session when the activity is to be
completed.
1.3 Materials allowed when carrying out assessment activities
Each activity has a cover sheet and a student brief giving full instructions for carrying out the
activity and the questions based on it.
During the activity students must not refer to books and notes although the data booklet is
required for some exercises. This User guide must not be used as a reference when carrying
out the internal assessment tasks.
1.4 Health and safety
Students must follow the health and safety rules which normally operate in their chemistry
laboratories, including the following:
• eye protection must always be worn
• laboratory coats must be worn when appropriate
• plastic gloves must be worn when supplied for a particular exercise
• all substances should be regarded as being potentially toxic and hazardous
• HazChem labels (eg flammable) should be read and appropriate precautions (eg keep
liquid away from flame) taken
• all substances spilled on the skin should be rinsed off immediately
• chemicals must never be tasted
• gases and vapours should never be smelt unless the question instructs the students to do
so, and then this should be done only with great care.
2 — Activity b: Qualitative observation
Activity b will be assessed by tasks that include a number of tests to be carried out, usually on
a test tube scale. The instructions for each test will include details on quantities to be used,
whether heat is required and whether excess reagent should be added. The reagents used for
the tests will be limited to those included in the specification. Similarly, unknowns will be
limited to compounds containing the ions, elements and organic compounds with the
functional groups listed in the specification. As part of a task to identify an organic unknown,
spectroscopic data may be included for students to analyse. Other physical data such as
melting temperatures may also be given.
These qualitative observation tasks will change each year.
2.1 Recording observations
After a student has carried out each test, as instructed in the task, they must communicate
the results by giving a brief description of what has been observed. Possible changes that can
occur during tests are listed below, along with examples of what students should write in the
observation boxes.
Possible change Example of observation

a colour change in solution yellow solution turns orange
the formation of a precipitate white precipitate (ppte is allowed) is formed
a precipitate dissolves in excess precipitate dissolves in excess to form a green
reagent solution
a gas is evolved bubbles of gas or effervescence
tests on a gas the gas turned damp red litmus paper blue
flame tests yellow flame
a solid dissolves dissolves to give a blue solution
a reaction is exothermic the mixture becomes hot
a reaction is endothermic the mixture feels cold
a coloured solution loses its colour the yellow solution turns colourless
There are a number of common mistakes which students make when recording their
observations. The following should be avoided.
• Referring to ‘layers’ in test tubes. Almost certainly the presence of layers is due to
inadequate mixing of the reagents. The exception to this is when an organic liquid is mixed
with an aqueous solution, or with water, in which case ‘layers’ may be a valid observation.
• Describing colours with elaborate adjectives such as brown-black or blue-green. Marks are
awarded for simple descriptions of the colours of solutions and precipitates, such as black
or blue, even if there is a trace of a second colour.
• Stating that a gas is evolved without making an observation such as bubbles or
effervescence.
• Using clear instead of colourless for a solution. All solutions are clear even if coloured, eg
copper sulfate solution is clear but coloured blue, whereas sodium sulfate solution is
colourless.
2.2 Making inferences from observations
The purpose of asking students to make inferences from their observations is to test their
knowledge, understanding and evaluation of the chemistry which leads to the observations.
Activities include asking students to identify precipitates or gases formed in a test and which
are recorded as an observation. Also, students could be asked to identify the unknown
compound following a series of tests.
In some cases the test may be enough to enable students to suggest the identity of a
particular ion or functional group, but in others a number of possibilities may exist as a result
of a single test.
Example 1
The addition of aqueous ammonia to an inorganic compound produces a green precipitate. The
inference from this test alone should be iron(II) hydroxide, chromium(III) hydroxide or
nickel(II) hydroxide.
Example 2
In an organic analysis, a compound produces an orange precipitate with
2,4−dinitrophenylhydrazine. The expected inference would be that the unknown compound is
an aldehyde, ketone or carbonyl compound. If a following test shows that the compound is an
aldehyde then the inference still stands, as this was valid on the basis of the
2,4−dinitrophenylhydrazine test. If more is known about the compound, for example its
molecular formula and the fact that it cannot be oxidised, then it may be that the compound
can be identified as a result of the 2,4−dinitrophenylhydrazine test.
3 — Activity c: Quantitative measurement
Activity c will be assessed through tasks that involve using apparatus to make measurements
and to process the results, to draw conclusions and evaluate the procedure.
Quantitative activities could involve:
• a volumetric analysis task
• a simple thermochemistry task
• a task to follow the rate of a reaction.
3.1 Accuracy
Unless an activity instructs students differently, they should assume that readings from
equipment and apparatus should be made with the following precision.
Apparatus Precision of reading

pipette one volume only of 25.0 cm3
burette each volume to the nearest 0.05 cm3
mean titre to 0.05 cm3 or to the second decimal place
measuring cylinder a 100 cm3 size to 5 cm3, a 10 cm3 size to 1 cm3
balance readings should be made to 0.01 g or 0.001 g depending on the
precision of the balance
timers normally read to the nearest second.
thermometers 0 to 100°C thermometers should be read to the nearest 1.0°C
0 to 50°C thermometers to an accuracy of at least 0.5°C
The following points are important.

• When students record readings they should include the appropriate number of decimal
places. For example a burette reading of exactly 24.7 cm3 should be recorded in a results
table as 24.70 cm3.
• When titres have to be averaged, the mean should be expressed to either the nearest
0.05 cm3 or to the second decimal place. Eg if a student records four titres as listed below
the mean should be calculated as:
26.50 + 26.25 + 26.60 + 26.65

= 26.5 cm3
4
• If the student decides to ignore the second titre and to average the remaining three:
26.50 + 26.60 + 26.65

= 26.583
3
which should be recorded as 26.60 cm3 or as 26.58 (to the second decimal place).
• Students should try to obtain at least two titres within 0.20 cm3, or better, of each other
and average these to obtain a mean titre. Students should make it clear which titres have
been used to obtain a mean.
• A final result should only be given to the same number of significant figures as is suggested
in the exercise. For example a task to find a ΔH value may involve a weighing of 1.56 g and
a temperature rise of 7.5°C. A student who calculates a value of ΔH from these figures
may obtain a value of 195.6843 on a calculator but this should be finally recorded as 200
kJ mol−1, although 196 kJ mol−1 may also be acceptable.
• Units should always be included with a quantitative result.
A significant proportion of the marks awarded for a quantitative measurement activity will be
for accuracy. These marks will be awarded by comparing the student’s results with an
expected value.
3.2 Errors
Students should appreciate that any piece of equipment (burette, pipette, thermometer,
balance) used in a quantitative exercise has an uncertainty associated with its use. Even if the
equipment is used carefully, the uncertainty leads to an error in the reading and in the final
result.
Eg a balance has an uncertainty of 0.01 g when read to the second decimal place. A reading of
2.64 g recorded in an experiment has an error of:
0.01
× 100% = 0.38%
2.64
The following points will apply.
the uncertainty in the equipment

