Chemistry : Organic chemistry

Join Telegram: @NEETxNOAH

ORGANIC CHEMISTRY

DETECTION OF EXTRA ELEMENTS (NITROGEN, SULPHUR AND HALOGEN) IN ORGANIC COMPOUNDS

• Nitrogen, sulphur and halogens present in an organic compound are detected by Lassaigne's test.
• Organic compounds are fused with dry sodium in fusion tube and fused mass after extraction with water is
boiled and filtered, the filtrate is called sodium fusion extract
Preparation of Lassaigne's Extract
To prepare Lassaigne's extract of the compound take a small, dry piece of sodium in an ignition tube, then
put a little of given organic compound over sodium. Heat ignition tube first gently to fuse sodium then
strongly, to red-hot. Drop the red-hot tube in about 10-15 ml water containing dish or hard glass boiling test-
tube. Crush the contents in water, boil and filter. The filtrate is Lassaigne's extract.
• During preparation of sodium fusion extract covalent compound is converted into ionic compound.
• The following reactions takes place

Na + C + N ⎯⎯ → NaCN

2Na + S ⎯⎯ → Na2S

2Na + X2 ⎯⎯ → 2NaX (X = Cl, Br or I)

Test for Nitrogen

For the detection of nitrogen take 2 ml sodium extract, add a drop of NaOH and 0-5 ml freshly prepared
FeSO4 solution and boil. Cool and add dil. H2SO4 and few drops of ferric chloride solution. If a blue colour
(prussian blue) or precipitate is obtained. The presence of nitrogen is confirmed.
(i) Na + C + N → NaCN
(ii) FeSO4 + 2NaOH → Fe(OH)2 + Na2SO4
(iii) Fe(OH)2 + 2NaCN → Fe(CN)2 + 2NaOH
(iv) Fe(CN)2 + 4NaCN → Na4[Fe(CN)6]
sodium ferrocyanide
(v) 3Na4[Fe(CN)6] + 4FeCl3 → Fe4[Fe(CN)6]3 + 12NaCl
Prussian blue
or
3Na4[Fe(CN)6] + 2Fe2(SO4)3 → Fe4[Fe(CN)6]3 + 6Na2S04.
• This test fails in case of diazo compounds.
• If the amount of nitrogen present is less, then Prussian blue is present in collaidal form and the solution looks
green.

Test for Sulphur

(a) Sodium fusion extract is acidified with acetic acid and lead acetate is added to it, a black precipitate
of lead sulphide is formed, which indicates presence of sulphur.
Na2S + (CH3COO)2Pb ⎯→ PbS + 2CH3COONa
black
(b) Sodium fusion extract is treated with freshly prepared sodium nitroprusside, appearance of violet
colour (purple) indicates presence of sulphur.
Na2S + Na2[Fe(CN)5NO] ⎯→ Na4[Fe(CN)5NOS]
(sodium nitro prusside) (violet)
Join Telegram: @NEETxNOAH

[ 46 ] www.allen.in  Digital

Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
• In case both nitrogen and sulphur are present in an organic compound sodium thiocyanate is formed, which
gives blood red colour with neutral FeCl3 solution.
Na + C + N + S ⎯→ NaSCN
3NaSCN + FeCl3 ⎯→ Fe(SCN)3 + 3NaCl
(blood red)
(or)
Fe +3
+ SCN¯ ⎯→ [Fe(SCN)]+2
(blood red)
• If sodium fusion is carried out with excess of sodium, the thiocyanate decomposes to yield cyanide and
sulphide, these ions gives their usual tests.
NaSCN + 2Na ⎯→ NaCN + Na2S
• On treating sodium fusion extract with sodium nitroprusside, appearance of a violet colour further indicates
the presence of sulphur.
S2– + [Fe(CN)5NO]2– ⎯→ [Fe(CN)5NOS]4–
Violet

