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QUALITATIVE ANALYSIS TESTS for identifying organic functional groups of homologous series of molecules identification

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CHEMICAL TESTS FOR IDENTIFYING ORGANIC FUNCTIONAL GROUPS

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 RCONH2, acyl/acid chloride group RCOCl, aliphatic amine group RNH2, aryl/aromatic amine, aldehyde
functional group RCHO, ketone functional group RCOR, halogenoalkanes/haloalkanes (chloroalkane, bromoalkane, iodoalkane) RCl, RBr, RI,
esters RCOOR and the iodoform test CHI3
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)
APPENDIX 1. IDENTIFYING ELEMENTS from LINE SPECTRA (non-chemical test method)
some associated revising links
GCSE/IGCSE Revision QUIZ on chemical tests for identifying ions, gases and compounds
A Level Quantitative analysis: acidbase, silver nitratechloride, EDTA titrations
A Level 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 RCH2OH/sec R2CHOH/tert R3COH) * aldehyde RCHO * prim aliphatic amine RNH2 * aliphatic/aromatic
carboxylic acids * alkali ==> OH * alkane/alkene >C=C</alkyne C

C (saturated versus unsaturated) * aluminium/aluminum ion Al3+ * amide

RCONH2 * prim aliphatic amines RNH2 * ammonia gas NH3 * ammonium ion NH4+ * prim aromatic amine C6H5NH2 etc. * barium ion Ba 2+ *
Benedict's solution * Brady's reagent * bromide ion Br * bromine Br2 * caesium ion Cs+ * calcium ion Ca 2+ by flame or hydroxide ppt. * carbonate
CO32/hydrogencarbonate HCO3 with acid or effect of heating metal carbonate e.g. MCO3 * carbon dioxide gas CO2 * carboxylic acid RCOOH *
carboxylic acid (aliphatic) salts e.g. RCOONa + * chloride ion Cl * chlorine gas Cl * Chomate(VI) ion CrO 2 * copper(II) ion Cu2+ by flame or
2

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 H2 * hydrogen sulphide H2S * 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 I2 * iodoform test formation of CHI3 * iron(II) ion Fe 2+ * iron(III) ion Fe 3+ * ketone R2C=O
* lead(II) ion Pb2+ * lithium ion Li+ * lime water Ca(OH)2(aq) * magnesium ion Mg2+ * metal carbonatesheating e.g. MCO3 * metal ions via
hydroxide precipitate * nitrate or nitrate(V) NO3 * nitrite or nitrate(III) NO2 * nitrogen dioxide or nitrogen(IV) oxide NO2 * oxygen gas O2 *
phenols C6H5OH etc. * potassium ion K+ * rubidium ion Rb+ * reducing sugars * saturated/unsaturated * silver nitrate AgNO3 (see chloride, bromide,
iodide tests) * sugars (reducing) * sodium ion Na + * strontium Sr+ * 'sulphate/sulfate' or sulphate(VI) SO42 * sulphide S2 * 'sulphite/sulfite' or
sulphate(IV) SO32 * sulphur dioxide gas SO2 * Tollen's Reagent * unsaturated/saturated * water H2O * zinc ion Zn2+ *

Use the alphabetical test list above for identifying anions, cations, gases, molecules etc. to find what you require! for your KS3KS4 Science
GCSEIGCSE Chemistry and GCEASA2IBUS grades 912 K12 advanced subsidiary chemistry course etc. and help you to identify unknown
inorganic and organic compoundsmolecules for qualitative analysis.

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QUALITATIVE ANALYSIS TESTS for identifying organic functional groups of homologous series of molecules identification
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
ALKENE or alkyne
chemical test i.e. any
nonaromatic
unsaturated
hydrocarbon with a double
or triple carboncarbon
bond.
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.

TEST METHOD
Bubble gas through, or add
liquid to, a solution of
bromine in hexane or water.

OBSERVATIONS

TEST CHEMISTRY and comments

The orange/brown bromine

R2C=CR2 + Br2 ==> BrR2CCR2Br
rapidly decolourises, as a
saturated colourless organic RC CR + 2Br2 ==> Br2RCCRBr2
bromocompound is formed.
R = H, alkyl or aryl
Saturated alkanes give no fast reaction with bromine.

(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.

(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) Warm with a little ethanoic

acid and a few drops of conc. (iii) You should get a
sulphuric acid. Pour into
'pleasant' characteristic smell
water.
of an ester.