1 The error in the reading = × 100%
the reading
2 Students should:
• calculate the error involved in using a particular piece of equipment and state what effect
this has on the overall accuracy of the activity
• understand that the percentage error would be affected by the magnitude of the quantity
being measured. There will be a greater error in weighing a mass of 2.64 g than in
weighing 8.64 g using the same balance.
3 Only a simple treatment of errors is needed and students will not be asked to combine
errors.
3.3 Calculations
Usually calculations will be structured. Students will be taken/guided through a series of steps
leading to a final answer. Since most of the marks for these steps will be for use of a correct
method, rather than for the numerical answer, it is important that students include their
workings even if these seem to be trivial. Marks cannot be awarded for an incorrect answer
without workings, but a correct method followed by an incorrect answer can often receive
credit. Units, if appropriate, should always be included with a quantitative result.
3.4 Graphs
For some activities students will need to treat their readings graphically.
The following are some useful points for students to consider when drawing graphs.
• Put the dependent variable, the quantity being measured (eg temperature), on the y−axis.
And the pre-determined quantity (eg volume of solution) on the x−axis.
• Choose the scales so that the results are spread out as far apart as the size of the grid
allows, but this should not be at the expense of using a sensible scale, eg using 1 cm on
the axis to represent 3 or 4 units might spread the readings better than using 1 cm to
represent 5 units, but the scale would be hard to read.
• The origin (0,0) does not need to be included on either scale if it is not relevant,
• For example if temperature readings between 21.0°C and 39.0°C are to be plotted there is
no need to begin the y−axis at 0. Rather it could be scaled from 20.0°C to 40.0°C.
• Clearly label the axes with the quantity being plotted (eg time) and its units
(eg minutes).
• Join the points plotted with a continuous straight line or smooth curve. Since the readings
are all subject to experimental error the line drawn may not necessarily pass through
every point. Points should never be joined by a series of short, straight lines.
3.5 Assumed laboratory skills
The instructions for carrying out a quantitative measurement activity will include the essential
points for the particular task. For example:
• which chemicals to use
• the quantities needed
• the sequence of steps in the method
• the readings to be taken.
The assessment activities will assume that students have developed a range of routine
practical skills in their course leading up to the exercise. Instructions may not, therefore,
include every step needed to gain accurate readings.
Examples of normal laboratory procedures which may not be referred to in the instructions
include:
• burettes, pipettes and measuring cylinders should be rinsed with the solution they are to
contain
• a pipette filler should always be used with a pipette
• conical flasks and volumetric flasks should be rinsed out with distilled water
• a burette should be read at eye level
• a thermometer bulb must be held in the centre of a solution when temperature readings
are taken
• care should be taken not to lose drops of a solution when thermometers or stirring rods are
removed from it
• containers may need to be labelled if this has not already been done
• care should be taken as to where apparatus is placed on the bench, eg temperature
measurements should not be taken in apparatus standing next to a Bunsen burner, in a
patch of sunlight or in a strong draught.
4 — Activity d: Preparation
Activity d is assessed through tasks in which students follow a procedure to prepare and, in
some cases, purify an inorganic or organic compound. Marks are awarded for the student's
ability to follow laboratory procedures and to use apparatus competently and safely.
Preparations can include some of the following laboratory procedures:
• distillation
• heating under reflux
• filtration, including under reduced pressure
• purification by washing in a separating funnel
• solvent extraction
• drying
• boiling and melting temperature determination
• crystallization and recrystallization.
Following some preparations students will be asked to calculate the maximum mass of product
and a percentage yield.
5 — Activity c+d: Multi-stage experiment
Instead of completing activities c and d separately, students could complete a multi-stage

experiment, which combines the two. This would be a longer practical which covers all of the
same aspects of c and d mentioned above. This would most likely be completed in two
laboratory sessions and students would have to hand in their notes and results at the end on
one session, and receive these back when they complete the practical in the second session.
Reference section
A — Inorganic compounds and elements
1 Appearance
• Coloured crystalline substances are usually hydrated salts of transition metals.

The colour of the solid substance may provide evidence for its identity.
Colour Possible transition metal ions in salt

blue copper(II)
pale green iron(II)
green copper(II), chromium(III), nickel(II)
purple manganate(VII)
brown iron(III)
pink manganese(II)
yellow chromate(VI)
orange dichromate(VI)
• The colours of transition metal ions in dilute, aqueous solution are shown in the table
below.
Colour Possible identity

blue copper(II)
green iron(II), chromium(III), nickel(II)
brown / yellow iron(III)
pale pink manganese(II)
yellow chromate(VI)
orange dichromate(VI)
purple manganate(VII)
colourless zinc(II)
2 Flame tests
• To carry out a flame test, a clean nichrome wire is used to mix a sample of a solid with
one drop of concentrated hydrochloric acid. The wire is held in progressively hotter
parts of a non-luminous Bunsen flame.
Flame colour Inference

yellow sodium ion
lilac potassium ion
yellow-red* calcium ion
red* lithium or strontium ion
pale green barium ion
* Further tests would be needed to distinguish these ions.
3 Heating
• Gases or vapours may be evolved on heating a solid compound.
Gas or vapour Possible source

carbon dioxide carbonates of metals other than group 1
oxygen group 1 nitrates (other than Li)
oxygen and nitrogen nitrates (other than Na or K)
dioxide
water hydrated salts
4 Recognition and identification of common gases
Gas Observations
oxygen colourless gas which relights a glowing splint
carbon dioxide colourless gas which gives a white precipitate with
limewater (calcium hydroxide solution)
ammonia colourless gas which turns moist red litmus paper blue and
forms white smoke with hydrogen chloride
nitrogen dioxide brown gas*
hydrogen colourless gas which ignites with a ‘pop’
hydrogen chloride steamy fumes on exposure to moist air, acidic and forms
white smoke with ammonia
chlorine pale green gas which bleaches moist litmus paper
bromine brown gas*
iodine purple vapour
water vapour turns blue cobalt chloride paper pink
* Bromine dissolves in organic solvents to form a brown solution whereas nitrogen

dioxide is insoluble.
5 Action of dilute acids
• When dilute sulfuric or hydrochloric acid is added to a substance a gas may be evolved
or there may be a colour change in the solution.
Action of acid Possible source

carbon dioxide evolved carbonate
hydrogen evolved a metal
yellow solution turns orange chromate(VI) to dichromate(VI)
sulfur dioxide evolved and pale yellow thiosulfate
precipitate formed
6 Tests for oxidizing and reducing agents
Reducing agents usually:

