15 The synthesis of organic compounds Data sheet

Tests and observations on organic compounds

Preliminary tests
Preliminary observations and tests provide a general introduction
to the characteristics of a compound. They can include:

Many organic chemicals are
highly flammable. Take care
to avoid accidental ignition.
the state and appearance of the compound at room
temperature
the solubility of the compound in cold and hot water and the
pH of any solution that forms
the effect of heating the compound and the appearance of the
flame if the sample burns.

Specific tests
The main changes and observations to look for in organic
chemistry include:
Note that the unknown
substances you are asked
liquids mixing many organic liquids do not mix with water.
Shaking an immiscible liquid with water can produce a cloudy
to test may be hazardous or
undergo hazardous emulsion.
reactions. Always wear eye
protection. Assume the
solids dissolving whether or not a solid is soluble in water,
highest level of hazard.
acids or alkalis can be very significant. First check to see if
Remember that the nature the solid dissolves in water and whether or not it affects the
of the hazard may vary with pH of the water. Then, test separate small samples with acid
the concentration of
solutions. and finally with alkali.
colour changes colour changes may be due to changes in the
colour of the solution, the formation of a coloured precipitate
or a combination of the two.
formation of precipitates in organic chemistry, the
appearance of a precipitate and its colour can be significant.
evolution of gases you are only likely to come across a
Hint limited range of gases when testing organic chemicals. The
Develop a language for most likely gases are carbon dioxide, hydrogen, ammonia,
describing common smells hydrogen chloride and water vapour. You should be proficient
with words such as sharp,
fruity, like an antiseptic, in confirming the identity of these gases from your AS course.
and so on. See the Data sheet: Tests for gases on the Dynamic Learning
Student website.
production of chemicals with distinctive smells smell is
particularly important in identifying esters.

The summaries that now follow describe the characteristic

properties and show the common tests that can help to identify
particular functional groups.
Smell gases and vapours
very cautiously. Never smell
a chemical directly or at the
mouth of its container.
Carefully waft some of the
vapour towards your nose
and inhale gently. Avoid
smelling chemicals if you
are asthmatic.
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15 The synthesis of organic compounds Data sheet

The characteristic properties and tests for different functional groups

Alkanes
Alkanes do not have a functional group in the usual sense of the
term. The reactions of alkanes are characteristic of CC and CH
bonds which are non-polar and inert to polar and ionic reagents.
Physical properties Solubility and acidbase character
C1C4 alkanes are gases. C5C17 alkanes are Alkanes do not mix with water. They are
colourless liquids, alkanes from C18 upwards inert to all aqueous reagents. No acidbase
are solids properties
Functional group tests
Test Observation Inference
Ignite the alkane Burns with a yellowish and Not a definitive test but
a clean or slightly smoky helps distinguish
flame alkanes from benzene
and related aryl
compounds which burn
with very smoky flames

Alkenes
Functional group:

Physical properties Solubility and acidbase character

Ethene, propene and the butenes are Alkenes, like other hydrocarbons, do not
colourless gases. Common alkenes with mix with or dissolve in water. They have no
more than four carbon atoms are liquids acidbase properties
Functional group tests
Test Observation Inference
Shake with dilute, aqueous Yellow/orange bromine is This test detects the
bromine rapidly decolorised. (A presence of alkene
hydrocarbon that is not an double bonds but other
alkene will simply extract compounds, such as
the bromine colour from phenols, can decolorise
the aqueous layer) bromine but form a
precipitate
Shake with a few drops of Purple colour quickly A compound that can
dilute, acidified potassium disappears reduce manganate(VII).
manganate(VII) Other organic
compounds give this
result

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15 The synthesis of organic compounds Data sheet
Halogenoalkanes
Functional group:
iodoalkane
Physical properties
Most common halogenoalkanes are
colourless liquids at room temperature
Functional group tests
Test
Warm with a solution of
sodium hydroxide, acidify
with nitric acid and then
add silver nitrate solution
Alcohols
Functional group:
tertiary
Physical properties
All common alcohols are colourless liquids
Functional group tests
Test
Add solid PCl5 to the
anhydrous compound
Warm with an acidic
solution of potassium
dichromate(VI)
G. Hill and A. Hunt 2009 Edexcel Chemistry for A2
chloroalkane bromoalkane
Solubility and acidbase character
Halogenoalkanes do not mix with water.
They have no acidbase properties
Observation Inference
A white, cream or yellow Hydrolysis with alkali
precipitate on adding silver produces halide ions
nitrate from covalent
molecules. In acid
solution, the silver ions
form precipitates:
white AgCl from a
chloroalkane; creamy
AgBr from a
bromoalkane and
yellow AgI from an
iodoalkane
primary secondary
Solubility and acidbase character
Alcohols with relatively short hydrocarbon
chains are soluble in water. Alcohols are
not acidic in aqueous solution
Observation Inference
Mixture fizzes and a The gas is hydrogen
colourless, fuming, acidic chloride from the
gas forms reaction of PCl5 with an
OH group. (PCl5 reacts
in a similar way with
OH groups in phenols
and carboxylic acids.)
Orange solution turns green Primary and secondary
and the vapour given off (but not tertiary)
has a stronger smell than alcohols are oxidised to
the alcohol more volatile aldehydes
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15 The synthesis of organic compounds Data sheet

