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Doc Brown's Chemistry Qualitative Methods of Analysis Revision Notes
Doc Brown's Chemistry Revising Advanced Organic Chemistry
Chemical identification TESTS Part 2 Qualitative tests to identify organic molecule functional groups
Functional group tests for alkenes RCH=CHR, hydroxy group functional group primary, secondary & tertiary alcohols
ROH, phenols, carboxylic group RCOOH, acyl/acid amide group RCONH
2
, acyl/acid chloride group RCOCl, aliphatic amine group RNH
2
, aryl/aromatic
amine, aldehyde functional group RCHO, ketone functional group RCOR, halogenoalkanes/haloalkanes (chloroalkane, bromoalkane, iodoalkane) R
Cl, RBr, RI, esters RCOOR and the iodoform test CHI
3
also = Part 11 Qualitative Analysis Test for and identify organic functional groups notes
Part 1 Introduction
Part 2 Qualitative tests to identify organic molecule functional groups of homologous series (this page)
Part 3 Metal cations (positive ions), metal carbonates, ammonium ion and hydrogen ions (acids)
Part 4 Gases, water and nonmetallic elements
Part 5 Anions (negative ions) including hydroxide (alkalis)
some associated revising links
GCSE/IGCSE Revision Qualitative Analysis Quiz on chemical test methods for identifying ions, gases and compounds
Quantitative analysis: acidbase, silver nitratechloride, EDTA titrations * Quantitative analysis: Redox titrations
Full list of KEYWORDS for inorganic/organic identification methods in alphabetical order e.g. test/reagent for: * acid ==> H
+
* acid/acyl chloride RCOCl
* alcohols general ROH/prim RCH
2
OH/sec R
2
CHOH/tert R
3
COH) * aldehyde RCHO * prim aliphatic amine RNH
2
* aliphatic/aromatic carboxylic acids *
alkali ==> OH

* alkane/alkene >C=C</alkyne C C (saturated versus unsaturated) * aluminium/aluminum ion Al

3+
* amide RCONH
2
* prim aliphatic
amines RNH
2
* ammonia gas NH
3
* ammonium ion NH
4
+
* prim aromatic amine C
6
H
5
NH
2
etc. * barium ion Ba
2+
* Benedict's solution * Brady's
reagent * bromide ion Br

* bromine Br
2
* caesium ion Cs
+
* calcium ion Ca
2+
by flame or hydroxide ppt. * carbonate CO
3
2
/hydrogencarbonate HCO
3

with acid or effect of heating metal carbonate e.g. MCO

3
* carbon dioxide gas CO
2
* carboxylic acid RCOOH * carboxylic acid (aliphatic) salts e.g.
RCOO

Na
+
* chloride ion Cl

* chlorine gas Cl
2
* Chomate(VI) ion CrO
4
2
* copper(II) ion Cu
2+
by flame or hydroxide ppt. * 24DNPH (for
aldehydes/ketones test) * esters RCOOR * Fehlings test/solution * flame test for metal ions * fluoride ion F

* haloalkanes/halogenoalkanes RX *
hydrogen gas H
2
* hydrogen sulphide H
2
S * hydrogen ion, acids H
+
* hydrogen bromide gas/hydrobromic acid HBr * hydrogen chloride
gas/hydrochloric acid HCl * hydrogen iodide gas/hydriodic acid HI * hydroxide ion, alkali OH

* hydroxy/alcohol/phenol (organic) * iodide ion I

*
iodine I
2
* iodoform test formation of CHI
3
* iron(II) ion Fe
2+
* iron(III) ion Fe
3+
* ketone R
2
C=O * lead(II) ion Pb
2+
* lithium ion Li
+
* lime water
Ca(OH)
2(aq)
* magnesium ion Mg
2+
* metal carbonatesheating e.g. MCO
3
* metal ions via hydroxide precipitate * nitrate or nitrate(V) NO
3