decolourise aqueous acidified potassium manganate(VII) and
may also turn aqueous, acidified potassium dichromate(VI) from orange to green.
Reducing agents include:
iron(II) ions
iodide ions
hydrogen peroxide.
Oxidizing agents usually:

liberate iodine as a brown solution or black solid from aqueous potassium iodide.
Iodine solution gives a blue-black coloration with starch.
Oxidizing agents include:
acidified manganate(VII) ions
acidified dichromate(VI) ions
hydrogen peroxide
copper(II)ions
aqueous chlorine
aqueous bromine.
7 Hydrogen peroxide solution
Aqueous hydrogen peroxide (H2O2) can act as both an oxidizing and a reducing agent often
with the evolution of oxygen, although this may be unreliable.
Observation on adding H2O2 Inference

brown precipitate manganate(VII), brown precipitate is
MnO2
purple solution is decolourised manganate(VII) in acid solution
pale green solution turns yellow iron(II) to iron(III) in acid solution
green precipitate turns brown iron(II) hydroxide to iron(III) hydroxide
green alkaline solution goes yellow chromium(III) to chromate(VI)
brown solution or black precipitate iodine from iodide in acid solution
B — Precipitates
When two aqueous solutions are mixed together and an insoluble compound is formed this is
known as a precipitate not a suspension. The observation that a precipitate is formed should
always be accompanied by the colour of the precipitate, even if this is white. Some reagents
should be added until they are in excess. This may result in a precipitate forming then
dissolving in excess reagent.
1 Sodium hydroxide solution
• When dilute sodium hydroxide (NaOH) solution is added to a solution containing a

metal ion a precipitate of the insoluble hydroxide, eg Mn(OH)2, is usually formed.
Precipitates which are amphoteric hydroxides will dissolve in excess sodium hydroxide
to give a solution containing a complex ion, eg [Cr(OH)6]3−.
• Students should assume that aqueous sodium hydroxide should be added until it is in
excess even if this is not explicitly stated in the instructions.
Observation on adding dilute Observation on adding Likely ion

NaOH excess dilute NaOH
green precipitate precipitate dissolves to a chromium(III)
green solution
off-white precipitate which precipitate is insoluble manganese(II)
darkens on exposure to air
green precipitate which turns precipitate is insoluble iron(II)
brown on exposure to air
brown precipitate precipitate is insoluble iron(III)
green precipitate precipitate is insoluble nickel(II)
blue precipitate precipitate is insoluble copper(II)
white precipitate precipitate dissolves to a zinc(II)

colourless solution
white precipitate precipitate is insoluble magnesium, barium,
strontium, calcium
no precipitate sodium, potassium
no precipitate but ammonia ammonium

evolved on warming
2 Ammonia solution
• Dilute aqueous ammonia (NH3), when added to a solution containing a cation, will form
the same hydroxide precipitate as dilute sodium hydroxide solution, eg Mn(OH)2. Excess
aqueous ammonia may dissolve the precipitate to form a complex ion, eg
[Cu(NH3)4(H2O)2]2+.
• Students should assume that aqueous ammonia must be added until it is in excess.
Observation on adding dilute Observation on adding excess Likely ion

aqueous NH3 dilute aqueous NH3
green precipitate precipitate is soluble to give chromium(III)
green solution
off-white precipitate precipitate is insoluble manganese(II)
green precipitate turning precipitate insoluble iron(II)
brown
brown precipitate precipitate insoluble iron(III)
green precipitate precipitate dissolves to give nickel(II)
blue solution
blue precipitate precipitate dissolves to give copper(II)
deep blue solution
white precipitate precipitate dissolves to give zinc(II)
colourless solution
white precipitate precipitate is insoluble magnesium
3 Barium chloride solution
• Aqueous barium chloride forms precipitates of insoluble barium salts with a number of
anions but is usually used as the test for the sulfate, SO42−, ion. Aqueous barium
chloride is usually used with dilute hydrochloric acid.
Anion Precipitate Addition of dilute HCl

colour formula
sulfate white BaSO4 precipitate is insoluble
sulfite white BaSO3 precipitate dissolves
carbonate white BaCO3 precipitate dissolves with effervescence
If dilute hydrochloric acid is added to the anion solution before aqueous barium chloride
then only the sulfate will form as a precipitate.
4 Silver nitrate solution
• Aqueous silver nitrate is commonly used to test for the presence of halide ions in
solution. Anions which would interfere with the test (eg carbonate) are removed by
adding dilute nitric acid before the aqueous silver nitrate.
• The identity of a halide may be confirmed by the addition of aqueous ammonia, (NH3),
both dilute and concentrated.
• Silver halides which dissolve in ammonia do so to form a colourless solution of the
complex ion, [Ag(NH3)2]+.
Anion Precipitate Addition of aqueous NH3

colour formula dilute concentrated
chloride white AgCl soluble
bromide cream AgBr soluble in excess soluble
iodide yellow AgI insoluble insoluble
5 Concentrated sulfuric acid
• When a few drops of concentrated sulfuric acid (H2SO4) are added to a solid halide the
observed reaction products may be used to identify the particular halide ion present.
This is a potentially hazardous reaction.
• It must be carried out on a small scale and in a fume cupboard.
• The products in brackets will not be observed since they are colourless gases. The
halide ion may be identified without the need to test for these gases. No attempt
should ever be made to detect these gases by smell.
Halide Observations on adding Observed reaction

concentrated H2SO4 products
chloride steamy fumes, vigorous reaction HCl
bromide steamy fumes, brown vapour, HBr, Br2 (SO2)

vigorous reaction
iodide steamy fumes, black solid, purple HI, I2, S, (H2S)
vapour, yellow solid, vigorous
reaction
C — Organic compounds
Students will always be told if a compound, or mixture of compounds, to be identified is

organic. Often the molecular formula, or the number of carbon atoms in a molecule, of a
compound will be given. Chemical tests may be followed by spectroscopic information.
1 Appearance
Simple organic compounds are usually colourless liquids or white solids. It is unlikely that
appearance alone will provide firm evidence for identification.
2 Solubility
Solubility of compound Possible identity pH of Possible

solution identity
dissolve in water simple alcohols, simple above 7 amines
carboxylic acids,
propanone, simple
aldehydes, simple below 7 carboxylic
amines and their salts acids,
phenols
dissolve in dilute acid amines
but may not dissolve in
water
dissolve in aqueous carboxylic acids, phenols
alkali but may not
dissolve in water
3 Ignition
Igniting an organic unknown on a crucible lid may help in identifying it.
Observation Possible inferences

burns with a smoky flame aromatic, unsaturated eg alkene
burns with a clean flame saturated low molar mass compound
no residue most lower molar mass compounds
4 Chemical tests
The details of how these tests are to be carried out will be included in the instructions to
students in the assessment activities.
Test Observation Inference

warm with acidified potassium orange to green primary or secondary
dichromate(VI) solution alcohol, aldehyde
yellow solution is alkene
decolorised
shake with bromine water
if white phenol
precipitate also
formed
warm with aqueous precipitate: halogenoalkanes:
sodium/potassium hydroxide, acidify
white C−Cl
with dilute nitric acid then add
aqueous silver nitrate cream C−Br
yellow C−I
phosphorus(V) chloride steamy fumes of OH group in alcohols