or ketones

Mix equal volumes of Fruity smell Ester formed from the

alcohol and ethanoic acid. alcohol by reaction with
Add a few drops of ethanoic acid
concentrated sulfuric acid.
Warm and then pour into
excess sodium carbonate
solution

Aldehydes
Functional group:

Physical properties Solubility and acidbase character

Methanal is a gas at room temperature. The simpler aldehydes such as methanal
Ethanal boils at 21 C. All other common and ethanal are freely soluble in water.
aldehydes are colourless liquids They have no acid or base properties in
aqueous solution
Functional group tests
Test Observation Inference
Warm with freshly prepared Mixture turns green, then Aldehydes reduce
Fehlings solution the green colour goes and copper(II) ions in the
an orange-red precipitate reagent to copper(I)
forms oxide and are
themselves oxidised to
carboxylic acids
Warm with Tollens reagent Silver forms as a mirror on Aldehydes reduce
(ammoniacal silver(I) clean glass or as a dark grey silver(I) ions in the
nitrate) solid reagent to metallic
silver and are
themselves oxidised to
carboxylic acids
Add a solution of Thick yellow or red Characteristic reaction
2,4-dinitrophenylhydrazine precipitate forms of carbonyl compounds

Ketones
Functional group:

Physical properties Solubility and acidbase character

All common ketones are colourless liquids The simpler ketones such as propanone mix
at room temperature freely with water but have no acid or base
properties in aqueous solution

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Functional group tests

Test Observation Inference
Warm with freshly-prepared No reaction Ketones do not reduce
Fehlings solution Fehlings solution

Warm with fresh Tollens No reaction Ketones do not reduce

reagent Tollens reagent

Add a solution of Thick yellow or red Characteristic reaction

2,4-dinitrophenylhydrazine precipitate forms of carbonyl compounds
Warm with a solution of Pale yellow precipitate CHI3 formed from a
iodine in aqueous sodium forms ketone containing a
hydroxide CH3CO group

Carboxylic acids
Functional group:

Physical properties Solubility and acidbase character

The simplest carboxylic acids, such as The simpler acids dissolve in water. They
ethanoic acid, are colourless liquids. Other are weak acids.
common acids, such as ethanedioic acid They give a solution with a pH below 7
and benzenecarboxylic acid, are solid
Functional group tests
Test Observation Inference
Warm a little of the solid or Sharp or acrid smell Characteristic smell of
liquid with dilute carboxylic acids
hydrochloric acid Smell of vinegar Ethanoic acid and
ethanoates
Add a solution of sodium The mixture fizzes and Carbon dioxide given off by
carbonate gives off a colourless an acid
gas that turns
limewater milky white
Add ethanol and warm with Fruity smell detected Formation of an ester by
a drop of concentrated reaction of the acid with
sulfuric acid. Pour into ethanol
sodium carbonate solution
Add solid PCl5 to the Mixture fizzes and a The gas is hydrogen
anhydrous compound colourless, fuming, chloride from the reaction
acidic gas forms of PCl5 with an OH group
(PCl5 reacts in a similar way
with OH groups in alcohols
and phenols)

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Aromatic hydrocarbons (arenes)
Functional group:
Physical properties
Common hydrocarbons related to benzene
are liquids
Functional group tests
Test
Ignite the hydrocarbon
G. Hill and A. Hunt 2009 Edexcel Chemistry for A2
Solubility and acidbase character
Benzene and related hydrocarbons do not
mix with water. They have no acidbase
properties
Observation Inference
Burns with a yellow and Not a definitive test but
very smoky flame helps distinguish
benzene and related
aryl compounds from
other hydrocarbons
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