* nitrite or
nitrate(III) NO
2

* nitrogen dioxide or nitrogen(IV) oxide NO

2
* oxygen gas O
2
* phenols C
6
H
5
OH etc. * potassium ion K
+
* rubidium ion Rb
+
* reducing
sugars * saturated/unsaturated * silver nitrate AgNO
3
(see chloride, bromide, iodide tests) * sugars (reducing) * sodium ion Na
+
* strontium Sr
+
*
'sulphate/sulfate' or sulphate(VI) SO
4
2
* sulphide S
2
* 'sulphite/sulfite' or sulphate(IV) SO
3
2
* sulphur dioxide gas SO
2
* Tollen's Reagent *
unsaturated/saturated * water H
2
O * zinc ion Zn
2+
*
IIT JEE 2015
Preparation
plancessjee.com
330 hrs of videos by Top IITians Free
IITian mentor for Guidance
Use the alphabetical test list above for identifying anions, cations, gases, molecules etc. to find what you require! for your KS3KS4 ScienceGCSE
IGCSE Chemistry and GCEASA2IBUS grades 912 K12 advanced subsidiary chemistry course etc. and help you to identify unknown inorganic
and organic compoundsmolecules for qualitative analysis.
EMAIL query?comment?test missing? * Gas Preparations * Hazard warning signs/symbolsexamples of labelling

2. Qualitative ORGANIC functional group tests in various homologous series
CHEMICAL TEST FOR TEST METHOD OBSERVATIONS TEST CHEMISTRY and comments
ALKENE or alkyne
chemical test i.e. any
nonaromatic
unsaturated
hydrocarbon with a double or
triple carboncarbon bond.
Bubble gas through, or add
liquid to, a solution of bromine
in hexane or water.
The orange/brown bromine
rapidly decolourises, as a
saturated colourless organic
bromocompound is formed.
R
2
C=CR
2
+ Br
2
==> BrR
2
CCR
2
Br
RC CR + 2Br
2
==> Br
2
RCCRBr
2
R = H, alkyl or aryl
Saturated alkanes give no fast reaction with bromine.
Hydroxy group ROH
chemical test in
alcohols and phenols
(in 'dry' conditions*)

The first 3 tests (i) (iii) given
on the right are quite general
for most alcohols.
(i) Mix it with a few drops of
ethanoyl chloride, test fumes
with litmus and silver nitrate (*
note ethanoyl chloride reacts
with water, phenols and amines
too!).
(ii) Mix it with a little
phosphorus(V) chloride and test
as above.
(iii) Warm with a little ethanoic
acid and a few drops of conc.
sulphuric acid. Pour into water.
(i) Litmus turns red and a white
precipitate with silver nitrate
(aq)
(drop on end of glass rod), if the
mixture is poured into water you
may detect a 'pleasant' ester
odour, can test for HCl but water
and amines produce it too!
(ii) as for (1) but no ester smell!
(iii) You should get a 'pleasant'
characteristic smell of an ester.
(i) ROH + CH
3
COCl ==> CH
3
COOR + HCl
An ester and hydrogen chloride are formed
(ii) ROH + PCl
5
==> RCl + POCl
3
+ HCl
a chloro compound and hydrogen chloride are formed.
(i) and (ii) Ag
+
(aq)
+ Cl

(aq)
==> AgCl
(s)
from the hydrogen
chloride fumes dissolved in water.
(iii) CH
3
COOH + ROH ==> CH
3
COOR + H
2
O
Primary alcohol chemical test
RCH
2
OH, R = H, alkyl or aryl
(NOT a phenol).
(ii) is not a good test on its
own, since so many other
readily reducible organic
compounds will give the same
reaction, though following it up
by testing for an aldehyde gives
it much more validity.
(i) Lucas test shake a few
drops with cold zinc chloride in
conc. HCl
(aq)
(ii) Distil with potassium
dichromate(VI) and mod. conc.
H
2
SO
4(aq)

(i) Solution remains clear.
(ii) If product distilled off
immediately an aldehyde odour
can be detected and the
solution colour changes from
orange to green.
(i) Not usually reactive enough to form a primary halogenoalkane
(ii) RCH
2
OH + [O] => RCHO + H
2
O or the full works! 3R
CH
2
OH + Cr
2
O
7
2
+ 8H
+
==> 2Cr
3+
+ 3RCHO + 7H
2
O
The orange dichromate(VI) ion is reduced to the green
chromium(III) ion. If the organic product is collected you could
test for an aldehyde.
Secondary alcohol chemical
test
R
2
CHOH, R = alkyl or aryl.
(ii) is not a good test on its
own, since so many other
reducible organic compounds
will give the same reaction,
though following it up by testing
for a ketone gives it much more
validity.
(i) Lucas test.
(ii) Distil with
K
2
Cr
2
O
7
/H
2
SO
4(aq)