HCl that turn damp and carboxylic acids
blue litmus paper
red
2,4−dinitrophenylhydrazine solution orange precipitate C=O group in

aldehydes and
ketones
boil with Fehling’s or Benedict’s blue solution gives aldehyde

solution red precipitate
warm with ammoniacal silver nitrate silver mirror aldehyde

(Tollens’ reagent)
sodium or potassium carbonate or effervescence carboxylic acid

hydrogencarbonate solution
add a small piece of sodium effervescence alcohol, phenol or

(bubbles), sodium carboxylic acid
dissolves, white
solid formed
warm with carboxylic acid and a few ester smell, eg alcohol
drops of concentrated sulfuric acid glue-like
Test Observation Inference
sodium nitrite and dilute hydrochloric orange precipitate aromatic amine
acid followed by an alkaline solution
of phenol in ice-cold conditions
iodine in alkaline solution pale yellow methyl ketone or

precipitate ethanal,
C CH3
O
methyl secondary
alcohol or ethanol
CH CH3
OH
D — Spectroscopy
Modern instrumentation plays a vital role in the characterisation and identification of

molecules and ions. The sections which follow will enable interpretation of the data likely to
be presented to students.
1 Mass spectrometry
Simplified mass spectra will be given which may be interpreted in two main ways.
1 The value of the compound’s relative molar mass may be obtained from the m/e value of
M+, the molecular ion. This will have the highest value of m/e. This need not necessarily
be the ‘base’ peak, which is simply the most abundant ion. Questions will be set in such a
way that students will not be confused by the presence of a line due to the (M + 1) ion.
2 The fragmentation pattern of the spectrum gives useful information about the structure of
the molecule. For example, a peak at m/e 29 is likely to be due to the presence of a C2H5
group in the molecule. Students are reminded that, when asked, they should give
displayed structures for fragments, which must carry a positive charge also.
2 Infrared spectroscopy
This is a very powerful non-destructive technique which provides information regarding the
nature of covalent bonds within the molecule.
Students should look at the most intense absorptions to quickly gain structural clues. Table 1
provides sufficient details to enable the principal bands to be assigned. Students should
remember that absorption frequency is affected by the chemical environment and that
absorption may take place outside the range given.
The connection between structures should be recognised. For instance, an alcohol [O-H]
stretch will be accompanied by a [C-O] stretch.
Please see the Data booklet for specific IR spectroscopy data.
3 Nuclear magnetic resonance (nmr)
Nuclear magnetic resonance spectra may be included as part of an investigation into

structure. Spectra will be high resolution with possible spin–spin coupling displayed.
Please see the Data booklet for specific nmr data.
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May 2008
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Chem Factsheet
January 2003 Number 48
Laboratory Chemistry - Organic Techniques

Before working through this Factsheet you should: 2. Distillation
• Have some practical experience in organic chemistry; Distillation can be used to isolate a liquid product if the boiling point of the
• Undersatnd the Organic Chemistry covered so far at AS and A2 (covered product is significantly different to that of the rest of the reaction mixture.
in Factsheets 15, 16, 17, 27, 31, 32, 33, 34, 35 and 39);
• Understand the laboratory techniques for separating and purifying Distillation is used to purify a liquid by boiling it and then condensing it
(covered in Factsheet 30). away from its impurities.
After working through this Factsheet you will:

• Have met and revised common practical techniques in organic chemistry;
• Be able to represent the relevant equipment with simple diagrams; Thermometer
• Be able to assess simple organic practicals in terms of safety.
As several of these techniques were discussed in detail in Factsheet 30, this

Factsheet is designed to be more of a focused revision aid. Thermometer pocket
It is necessary for candidates to display a familiarity with a variety of

practical techniques in organic chemistry when preparing for both written
exams and practical exams or assessment. Liebig condenser
1. Heating under reflux

Reflux apparatus are necessary when a reactant has a low boiling point, or water
the reaction is slow at room temperature. The condenser prevents the out
escape of any of the volatile reagent or product. water in
Heat
Receiver
Distillate
condenser
to sink
3. Fractional Distillation
Fractional distillation is most commonly used to separate two liquids if the
boiling points are quite close. Pure samples of each liquid can usually be
obtained, unless the boiling points are too close.
Thermometer
from tap
Thermometer pocket
reaction mixture Liebig condenser
to vacuum pump
water for distillation
Fractionating out
column water in under reduced
pressure
heat
Distillate
Distillation flask
Heat
1
Laboratory Chemistry - Organic Techniques Chem Factsheet
Candidates need to be familiar with the following types of graphs plotting 5. Recrystallisation
boiling points against composition. To purify the solid product.
A suitable solvent for recrystallisation will often be evident (e.g. the solvent
Chemical A must be separated from chemical B. Chemical A has a higher from which the crude product was initially crystallised), and should be a
boiling point than chemical B, so chemical B is a more volatile liquid. solvent which will not react with the solid. The solubility of the solid
should be high near the boiling point and low near room temperature.
Candidates should learn the method of recrystallisation.
Boiling
point A
• Dissolve the solid in the minimum volume of hot solvent.
T1 • Quickly filter the hot solution using preheated filter funnel and
T2 Boiling fluted filter paper.
point B • Collect the filtrate and allow to cool and the solid to recrystallise.
o
Temp. C • Use suction filtration (Buchner funnel) to collect the solid.
• Wash the solid with a small amount of cold solvent.
• Dry the solid product.
100% A composition 0% A 6. Melting Point Determination

