Pair of Organic

compounds

ORGANIC CHEMISTRY WORKSHEET

Distinguish between the following pairs of organic compounds :
Name of the Reagent
Observations wrt
Equations where applicable.
Test
with each compound

Chlorobenzene
and
Benzyl Chloride

Silver nitrate
test

Alcoholic
AgNO3

Benzyl Chloride- Will

give white ppt of
silver chloride
Chlorobenzene-No
reaction.

CCl4 and
CHCl3

Carbylamine
Test
Iodoform Test

CHCl3 gives
offensive smelling
isocyanide gas.
CCl4 No reaction.
Iso propyl alcohol is
CH3CHOH

CH3
gives yellow ppt of
CHI3

R-NH2 + CHCl3 + 3KOH --------> RNC + 3KCl +

3H2O

n-propyl alcohol
and
Iso propyl
alcohol

Primary amine
like CH3NH2,
alcoholic
KOH/NaOH
NaOH,I2

n-propyl alcohol No
reaction
Ethanol gives yellow
ppt of CHI3

CH3CO CH3 +NaOI

CHI3 + CH3COONa
CH3CH2OH CH3CHO

Methanol and
ethanol

Ethanol and
benzyl alcohol

Iodoform Test

Iodoform Test

NaOH,I2

NaOH,I2

Methanol No
reaction
Ethanol gives yellow
ppt of CHI3
benzyl alcoholNo
reaction

Important points
benzyl chloride has
chlorine attached to
side chain, so
precipitate will be
formed . in the case of
chloro benzene no
AgCl precipitate will be
formed as the chlorine
benzene bond is strong
due to resonance...

CH3CHOH CH3CO CH3

CH3

CH3CHO + NaOI
CHI3 + HCOONa
CH3CH2OH CH3CHO
CH3CHO + NaOI
CHI3 + HCOONa

Alcohols with structure

similar to CH3CH-OH
R
R=H or alkyl group.

Acetaldehyde
and
formaldehyde

Iodoform Test

NaOH,I2

Acetaldehyde gives
yellow ppt of CHI3
Formaldehyde No
reaction

CH3CHO + NaOI
CHI3 + HCOONa

Acetaldehyde
and acetone

Tollens
Reagent Test

ammoniacal
silver nitrate
solution
(Tollens
reagent)
[Ag(NH3)2]+

Acetaldehyde- gives
shiny silver mirror
Acetone - No reaction

CH3CHO + [Ag(NH3)2]+ +OH-

CH3COONa +Ag+H2O+NH3

Benzaldehyde
and acetaldehyde

Iodoform Test

NaOH,I2

CH3CHO + NaOI
CHI3 + HCOONa

Bezaldehyde and
acetophenone

Iodoform Test

NaOH,I2

3-pentanone and
2- pentanone

Iodoform Test

NaOH,I2

Acetaldehyde gives
yellow ppt of CHI3
Benzaldehyde No
reaction
Acetophenone gives
yellow ppt of CHI3
Benzaldehyde No
reaction
2- pentanone gives
yellow ppt of CHI3
3-pentanone No
reaction

Acetophenone
and
Benzophenone

Iodoform Test

NaOH,I2

CH3CO C6H5 +NaOI

CHI3 + C6H5COONa

Phenol and
Benzoic acid

Neutral ferric
chloride test

FeCl3

Phenol and

Neutral ferric

FeCl3

Acetophenone gives
yellow ppt of CHI3
Benzophenone No
reaction
Phenol gives violet
colouration
Benzoic acid-No
reaction.
Phenol gives violet

Give positive iodoform

test.
Aldehydes and ketones
having at least one
methyl group linked to
the carbonyl carbon
atom (methyl ketones
CH3CO--)
are oxidised by NaOI
(NaOI is formed when
NaOH reacts with I2 )
Iodoform test cannot be
used as both will react .

CH3CO C6H5 +NaOI

CHI3 + C6H5COONa
CH3CO C3H7 +NaOI
CHI3 + C3H7COONa

C6H5OH + Fe+3 [ (C6H5O)3Fe]

C6H5OH + Fe+3 [ (C6H5O)3Fe]

Whenever the
compound has 2-one in
name usually iodoform
test can be used.

Whenever phenol is
given use ferric
chloride test.

Acetic acid

chloride test

Ethanol and
Acetic acid

Iodoform Test

NaOH,I2

colouration
Acetic acid-No
reaction.
Ethanol gives yellow
ppt of CHI3
Acetic acid No
reaction

Ethylamine and
Aniline

Azo dye test

Ethylamine and
Diethylamine

Hinsberg
Reagent

Phenol and
Aniline

Neutral ferric
chloride test

1-propanol and
2-methyl -2propanol

Lucas Test

NaNO2/HCl
(nitrous acid
is formed in
situ) followed
by beta
naphthol

Aniline with
NaNO2/HCl (nitrous
acid is formed in
situ) give benzene
diazoniu m chloride
which reacts with
beta naphthol to
form orange ppt of
an azo dye.
Ethylamine reacts to
form an alcohol
instead of dye.

Benzenesulph
onyl chloride
(C6H5SO2Cl) is
Hinsbergs
reagent

Ethylamine- Turbidity
is seen which
dissolves in alkali
DiethylamineTurbidity is seen
which is insoluble in
alkali
FeCl3
Phenol gives violet
colouration
Acetic acid-No
reaction.
Lucas reagent 2-methyl -2- propanol
(conc. HCl and will give turbidity
ZnCl2)
immediately.
1-propanol will not
give turbidity at room
temperature

CH3CH2OH CH3CHO
CH3CHO + NaOI
CHI3 + HCOONa
C6H5NH2 + NaNO2+ HCl
C6H5N2Cl +NaCl+H2O

C6H5SO2Cl + C2H5NH2
C6H5SO2 NH C2H5

C6H5OH + Fe+3 [ (C6H5O)3Fe]

CH3C(CH3 )OH + HCl(ZnCl2)

CH3
CH3C(CH3 )Cl

CH3

Phenol and
Cyclohexanol.

Neutral ferric
chloride test

FeCl3

Formic acid and

Acetic acid

Tollen 's
reagent test

ammoniacal
silver nitrate
solution
(Tollens
reagent)
[Ag(NH3)2]+

Phenol gives violet

colouration
Acetic acid-No
reaction.
formic acid reduces
Tollen 's reagent to
metallic silver but
acetic acid doesn 't.

C6H5OH + Fe+3 [ (C6H5O)3Fe]

HCOOH + 2[Ag(NH3)2]+ + 2OH- --->

2Ag + CO2 + 2H2O + 4NH3
CH3COOH + [Ag(NH3)2]+ ----> no
silver mirror

Formic acid is the only

acid to give + test for
tollens n fehlings