Primary alcohol chemical

test

(i) ROH + CH3COCl ==> CH3COOR + HCl

An ester and hydrogen chloride are formed
(ii) ROH + PCl5 ==> RCl + POCl3 + 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) CH3COOH + ROH ==> CH3COOR + H2O

(i) Lucas test shake a few

(i) Solution remains clear.
drops with cold zinc chloride in
conc. HCl(aq)
(ii) If product distilled off
RCH2OH, R = H, alkyl or aryl
immediately an aldehyde
odour can be detected and the
(NOT a phenol).
(ii) Distil with potassium
dichromate(VI) and mod. conc. solution colour changes from
orange to green.
(ii) is not a good test on its
H2SO4(aq)
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) Not usually reactive enough to form a primary

halogenoalkane

Secondary alcohol chemical (i) Lucas test.

test
(ii) Distil with
R2CHOH, R = alkyl or aryl.
K2Cr2O7/H2SO4(aq)

(i) May be reactive enough to slowly form an insoluble

secondary halogenoalkane: R2CHOH + HCl => R2CHCl + H2O

(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.
Tertiary alcohol chemical
test
R3COH, R = alkyl or aryl.

(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) Lucas test.

(i) Goes cloudy very quickly.

(ii) Distil with

K2Cr2O7/H2SO4(aq)

(ii) No aldehyde or ketone

readily formed

(ii) RCH2OH + [O] => RCHO + H2O or the full works! 3R

CH2OH + Cr2O72 + 8H+ ==> 2Cr3+ + 3RCHO + 7H2O
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.

(ii) R2CHOH + [O] => RCOR + H2O or the full works!

3R2CHOH + Cr2O72 + 8H+ ==> 2Cr3+ + 3RCOR + 7H2O
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.

(i) Reactive enough to immediately form an insoluble tertiary

halogenoalkane R3COH + HCl => R3CCl + H2O
(iii) Stable to modest oxidation.

Phenols (OH group Add a few drops of iron(III)

is attached directly chloride solution to a little of
to aromatic ring)
the phenol in water.
chemical test. ROH, where
R is aryl e.g. C6H5OH

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

fizzing, colourless gas gives

white precipitate with
limewater

RCOOH + NaHCO3 ==> RCOONa + H2O + CO2

The solid or solution should

have no strong odour, but after
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.

The stronger acid, HCl/H2SO4 displaces the weaker

aliphatic carboxylic acid which have strongpungent
characteristic odours e.g.

RCOOH

Mix the carboxylic acid with

water and add a little sodium
hydrogencarbonate solid or
solution.

Salts of aliphatic carboxylic Add a little dilute

hydrochloric/sulfuric acid to a
acids e.g. RCOONa + or
suspected salt of an aliphatic

(RCOO )2Mg etc.

carboxylic acid.

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(see also salts of aliphatic carboxylic acids below)

ethanoic acid from an ethanoate salt (smell of acetic acid,

vinegar) and butanoates release butanoic acid (butyric acid,
rancid odour).

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QUALITATIVE ANALYSIS TESTS for identifying organic functional groups of homologous series of molecules identification

Acid or Acyl
Chloride chemical
test
RCOCl

(i) Add a few drops to water,

test with litmus and silver
nitrate solution.

(i) Litmus turns red and a

white precipitate with silver
nitrate.

(ii) Add to a little ethanol and

pour the mixture into water.

(ii) As above and you may

detect a 'pleasant' ester odour. (ii) CH3CH2OH + RCOCl ==> RCOOCH2CH3 + HCl, an ethyl
ester and hydrogen chloride are formed

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)

RCONH2 + NaOH ==> RCOONa + NH3

(i) Lower members soluble in

water but a very fishy smell!
test with red litmus and conc.
HCl(aq) fumes.

(i) A fishy odour, litmus turns

blue, white clouds with HCl.

(i) Unless its a liquid or solid, only the more fishy odour
distinguishes it from ammonia.

(ii) The above is not observed

until after adding the alkali.

(ii) The reaction is e.g.

Fumes in air forming HCl(g)

Acid Amide chemical test
RCONH2

Aliphatic amines (primary,

where R = alkyl) chemical
test RNH2
e.g. CH3CH2CH2NH2

Aromatic amines
chemical test
(where R = aryl with
the amine or amino group
directly attached to an
aromatic ring) RNH2

The acid chloride is hydrolysed to form HCl acid (chloride

ions) and the original carboxylic acid.

RNH3+ + OH ==> RNH2 + H2O

(ii) If a suspected salt of an

amine, then add sodium
hydroxide solution to free the
amine.

(i) Dissolve the primary

aromatic amine in dilute
hydrochloric acid at 5oC and
mix with sodium nitrite
solution.