0% B 100% B The melting point of a solid is used to judge the purity of the product. A
composition composition composition solid should have a sharp melting point, and recrystallisation should be
X Y Z repeated until this is obtained.
Consider a mixture of two chemicals A and B, of composition X. If it is Melting point should be determined using melting point apparatus.
heated it will boil at T1 oC to give a vapour of composition Y.
Note that Y is richer in the more volatile component than X. capillary tube thermometer
If Y is condensed and reboiled it will boil at a temperature T2oC, giving a
vapour of composition Z, where Z is richer in the more volatile component
B than Y was.
electrically
Eventually pure B will be distilled off from the top of the fractionating heated block
column and pure A will be left in the flask.
How the vapours are continuously condensed and reboiled will be discussed
in a later Factsheet, which will deal with the workings of fractional distillation
in even more detail.
illuminated
4. Filtration under reduced pressure cavity
To isolate a solid product from a liquid, suction filtration using a Buchner
(or Hirsch) Funnel is an effective method.
sample
Buchner funnel
and flask
The sample is placed in a capillary tube, and the temperature increased

slowly until it melts.
suction
Melting points can also be used for identification purposes.
7. Boiling point determination

Boiling points can also be used for identification purposes, and to check
the purity of a product. Boiling points are most commonly measured in the
process of distillation (see section 2).
A small amount of cold solvent should be used to wet the filter paper prior
to filtration, and to remove any solid remains from the reaction flask.
2
Laboratory Chemistry - Organic Techniques Chem Factsheet
8. Selecting an appropriate heat source

There are a variety of heat sources available in the laboratory, and heat is
often required for organic reactions to increase the rate of reaction or to
provide the activation energy to initiate the reaction.
Two things must be considered when selecting the type of heat source:
(a) The temperature or strength of heating required.
(b) Safety.
Consider the following options:

Bunsen burner
Direct, variable heat and accessible, but danger - do not use with flammable
reagents, solvents or products.
Electric heating mantle

No naked flame (so can be used with flammable chemicals), controllable
temperature, but a little cumbersome. Electricity, and necessary wiring,
obviously required.
Water bath
Useful when gentle heating required, as maximum temperature is that of
boiling water. Some water baths are electrically heated, whilst a simple
water bath is a beaker over a Bunsen flame, so candidates should be aware
if any flammable vapours may be produced.
organic chemial
water
heat
Oil bath
Same principle as water bath, but higher temperatures can be reached.
Take some time to reach required temperatures, and some time to cool
down again afterwards.
Exam Hint: - A note about safety during organic practicals.

Candidates should be able to make simple risk assessments
when it comes to practical work. A common type of exam question
will ask for safety precautions during a specified procedure. For
success in the exams and for your own personal safety, knowledge
of safe procedure is important.
It is assumed that students wear eye protection during practical

work, so the answer “wear goggles” will not suffice in response to
a question about safety.
Consider the following:
• Fume hoods should be used for all reactions involving toxic,
Acknowledgements:
irritant or carcinogenic chemicals.
• No naked flames should be used with flammable chemicals.
This Factsheet was researched and written by Kieron Heath
• The use of gloves is required when dealing with corrosive or Curriculum Press, Unit 305B, The Big Peg, 120 Vyse Street, Birmingham,
irritant chemicals such as concentrated acids. B18 6NF
ChemistryFactsheets may be copied free of charge by teaching staff or students,
provided that their school is a registered subscriber.
Use these ideas and common sense when answering questions about safety.
No part of these Factsheets may be reproduced, stored in a retrieval system, or
When carrying out practical procedures, be careful to follow the prescribed
transmitted, in any other form or by any other means, without the prior permission
method and pay attention to the risk assessment and safety notes.
of the publisher. ISSN 1351-5136
3
Chem Factsheet
January 2002 Number 30
Laboratory Chemistry - Separation &
Purification Techniques
After working through this Factsheet you will: This Factsheet mainly focuses on the practical techniques required once
• Have been introduced to a range of practical techniques; the initial reaction has been carried out, and the crude product has been
• Be able to give a short method describing each technique; formed in the reaction mixture.
• Understand how solid and liquid products can be isolated and
purified. These techniques are more general, as in most cases the crude product
must be:
Exam Hint: - Candidates should have a good knowledge of these
practical techniques, and be able to describe them concisely (with the
aid of diagrams if necessary). They are especially important when • Isolated - from the reaction mixture.
preparing for a practical exam or practical assessment of the “planning” • Purified - for use or identification.
skill, but may also be required in the written papers.
The practical techniques outlined in this Factsheet have been placed into
two groups - those associated with:
It is impossible to generalise about methods of preparation of crude chemical
products, as every compound is prepared in a slightly different manner.
1. isolation and purification of a solid product
Candidates should be aware, however, that examiners will ask about methods
2. isolation and purification of a liquid product.
of reactions covered elsewhere in the AS and A2 courses. Candidates
should be able to apply their existing knowledge to practical situations,
and will be given background information in the exam or assessment
question. 1. Isolation and Purification of a Solid Product
Once a solid product has been formed, the method, or plan, should commonly
One reaction condition worth mentioning here, however, is that of heating include three further steps:
under reflux, as it is very common in organic preparations (Fig 1).
a) Filtration
Reflux apparatus are necessary when a reactant has a low boiling point, or b) Recrystallisation
the reaction is slow at room temperature. The condenser prevents the c) Melting point determination.
escape of any volatile reagent or product.
a) Filtration
To isolate a crude solid product from a liquid, use suction filtration, using
Fig 1. Reflux apparatus a Buchner funnel (Fig 2).
Fig 2. Suction filtration
condenser
to sink
Buchner funnel
and flask
from tap suction
reaction mixture
heat A small amount of cold solvent should be used to wet the filter paper prior
to filtration, and to remove any solid remains from the reaction vessel - in
an effort to save as much of the solid product as possible.
1
Laboratory Chemistry - separation and purification Chem Factsheet
b) Recrystallisation - To purify the solid product 2. Isolation and Purification of a Liquid Product
A suitable solvent for recrystallisation will often be evident (e.g. the solvent There is slightly more to consider when planning how to extract a pure
from which the crude product was initially crystallised ), and should be a liquid product, as a liquid may be miscible or immiscible, acidic, or may
solvent which will not react with the solid. The solubility of the solid need drying.
should be high near the boiling point and low near room temperature.
Candidates should learn the method of recrystallisation. a) Separating Funnel - For use when separating immiscible liquids (Fig 4).
• Dissolve the solid in the minimum volume of hot solvent.