(i) Solution may cloud very
slowly or remains clear (hit and
miss)
(ii) If product distilled off
immediately a ketone odour
can be detected and the
solution colour changes from
orange to green.
(i) May be reactive enough to slowly form an insoluble secondary
halogenoalkane: R
2
CHOH + HCl => R
2
CHCl + H
2
O
(ii) R
2
CHOH + [O] => RCOR + H
2
O or the full works!
3R
2
CHOH + Cr
2
O
7
2
+ 8H
+
==> 2Cr
3+
+ 3RCOR + 7H
2
O
The orange dichromate(VI) ion is reduced to the green
chromium(III) ion. If the organic product is collected you could
test for an aldehyde.
Tertiary alcohol chemical test
R
3
COH, R = alkyl or aryl.
(i) Lucas test.
(ii) Distil with
K
2
Cr
2
O
7
/H
2
SO
4(aq)

(i) Goes cloudy very quickly.
(ii) No aldehyde or ketone
readily formed
(i) Reactive enough to immediately form an insoluble tertiary
halogenoalkane R
3
COH + HCl => R
3
CCl + H
2
O
(iii) Stable to modest oxidation.
Phenols (OH group is
attached directly to
aromatic ring)
chemical test. ROH, where R
is aryl e.g. C
6
H
5
OH
Add a few drops of iron(III)
chloride solution to a little of the
phenol in water.
Usually gives a purple colour. (see also test for primary aromatic amines use it in reverse
starting with a known primary aromatic amine!)
Carboxylic acids chemical
test
RCOOH
Mix the carboxylic acid with
water and add a little sodium
hydrogencarbonate solid or
solution.
fizzing, colourless gas gives
white precipitate with limewater
RCOOH + NaHCO
3
==> RCOONa + H
2
O + CO
2
(see also salts of aliphatic carboxylic acids below)
Salts of aliphatic carboxylic
acids e.g. RCOO

Na
+
or
Add a little dilute
hydrochloric/sulfuric acid to a
The solid or solution should
have no strong odour, but after
The stronger acid, HCl/H
2
SO
4
displaces the weaker aliphatic
carboxylic acid which have strongpungent characteristic
(RCOO

)
2
Mg etc.
suspected salt of an aliphatic
carboxylic acid.
adding the mineral acid you
should get a pungent odour of
the original aliphatic acid. If its
the salt of an aromatic
carboxylic acid, you get little
odour and maybe a white
crystalline precipitate.
odours e.g.
ethanoic acid from an ethanoate salt (smell of acetic acid,
vinegar) and butanoates release butanoic acid (butyric acid,
rancid odour).

Acid or Acyl Chloride
chemical test
RCOCl
Fumes in air forming HCl
(g)
(i) Add a few drops to water,
test with litmus and silver nitrate
solution.
(ii) Add to a little ethanol and
pour the mixture into water.
(i) Litmus turns red and a white
precipitate with silver nitrate.
(ii) As above and you may
detect a 'pleasant' ester odour.
(i) RCOCl + H
2
O ==> RCOOH + HCl
The acid chloride is hydrolysed to form HCl acid (chloride ions)
and the original carboxylic acid.
(ii) CH
3
CH
2
OH + RCOCl ==> RCOOCH
2
CH
3
+ HCl, an ethyl
ester and hydrogen chloride are formed
Acid Amide chemical test
RCONH
2
Boil the suspected amide with
dilute sodium hydroxide
solution, see in inorganic for
ammonia tests.
ammonia evolved on boiling (no
heat required to form ammonia,
if it was an ammonium salt)
RCONH
2
+ NaOH ==> RCOONa + NH
3
Aliphatic amines (primary,
where R = alkyl) chemical test
RNH
2

e.g. CH
3
CH
2
CH
2
NH
2
(i) Lower members soluble in
water but a very fishy smell! test
with red litmus and conc.
HCl(aq) fumes.
(ii) If a suspected salt of an
amine, then add sodium
hydroxide solution to free the
amine.
(i) A fishy odour, litmus turns
blue, white clouds with HCl.
(ii) The above is not observed
until after adding the alkali.
(i) Unless its a liquid or solid, only the more fishy odour
distinguishes it from ammonia.
(ii) The reaction is e.g.
RNH
3
+
+ OH

