Chemical

Tests

Examiners love asking questions on simple chemical tests, particularly the organic ones.

These should be very easy marks. One way to remember them is to compile a list (see below) on one
piece of paper and look over them for a few minutes a day. You will see that there are not that many
tests.


Aldehyde/ketone: Brady's Reagent (also known as 2,4-dinitrophenylhydrazine or 2,4-DNP)

to test for a carbonyl group in an aldehyde or ketone

Test result: if an aldehyde or ketone is present a bright orange precipitate forms. You can then take
the melting point of the precipitate and compare it to the literature value.

Edexcel: you dont need to know the structure of the reagent or precipitates but there have been the
occasional question on structures. You might as well know that 2,4-DNP is a nitrogen nucleophile and the
precipitate contains a C=N bond. It is a nucleophilic reaction.


Aldehyde/ketone: Fehling's/ Benedicts Solution and Tollen's Reagent

to distinguish between an aldehyde and a ketone

Fehling's/Benedicts: Fehlings solution is Cu(II) ions dissolved in NaOH (blue solution). Benedicts is also
Cu(II) solution but dissolved in Na2CO3.

Test results: both give a red coloured copper(I) oxide precipitate when heated with an aldehyde, a
ketone won't react.

Tollen's (the silver mirror test): the reagent is silver nitrate dissolved in aqueous ammonia.

Test result: Tollens solution is heated with the aldehyde leaving a silver mirror on the test tube. A
ketone won't react.

Note: these are all redox reactions. The aldehyde is oxidised to a carboxylic acid and the Cu(II) ions are
reduced to Cu(I) for Fehlings/Benedicts and in Tollens, the Ag+ ion is reduced to Ag. The ketone doesnt
react as it cannot be oxidised any further.


Methyl carbonyl: Iodoform reaction (Edexcel)

to identify a methyl-carbonyl group

Test result: a methyl ketone is reacted with iodine in NaOH solution to give pale yellow crystals and an
antiseptic smell. The crystals formed are CHI3 (iodoform).

Sometimes they ask about the other products, so here is an equation of all the products:

CH3COCH3 + 3I2 + 4NaOH CHI3 + CH3COONa + 3NaI + 3H2O

Note: you can also do this reaction with a secondary alcohol. The iodine will oxidise the alcohol to the
ketone first and then you proceed as above.


Alcohol: add PCl5 (Edexcel and AQA)

to identify a hydroxyl group

Test result: misty fumes of HCl are given off which turn damp blue litmus paper red.


ROH + PCl5 RCl + HCl(g) + POCl3


Note: this reaction also occurs for carboxylic acids. You would use the test below to distinguish between
an alcohol and an acid.

K2Cr2O7: also test for an alcohol as dichromate is reduced and changes colour from orange to green.

Carboxylic acid: add sodium hydrogencarbonate

to identify a carboxylic acid

Test result: CO2 is given off, which of course turns lime water milky.

RCOOH + NaHCO3 RCOONa + H2O + CO2


Acyl Chloride (AQA and Edexcel): can react with water to give HCl, which can be detected as misty
fumes.

Haloalkane: add silver nitrate (from AS)

Test result: warm the solution with NaOH then acidify with nitric acid. Add silver nitrate solution and you
will get a precipitate:
white = chloro (AgCl)
cream = bromo (AgBr)
yellow = iodo (AgI)

The problem with this test is that it can be difficult to distinguish between the colours. You can then add
NH3 solution to confirm the identity.

Add dilute NH3 solution only the chloride will dissolve.

Add concentrated NH3 solution the bromide will dissolve.
The iodide is insoluble in both NH3 solutions.