• Quickly filter the hot solution using preheated filter funnel and fluted
filter paper.
• Collect the filtrate and allow to cool and the solid to recrystallise.
• Use suction filtration (Buchner funnel) to collect the solid. solvent extraction or seperation
• Wash the solid with a small amount of cold solvent. of immiscible liquids
• Dry the solid product.
c) Melting Point Determination

The melting point of a solid is used to judge the purity of the product. A
solid should have a sharp melting point, and recrystallisation should be
repeated until this is obtained. Melting point should be determined using
melting point apparatus (Fig 3).
Fig 3. Melting point apparatus
capillary tube thermometer

If, after carrying out a reaction, candidates are left with a liquid product
which is immiscible with the rest of the reaction mixture, they must be able
to find out which layer (upper or lower) contains the product. This can be
electrically discovered by examining liquid density data - obviously the more dense
heated block liquid will be the lower layer.
The two layers, which meet at an interface, are physically separated by

running the lower layer out of the separating funnel (using the tap) and
retaining the upper layer in the funnel.
illuminated b) Neutralising Acidic Liquid Products

cavity Often acid conditions are required when preparing organic liquids, and the
acid should be neutralised by the addition of a solid base such as sodium
carbonate (Na2CO3), or sodium hydrogen carbonate (NaHCO3) solution.
The use of an indicator is not required as it is clear when the neutralisation

is complete as no further carbon dioxide gas is evolved on the addition of
the base.
sample
Care must be taken if sodium carbonate (or sodium hydrogen carbonate) is
added to a liquid and a stopper placed over the vessel so it can be shaken,
The sample is placed in a capillary tube, and the temperature increased as the pressure of the carbon dioxide gas formed must be periodically
slowly until it melts. released.
Melting points can also be used for identification purposes. Another by-product of the neutralisation reaction will be water, so an
aqueous layer may be formed. This can be removed using a separating
funnel and drying agent.
Example - Method for the preparation of Benzenecarboxylic acid.

Candidates would be given the background information in terms of the chemical reactions involved, and should be able to calculate reasonable quantities
of reactants. Focus here on steps 3, 4, 5 and 6 as they put the work covered so far in this Factsheet into a practical chemistry context.
(1) Add 40cm 3 of dilute sodium hydroxide solution to 1cm 3 of (4) Recrystallise the compound by dissolving the crystals in the minimum
ethylbenzenecarboxylate in a round-bottomed flask. Reflux for 30 amount of hot water and filtering the hot solution using preheated
minutes. filter funnel and fluted filter paper. Allow the filtrate to cool so that
crystals form.
(2) Transfer the mixture to a beaker and add dilute sulphuric acid until the
solution is just acidic. Use a glass rod and indicator paper to do this. (5) Use suction filtration to collect the crystals, wash with cold water
and let them dry.
(3) Use suction filtration (Buchner funnel and flask) to filter off crystals
of benzenecarboxylic acid. (6) When dry, weigh the solid product to calculate the yield, and determine
the melting point.
2
c) Drying of Liquid Products - the Removal of Water Fractional distillation will be discussed in more depth in future Factsheets.
The anhydrous solids calcium chloride or sodium sulphate can be added to
the liquid product if it is necessary to dry it. After addition and agitation, For either type of distillation, knowledge of the boiling point of the liquid
the mixture should be allowed to stand for a few minutes and then filtered. product is important.
The dry liquid can then be collected as the filtrate.
Distillation
Preparation of a halogenoalkane
Distillation can be used when the boiling point of the product is significantly
2-chloro-2-methylpropane can be prepared from 2-methylpropan-2-ol
different to that of the rest of the reaction mixture.
and hydrochloric acid. The reaction will take place at room temperature
Distillation is used to purify a liquid by boiling it and then condensing it as tertiary alcohols undergo substitution readily.
away from its impurities (Fig 5).
Boiling point of product (2-chloro-2-methylpropane) is 50 oC.
Fig 5. Distillation apparatus
CH3 CH3
H 3C C CH 3 + HCl → H 3 C C CH 3 + H 2 O
Thermometer
CH 3 Cl
2-chloro-2-methylpropane and 2-methyl-propan-2-ol are flammable, and
both volatile liquids at room temperature. Concentrated hydrochloric
Thermometer pocket
acid is very corrosive.
Given this background information, candidates should be able to suggest

a reasonable procedure plan, with safety precautions.
Liebig condeser
Procedure
1. Measure 10cm3 2-methylpropan-2-ol into a measuring cylinder.
water
out 2. Pour the 2-methylpropan-2-ol into a 50cm3 separating funnel, and
water in reweigh the measuring cylinder to calculate the exact mass of liquid
poured.
Heat
Receiver 3. Add 20cm3 concentrated hydrochloric acid (excess) a few cm3 at a
time, taking care to mix the reactants after each addition by inverting
the stoppered funnel. Ensure that any build up of gas pressure is
Distillate
released.
4. Leave the reaction mixture in a fume cupboard for 15 minutes, gently

Fractional Distillation agitating the mixture at intervals.
Fractional distillation is most commonly used to separate two liquids (if 5. Allow the 2 layers in the separating funnel to separate, then run off
the boiling points are fairly close). Pure samples of each liquid can usually and discard the lower aqueous layer.
be obtained, unless the boiling points are too close (Fig 6).
6. Add sodium hydrogen carbonate solution 2cm3 at a time to neutralise
Fig 6. Fractional distillation apparatus the remaining organic layer. Shake the funnel carefully, being sure to
release the build up of gas pressure. Continue the addition until the
excess acid is neutralised.
Thermometer
7. Allow layers to separate and discard the lower aqueous layer.
Thermometer pocket 8. Run the organic product into a small conical flask and add 3 spatulas
of anhydrous sodium sulphate to dry it. Stopper and swirl the flask
for 5 minutes.
Liebig condeser
9. Decant the liquid into a small pear-shaped flask.
to vacuum pump 10. Distil the product, collecting the fraction in the range 47 to 53 oC into
water for distillation
Fractionating a pre-weighed flask.
out under reduced
column water in
pressure 11. Find the mass of the purified product.
Safety Precautions
Distillate • Keep flammable liquids away from flames.
• Carry out acid addition in fume cupboard.
Distillation flask • Keep stoppers on bottles as much as possible.
• Wear gloves and safety spectacles.
Exam Hint: - Take note of the style of language used when writing
out a method - it needs to be clear, accurate and concise. Name
the apparatus, calculate quantities to be used, and use diagrams if
Heat appropriate.
3
Practice Question Answer