==> RNH
2
+ H
2
O

Aromatic amines
chemical test (where
R = aryl with the
amine or amino group directly
attached to an aromatic ring) R
NH
2
e.g. C
6
H
5
NH
2
(i) Dissolve the primary aromatic
amine in dilute hydrochloric acid
at 5
o
C and mix with sodium
nitrite solution.
(ii) Add a phenol dissolved in
dilute sodium hydroxide.
(i) It should be a clear solution
with few, if any, brown fumes.
(ii) A coloured precipitate [red
brown yellow etc.]
(i) If a primary aromatic amine, a 'stable' diazonium salt is
formed. Diazonium salts from aliphatic amines decompose
rapidly evolving colourless nitrogen.
(ii) An azo dyestuff molecule is formed in a coupling reaction e.g.
C
6
H
5
N=NC
6
H
4
OH
Aldehydes chemical test (R
CHO, R = H, alkyl or aryl) to
distinguish from ketones
(R
2
C=O, R = alkyl or aryl) and
also reducing sugars.
Note
(1) Test (b)(i) and (ii) can be
used to distinguish aldehydes
(reaction) and ketones (no
reaction).
(2) Aromatic aldehydes do NOT
give a positive result with (b)(ii)
Benedict's or Fehling's reagent).
(3) Reducing sugars may also
give a positive test with (b)(i)/(ii)
reagent e.g. glucose
(aldohexose) but not fructose?
(ketohexose)?
(a) Add a few drops of the
suspected carbonyl compound
to Brady's reagent (2,4
dinitrophenylhydrazine
solution)
(a) A yelloworange precipitate
forms with both types of
carbonyl compound.
The aldehyde or ketone 2,4dinitrophenylhydrazone is formed
R
2
C=O + (NO
2
)
2
C
6
H
3
NHNH
2
==>
(NO
2
)
2
C
6
H
3
NHN=CR
2
+ H
2
O
(R = H, alkyl or aryl)
This tells you its an aldehyde or ketone, but can't
distinguish them, read on below!
(b)(i) warm a few drops of the
compound with Tollens'
reagent [ammoniacal silver
nitrate]
(b)(ii) simmer with Fehling's or
Benedicts solution [a blue
complex of Cu
2+
(aq)
]
(b) Only the aldehyde produces
(i) A silver mirror on the side of
the test tube.
(ii) A brown or brick red ppt.
Aldehydes are stronger reducing agents than ketones and reduce
the metal ion and are oxidised in the process
i.e. RCHO + [O] ==> RCOOH
(i) reduction of silver(I) ion to silver metal
RCHO + 2Ag
+
+ H
2
O ==> RCOOH + 2Ag + 2H
+
(ii) reduction of copper(II) to copper(I) i.e. the blue solution of the
Cu
2+
complex changes to the brown/brick red colour of insoluble
copper(I) oxide Cu
2
O.
RCHO + 2Cu
2+
+ 2H
2
O ==> RCOOH + Cu
2
O + 4H
+
With (b)(i)/(ii) no reactions with ketones.
Halogenoalkanes
(haloalkanes) chemical test R
X where R = alkyl, X = Cl, Br
or I
The halide is covalently bound
(CX bond), so the halogen X
cannot react with the silver ion
(i) Warm a few drops of the
haloalkane with aqueous
ethanolic silver nitrate solution,
the ethanol increases the
solubility of the immiscible
haloalkanes.
(ii) Gently simmering a few
drops with aqueous NaOH (may
(i) Observe colour of precipitate
and the effect of ammonia
solution on it (for rest of details
see the (i) notes for chloride,
bromide and iodide tests
above in inorganic)
(ii) see the (i) notes as above
for more details.
(i) AgNO
3
+ RX ==> RNO
3
? + AgX
(s)
(ii) The sodium hydroxide converts the halogen atom into the
ionic halide ion in a hydrolysis reaction.
RX
(aq)
+ NaOH
(aq)
==> ROH
(aq)
+ NaX
(aq)
then Ag
+
(aq)
+ X