Test for presence of N and S both

Take about 2-3 ml of sodium fusion extract and add FeCl3 solution. Appearance of blood-red colour
confirms the presence of nitrogen and sulphur both.
3NaCNS(aq) + FeCI3 ⎯→ Fe(CNS)3 + 3NaCl
blood-red colour

Test for Halogens

• Sodium fusion extract is acidified with nitric acid and then treated with silver nitrate solution.
(i) White precipitate, soluble in ammonium hydroxide indicates presence of chlorine.
NaCl + AgNO3 ⎯→ AgCl + NaNO3
(white ppt)
AgCl + 2NH4OH ⎯→ [Ag(NH3)2]Cl + 2H2O
(soluble complex)
(ii) Yellowish precipitate, sparingly soluble in ammonium hydroxide indicates presence of bromine.
NaBr + AgNO3 ⎯→ AgBr + NaNO3
(yellowish ppt)
(iii) Yellow precipitate, insoluble in ammonium hydroxide indicates presence of Iodine.
Nal + AgNO3 ⎯→ Agl + NaNO3
yellow
precipitate
• Nitrogen and sulphur are also present in the compound, the sodium fusion extract is boiled with
concentrated nitric acid to decompose sodium cyanide & sodium sulphide formed during Lassaigne's test,
otherwise they interfere with silver nitrate test for halogens.
NaCN + HNO3 ⎯→ NaNO3 + HCN
Na2S + 2HNO3 ⎯→ 2NaNO3 + H2S
• If NaCN and Na2S are not decomposed, then white and black precipitates of AgCN and Ag 2S are formed
respectively with silver nitrate solution.

Join Telegram: @NEETxNOAH

 Digital www.allen.in [ 47 ]

 Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
ELEMENTAL ANALYSIS CHART
Lassaigne method (Detection of Elements)
Element Sodium Extract (S.E.) Confirmed Test Reactions
Nitrogen Na+C+N ⎯⎯ 
→ NaCN S.E.+FeSO4+NaOH, FeSO4+2NaOH→Fe(OH)2+Na2SO4
(S.E.) boil and cool,+FeCl3+ Fe(OH)2+6NaCN→Na4[Fe(CN)6]+2NaOH
conc. HCl Blue or green 3Na4[Fe(CN)6]+4FeCl3
colour
⎯⎯→
HCl
Fe4[FeCN]6]3+12NaCl
Prussian blue
Sulphur 2Na+S ⎯⎯ → Na2S (S.E.) (i) S.E.+ sodium nitro
 (i) Na2S+Na2[Fe(CN)5NO]→Na4[Fe(CN)4NOS]
prusside (A) (A) deep violet
A deep violet colour, (ii) Na2S+(CH3COO)2Pb ⎯⎯⎯⎯
3
→
CH COOH

(ii) S.E.+CH3COOH
PbS + 2CH3COONa
+ (CH3COO)2 Pb
black ppt.
A black ppt.
S.E. + HNO3 + AgNO3
Halogen 
Na+Cl ⎯⎯ → NaCl (S.E.) (i) White ppt. soluble in NaX + AgNO3 ⎯⎯⎯
3
→ AgX 
HNO

aq. NH3 confirms Cl ppt

(ii) Yellow ppt partially
soluble in aq. NH3
AgCl+ 2NH (aq) ⎯→[Ag(NH ) ]Cl
confirm Br 3 3 2
(iii) Yellow ppt insoluble white ppt soluble
in aq NH3 confirms I
Nitrogen Na+C+N+S ⎯⎯