This is an example of a practical assessment task which. It is possible that (a) Conversion of 20 cm3 2-bromobutane to grams. (20 × 1.3 = 26g) 1
candidates would be given some general advice as to what areas to revise Conversion of grams 2-bromobutane to moles. (26/137 = 0.190) 1
and read about prior to the assessment, but notes and books would not be Recognise molar ratio 1:1, deducing moles of butan-2-ol. (0.190) 1
allowed whilst answering. Use 75% purity to calculate number of moles of butan-2-ol
required initially. (0.190/0.75 = 0.253 moles) 1
Planning the preparation of 2-bromobutane Deduce mass of butan-2-ol required initially (0.253 × 74 = 18.7g) 1
2-bromobutane is a liquid (density = 1.3gcm-3, Mr = 137) which is immisci- Converts grams to volume (cm3) of butan-2-ol required
ble with water. (18.7/0.8 = 23.4 cm3) 1
It is prepared from butan-2-ol (density = 0.8gcm-3, Mr = 74), by refluxing (b) Need for cooling / slow addition of conc. sulphuric acid. 1
it with solid sodium bromide, water and concentrated sulphuric acid. Reflux (for at least 30 minutes). 1
Diagram of reflux apparatus.
CH3CH2CHOHCH3 + Br − → CH3CH2CHBrCH3 + OH− (-1 for each error) 3
You are asked to plan a safe procedure for making 20 cm 3 of pure 2- Distillation 1
bromobutane, assuming a 75% yield. Made clear aim is to distil off upper organic layer. 1
Diagram of distillation apparatus. (-1 for each error) 3
Butan-2-ol dissolves in concentrated hydrochloric acid.
(c) Remove and discard upper aqueous layer. 1
The plan should include: Wash with concentrated hydrochloric acid to remove unreacted
butan-2-ol. 1
(a) The exact volume of butan-2-ol required (show your calculations). Collect lower layer. 1
(b) A description of the safe procedure of the preparation. Wash with an appropriate quantity of sodium hydrogen carbonate
Include: solution (2cm3 at a time) to remove excess acid. 1
• Diagrams of apparatus Remove stopper to ease pressure as gas is produced. 1
• Which layers are discarded and kept when immiscible liquids are Collect lower organic layer. 1
produced.
Dry using appropriate drying agent. 1
Filter or decant to remove desiccant. 1
(c) A description of all the steps in the purification process.
(d) Distil to further purify. 1
(d) A description of the final distillation of the pure product. Collection of distillate in temperature range (88-94 oC). 1
(N.B. there is no need to re-draw distillation apparatus).
(e) Identification of hazards 2
(e) All safety factors should be considered. e.g. corrosive nature of acid, exothermic reaction of concentrated acid
and water, ‘holding up‘ of vapour in reflux condenser.
Data:
Precautions 2
-3 e.g. gloves and goggles, gentle heating during reflux, no naked flame
Densities: Butan-2-ol = 0.8 gcm
near flammable solvents, careful addition of chemicals.
2-bromobutane = 1.3 gcm-3
Total = 30 marks.
Water = 1.0 gcm-3
Conc. Hydrochloric acid = 1.2 gcm-3
Sulphuric acid and water mix = 1.4 gcm-3
Boiling points: 2-bromobutane = 91 oC

2-chlorobutane = 78 oC
Acknowledgements: This Factsheet was researched and written by Kieron Heath. Curriculum
Press, Unit 305B, The Big Peg, 120 Vyse Street, Birmingham, B18 6NF. ChemistryFactsheets
may be copied free of charge by teaching staff or students, provided that their school is a
registered subscriber. No part of these Factsheets may be reproduced, stored in a retrieval
system, or transmitted, in any other form or by any other means, without the prior permission
of the publisher. ISSN 1351-5136
4
Chem Factsheet
April 2003 Number 52
Reactions of Functional Groups - A Summary
To succeed in this topic you need to: Reactions of alkenes
• Be able to recall and write out the functional groups represented
in this Factsheet; CO2 + H2O
• Have a thorough knowledge of the organic reactions and their Alkane
conditions (described in the Organic Chemistry Factsheets to H2 O2
electrophilic heat Di-halogenoalkane
date 27, 31, 32, 33, 34 and 39); heat,
addition
• Recognise the summarised versions of the equations in this Ni catalyst halogen electrophilic
Alkenes addition
Factsheet and be able to write them out in full under exam
conditions.
alkaline hydrogen
KMnO4(aq) halide Halogenoalkane
After working through this Factsheet you will: Diol
• Have revised the organic chemistry reactions that candidates electrophilic
oxidation addition
are required to learn for AS and A2 Chemistry modules. electrophilic addition
• Have a reference paper as you start to work through questions
on organic pathways and synthesis.
Reactions of alcohols
This Factsheet is designed to be used as a revision aid as candidates set
about the sometimes daunting task of learning all of the organic reactions bromo-alkane
required by the A2 Chemistry course.
nucleophilic substitution
These spider diagrams represent the reactions in a summarised version, in chloro-alkane iodo-alkane
a visual fashion that suits many learners. They should be used in NaBr(s) +
nucleophilic H2SO 4(conc.) nucleophilic
conjunction with Factsheets 27, 31, 32, 33, 34 and 39, which show the substitution to make HBr
reactions in a more detailed format. substitution
A good way of using this Factsheet to revise effectively would be as

dry PCl5 P(s) + I2(s)
follows: to make PI 3
1. Pick a group to revise (e.g. alkanes).
2. Pick a member of that group at random (e.g. propane). halogenation
3. Use the spider diagram to help you write out balanced chemical
reactions, with conditions, for the organic chemical you have chosen.
(e.g.) Propane and oxygen (combustion)
heat
Alcohol
C3H8 + 5O2 3CO2 + 4H2O
dehydration
Propane and chlorine (free radical substitution) oxidation
uv light
C3H8 + Cl2 C3H7Cl + HCl
conc. H2SO4 heat to primary
170 o C alcohols
In an exam, candidates are required to apply their knowledge of organic secondary
reactions to a wide variety of compounds, so the more of these you do, the alcohols
better!
Cr2O72−(aq) H+(aq)
Reactions of alkanes alkene Cr2O72−(aq) H+(aq)
aldehyde ketone
Carbon Dioxide O2 halogen Halogeno
Alkanes further oxidation
+ Water heat UV Light alkane
free radical Cr2O72−(aq) H+(aq)
combustion
substitution
carboxylic
acid
1
Reactions of Functional Groups - A Summary Chem Factsheet
Fig. 3 Halogenoalkane reactions Ester Reactions
Nitrile Alcohol
Carboxylic acid H 2O H 2O Carboxylic acid
nucleophilic nucleophilic
KCN in + Ester +
substitution NaOH(aq) substitution
water/ethanol Alcohol Alcohol
heat under acid alkaline
heat under reflux conditions conditions
reflux
Halogenoalkane
KOH in
NH3 in
ethanol
ethanol heat under Acyl Chloride Reactions
heat
reflux
Amines Alkene
nucleophilic nucleophilic Carboxylic
substitution elimination acid Ester
nucleophilic nucleophilic
Grignard Reagents substitution substitution
Preparation H 2O alcohol
Mg turnings
Grignard Reagent
Halogenoalkane Acyl
Dry ether solvent
"R-MgHal"
Chloride
Boil under reflux addition
primary
Reactions amine NH3
Primary
Alcohol N-substituted Amide
nucleophilic Amide
addition / hydrolysis nucleophilic
nucleophilic
substitution
substitution
methanal,
CH2=O(g) then use Secondary
Alkane Reactions of Aldehydes
+ H2O(l) dilute acid Alcohol
nucleophilic for hydrolysis
substitution nucleophilic
addition / hydrolysis Primary
H 2O H+(aq) Alcohol
Hydroxy-nitrile
aldehyde (not methanal) compound reduction Primary
Grignard Reagent + H2O(l)
"R-MgHal" nucleophilic addition Alcohol
CO2 (g) reduction
NaBH4 in
+ H2O(l) ketone H+(aq) trace of ethanol
H+(aq) + H2O(l) HCN
KOH LiAlH4
in ether
Carboxylic Tertiary
Aldehydes
Acid Alcohol 2,4-DNP in Fehlings
ethanol solution
nucleophilic nucleophilic H2SO4 silver
addition / hydrolysis addition / hydrolysis nitrate in
warm
2,4-DNP ammonia
warm
Derivative solution
Carboxylic Acid Reactions Positive Fehlings
nucleophilic Test
Polyester addition then Positive Silver redox
elimination Mirror Test
nucleophilic substitution /
Ester polymerisation redox
nucleophilic
Alcohol
substitution Diacid LiAlH4 reduction
alcohol + H+(aq) then
Diol H+(aq)
boil under reflux
conc. H2SO4 LiAlH4 in
dry ether
Carboxylic
Na2CO3 Acid
or NaHCO 3 PCl5
dry
aqueous
Sodium Salt + Acyl Chloride
CO2 + H2O nucleophilic
neutralisation substitution
2
Reactions of Functional Groups - A Summary Chem Factsheet
Reactions of Aldehydes Reactions of Amino Acids
Secondary acid alkali