(aq)
==> AgX
(s)
to form the ionic Ag
+
X

(s)
precipitate until it is converted to
the 'free' X

ionic form. Note that

aromatic halogen compounds
where the X is directly attached
to the ring, do NOT readily
hydrolyse in this way and no
AgX ppt. will be seen. Aromatic
CX is a stronger bond than
aliphatic CX.
need to add ethanol to increase
solubility and reaction rate). Add
dilute nitric acid followed by
aqueous silver nitrate solution.
The addition of dilute nitric acid prevents the precipitation of other
silver salts or silver oxide (e.g. Ag
2
O forms if solution alkaline).

Esters chemical test RCOOR'
R = H, alkyl or aryl
R' = alkyl or aryl
There is no simple test for an
ester. Usually a colourless
liquid with a pleasant 'odour'.
The ester can be reacted with
saturated ethanolic
hydroxylamine hydrochloride +
20% methanolic KOH and
gently heated until boiling. Then
mixture acidified with 1M HCl
(aq)
and FeCl
3(aq)
added dropwise.
Deep red or purple colour
formed. The test depends on the
formation of a hydroxamic acid
RC(=NOH)OH which forms
coloured salts with Fe
3+
(aq)
ion.
The reaction is also given by acid chlorides and acid anhydrides,
and phenols give a purple colour with iron(III) chloride, so frankly,
the test is not that good. This test is not likely to be expected
Iodoform test
The formation of CHI
3
,
triiodomethane (or old name
'iodoform'.
NaOH
(aq)
is added to a solution
of iodine in potassium iodide
solution until most of the colour
has gone. The organic
compound is warmed with this
solution.
A yellow solid is formed with the
smell of an antiseptic, CHI
3
, tri
iodomethane, melting point
119
o
C.
This reaction is given by the alcohol ethanol CH
3
CH
2
OH and all
alcohols with the 2ol structure CHOHCH
3
and
the aldehyde ethanal CH
3
CHO and all ketones with the 2one
structure RCOCH
3
('methyl ketones')
Its a combination of halogenation and oxidation and is not a
definitive test for anything, it just indicates a possible part of a
molecules structure.

Keywords & phrases: What is the test for alkenes? How do you test for an alkene functional group? What is the test for unsaturation? How do you test for
unsaturation? What is the test for alcohols? How do you test for an alcohol functional group? What is the test for a primary alcohol? How do you test for a primary
alcohol? What is the test for a secondary alcohol? how do you test for a secondary alcohol? What is the test for a tertiary alcohol? How do you test for a tertiary
alcohol? What is the test for a phenol? How do you test for a phenol? What is the test for a phenolic group? How do you test for a phenolic functional group? What is
the test for a carboxylic acid? How to you test for a carboxylic acid functional group? What is the test for a salt of a carboxylic acid? how do you test for the salt of a
carboxylic acid? What is the test for an acid/acyl chloride? How do you test for an acid/acyl chloride functional group? What is the test for an acid amide? how do
you test for an acid amide? What is the test for an aliphatic amine? How do you test for aliphatic amines? What is the test for a primary amine? How do you test for
a primary amine functional group? What is the test for a secondary amine? How do you test for a secondary amine? What is the test for a tertiary amine? How do
you test for a tertiary amine? What is the test for an aromatic amine? How do you test for an aromatic amine? What is the test for aldehydes? How do you test for an
aldehyde functional group? What is the test for ketones? How do you test for a ketone functional group? What is the test for reducing sugars? How do you test for a
reducing sugar? What is the test for a haloalkane? (tests for halogenoalkanes, 'alkyl halides') How do you test for a haloalkane functional group? What is the test for
a primary haloalkane? How do you test for a primary haloalkane? What is the test for a secondary haloalkane? How do you test for secondary haloalkane? What is
the test for a tertiary haloalkane? How do you test for a tertiary haloalkane? What is the test for an ester? How do you test for the ester functional group? What is the
iodoform test? (triiodomethane formation) How do you do the iodoform test? What does the iodoform reaction test for?
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