(i) RCOCl + H2O ==> RCOOH + HCl

(i) It should be a clear solution (i) If a primary aromatic amine, a 'stable' diazonium salt is
with few, if any, brown fumes. formed. Diazonium salts from aliphatic amines decompose
rapidly evolving colourless nitrogen.
(ii) A coloured precipitate [red
brown yellow etc.]
(ii) An azo dyestuff molecule is formed in a coupling reaction
e.g.

e.g. C6H5NH2

(ii) Add a phenol dissolved in

dilute sodium hydroxide.

Aldehydes chemical test (R

CHO, R = H, alkyl or aryl) to
distinguish from ketones
(R2C=O, R = alkyl or aryl)
and also reducing sugars.

(a) Add a few drops of the

(a) A yelloworange
suspected carbonyl compound precipitate forms with both
to Brady's reagent (2,4
types of carbonyl compound.
dinitrophenylhydrazine
solution)

C6H5N=NC6H4OH
The aldehyde or ketone 2,4dinitrophenylhydrazone is formed
R2C=O + (NO2)2C6H3NHNH2 ==>
(NO2)2C6H3NHN=CR2 + H2O

Note
(1) Test (b)(i) and (ii) can be
used to distinguish aldehydes
(reaction) and ketones (no
reaction).

(b)(i) warm a few drops of the

compound with Tollens'
reagent [ammoniacal silver
(2) Aromatic aldehydes do
NOT give a positive result with nitrate]
(b)(ii) Benedict's or Fehling's
(b)(ii) simmer with Fehling's
reagent).
or Benedicts solution [a blue
complex of Cu2+(aq) ]
(3) Reducing sugars may
also give a positive test with
(b)(i)/(ii) reagent e.g. glucose
(aldohexose) but not fructose?
(ketohexose)?

(R = H, alkyl or aryl)
This tells you its an aldehyde or ketone, but can't
distinguish them, read on below!
(b) Only the aldehyde
produces (i) A silver mirror on
the side of the test tube.

Aldehydes are stronger reducing agents than ketones and

reduce the metal ion and are oxidised in the process
i.e. RCHO + [O] ==> RCOOH

(ii) A brown or brick red ppt.

(i) reduction of silver(I) ion to silver metal
RCHO + 2Ag+ + H2O ==> RCOOH + 2Ag + 2H+
(ii) reduction of copper(II) to copper(I) i.e. the blue solution of
the Cu2+ complex changes to the brown/brick red colour of
insoluble copper(I) oxide Cu2O.
RCHO + 2Cu2+ + 2H2O ==> RCOOH + Cu2O + 4H+
With (b)(i)/(ii) no reactions with
ketones.

Halogenoalkanes
(haloalkanes) chemical test
RX where R = alkyl, X = Cl,
Br or I

(i) Warm a few drops of the

haloalkane with aqueous
ethanolic silver nitrate solution,
the ethanol increases the
solubility of the immiscible
The halide is covalently bound haloalkanes.
(CX bond), so the halogen X
cannot react with the silver ion (ii) Gently simmering a few
drops with aqueous NaOH
to form the ionic Ag+X(s)
precipitate until it is converted (may need to add ethanol to
increase solubility and
to the 'free' X ionic form. Note
reaction rate). Add dilute nitric
that aromatic halogen
acid followed by aqueous silver
compounds where the X is
nitrate solution.
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.

(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.

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(i) AgNO3 + RX ==> RNO3? + 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)
The addition of dilute nitric acid prevents the precipitation of
other silver salts or silver oxide (e.g. Ag2O forms if solution
alkaline).

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QUALITATIVE ANALYSIS TESTS for identifying organic functional groups of homologous series of molecules identification

Esters chemical test RCOOR' The ester can be reacted with

saturated ethanolic
R = H, alkyl or aryl
hydroxylamine hydrochloride +
20% methanolic KOH and
R' = alkyl or aryl
gently heated until boiling.
Then mixture acidified with 1M
There is no simple test for
HCl(aq) and FeCl3(aq) added
an ester. Usually a colourless dropwise.
liquid with a pleasant 'odour'.

Deep red or purple colour

formed. The test depends on
the formation of a hydroxamic
acid RC(=NOH)OH which
forms coloured salts with Fe3+
(aq) ion.

Iodoform test

A yellow solid is formed with

This reaction is given by the alcohol ethanol CH3CH2OH and
the smell of an antiseptic,
all alcohols with the 2ol structure CHOHCH3 and
CHI3, triiodomethane, melting

NaOH(aq) is added to a
solution of iodine in potassium
The formation of CHI3,
iodide solution until most of
triiodomethane (or old name the colour has gone. The
'iodoform'.
organic compound is warmed
with this solution.

point 119oC.

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

the aldehyde ethanal CH3CHO and all ketones with the 2

one structure RCOCH3 ('methyl k etones')
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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