Alcohol Salt Amino Acids Salt
Hydroxy-nitrile
compound reduction Secondary neutralisation neutralisation
nucleophilic addition Alcohol

reduction Reactions of Phenol
NaBH4 in
trace of HCN ethanol
KOH LiAlH4 2,4,6-
in ether
Phenate ion tribromophenol
Ketones
neutralisation electrophilic substitution
-
2,4-DNP in OH (aq)
H2SO4 Br 2(aq)
Phenol
2,4-DNP
Derivative
acyl chloride,
nucleophilic addition then
in NaOH(aq)
elimination
Reactions of Amines Ester

Substituted
Salts Amides
Reactions of Benzene
nucleophilic addition / nucleophilic
neutralisation substitution
Bromobenzene
acid electrophilic substitution
acyl chloride
Amines Br2 Fe cat.
dry
primary amines + acyl chlorides
if monomers contain 2 amine
groups and 2 acyl chloride groups Benzene
50o C conc
H2SO4 Fe cat. dry
Polyamides HNO3 Br2
polymerisation
Nitrobenzene Alkylbenzene
electrophilic substitution electrophilic substitution
Reactions of Nitrites
Sn, in alkali
Carboxylic alkali acid Carboxylic conc. HCL, KMnO 4 heat under
Nitriles NaOH reflux
acid salt acid
heat under heat under
hydrolysis reflux reflux hydrolysis
LiAlH4 Phenylamine Benzocarboxylic
in ether reduction acid
oxidation
Amine HNO2
+
reduction HCl
Benzenediazonium
Reactions of Amides
ions
Br2(l) +
P4 O10 NaOH(aq) Amine +
Nitrile Amides Acknowledgements: This Factsheet was researched and written by Kieron Heath
warm warm CO2
Curriculum Press, Unit 305B, The Big Peg, 120 Vyse Street, Birmingham, B18 6NF
dehydration
hydrolysis ChemistryFactsheets may be copied free of charge by teaching staff or students, provided that
their school is a registered subscriber. No part of these Factsheets may be reproduced, stored
in a retrieval system, or transmitted, in any other form or by any other means, without the
prior permission of the publisher. ISSN 1351-5136

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GCE

Edexcel Advanced Subsidiary GCE in Chemistry (8CH01)

Edexcel Advanced GCE in Chemistry (9CH01)

Authorised by Roger Beard

2 — Activity b: Qualitative observation 5

3 — Activity c: Quantitative measurement 7

1.2 Conditions under which assessments are to be carried out

1.4 Health and safety

2.1 Recording observations

Possible change Example of observation

2.2 Making inferences from observations

Apparatus Precision of reading

The following points are important.

26.50 + 26.25 + 26.60 + 26.65

26.50 + 26.60 + 26.65

The following points will apply.

the uncertainty in the equipment

3.5 Assumed laboratory skills

Instead of completing activities c and d separately, students could complete a multi-stage

A — Inorganic compounds and elements

• Coloured crystalline substances are usually hydrated salts of transition metals.

Colour Possible transition metal ions in salt

Colour Possible identity

Flame colour Inference

* Further tests would be needed to distinguish these ions.

• Gases or vapours may be evolved on heating a solid compound.

Gas or vapour Possible source

* Bromine dissolves in organic solvents to form a brown solution whereas nitrogen

5 Action of dilute acids

Action of acid Possible source

Reducing agents usually:

Oxidizing agents usually:

7 Hydrogen peroxide solution

Observation on adding H2O2 Inference

pale green solution turns yellow iron(II) to iron(III) in acid solution

green precipitate turns brown iron(II) hydroxide to iron(III) hydroxide

green alkaline solution goes yellow chromium(III) to chromate(VI)

brown solution or black precipitate iodine from iodide in acid solution

1 Sodium hydroxide solution

• When dilute sodium hydroxide (NaOH) solution is added to a solution containing a

Observation on adding dilute Observation on adding Likely ion

green precipitate precipitate is insoluble nickel(II)

blue precipitate precipitate is insoluble copper(II)

white precipitate precipitate dissolves to a zinc(II)

no precipitate but ammonia ammonium

Observation on adding dilute Observation on adding excess Likely ion

3 Barium chloride solution

Anion Precipitate Addition of dilute HCl

Anion Precipitate Addition of aqueous NH3

5 Concentrated sulfuric acid

Halide Observations on adding Observed reaction

bromide steamy fumes, brown vapour, HBr, Br2 (SO2)

Students will always be told if a compound, or mixture of compounds, to be identified is

Solubility of compound Possible identity pH of Possible

Igniting an organic unknown on a crucible lid may help in identifying it.

Observation Possible inferences

burns with a clean flame saturated low molar mass compound

no residue most lower molar mass compounds

Test Observation Inference

phosphorus(V) chloride steamy fumes of OH group in alcohols

2,4−dinitrophenylhydrazine solution orange precipitate C=O group in

boil with Fehling’s or Benedict’s blue solution gives aldehyde

warm with ammoniacal silver nitrate silver mirror aldehyde