→ As in test for nitrogen; NaSCN + FeCl3 → [Fe(SCN)]Cl2 + NaCl
and sulphur NaSCN(S.E.) instead of green or blue blood red colour
together colour, blood red Thiocyanato-s-iron
coloration confirms (III)chloride

presence of N and S
both

Detection of the Functional Groups Present in Organic Compounds

Physical Examination of The Compound
For an organic compound the following physical properties are observed :
(i) Physical state, (ii) Colour and (iii) Odour (smell) (iv) Effervescence
1. Test of unsaturation
• Alkene and alkyne give this test.
• Alkane and Benzene does not give this test.
(a) Bromine test
Br

e.g. CH2 = CH2 + Br2 ⎯⎯⎯⎯⎯CCl4

Reddish brown
→ CH2 – CH2

Br
olo r less
OR
Br Br
CH  CH + Br2 ⎯⎯⎯⎯⎯CCl4
Reddish brown
→ CH – CH

Br Br
olo r less
Join Telegram: @NEETxNOAH

[ 48 ] www.allen.in  Digital

Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
(b) Baeye’s reagent test ( old dil te KMnO4)
e.g. CH2 = CH2 + dil. KMnO 4 → CH2 – CH2
pink/ voilet

OH OH
olo r less
OR
–C=C – + dil. KMnO 4 → – C – C –
pink/ voilet

O O
olo r less

2. Test of 1-Alkyne and other alkyne

(a) Rea tion with a H2

e.g. R–C  + a H2 → R–CC a + H

ngent smell

b t R–CC–R + a H2 → o rea tion

(b) Rea tion with Tollen’s reagent

e.g. R–C  + Ag O + H4–OH → R–CCAg

hite t
b t R–CC–R + Tollen’s reagent → X
( ) Rea tion with Ammoni al C 2Cl2

e.g. R–C  + C 2Cl2 + H4–OH → R–CCC

Red t
all above test (a, b, ) is not given by alkane, alkene and benzene also.

3. Aliphatic or Aromatic Test

Smoky flame → Aromatic in nature
Non-smoky flame → Aliphatic in nature

4. Test for Carboxylic acids

The first member is formic acid (HCOOH) which is different from other members of this series. But the
following test are given by formic acid also :
– Litm s Test
– aHCO
– Ester test – sweet smell of ester,
(i) Litmus test : Turns blue litmus to red. This test is also given by phenol.
(ii) Sodium bicarbonate test : A brisk effervescence is given and CO 2 gas is evolved. This is not given by
phenols.
Rea tion of aHCO with arboxyli a id gives efferves en e of CO2. This test is not given by
h – OH ( henol)
R – COOH + aHCO → R COO a + CO2 + H2O
b t h – OH + aHCO → o rea tion.
(iii) Esterification test : A small quantity of the given organic compound is heated gently with 1-2 ml ethyl
alcohol and 0.5 m conc. H2SO4. A sweet fruity smell is obtained due to formation of ester. It confirms the
presence of – COOH group.
RCOOH + C2H5OH ⎯⎯⎯⎯ → RCOOC2H5 + H2O
H 2 SO 4

Join Telegram: @NEETxNOAH

 Digital www.allen.in [ 49 ]

 Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
(iv) H – COOH and R – COOH are differentiated by
(a) Tollen’s reagent (b) Fehling sol tion test
( ) Benedi t sol tion (d) H⊕/KMnO4 (e) K2Cr2O7
→ H – COOH is oxidized by above all reagents but R – COOH is not.

5. Test For Alcohols :

• Ceri Ammoni m nitrate test.
• Vi tor mayer test.
• L as test, iodoform test.
(i) Sodium Metal
1
ROH + Na ⎯⎯→ RO¯Na + + H 2 (g)
Alcohol 2
(Sodium alkoxide )

When Na-metal reacted with alcohol H2(g) evolve

(ii) Ceric Ammonium Nitrate Oxidation (CAN Test)
OR
HNO3
(NH4)2Ce(NO3)6 + ROH (NH4)2Ce(NO3)5 Ce(III)
ceric ammonium nitrate alcohol (red) colour
(yellow) decolourise

• Positive Test: Color changes from yellow to red first then to colorless solution.
Note : Phenols gives brown or black colour.
(iii) Lucas Test
• This test disting ishes 1º, 2º & º al ohol from ea h other
• It ses, anhydro s ZnCl2 in conc. HCl (lucas reagent)
(HCl + ZnCl2 )
R − OH ⎯⎯⎯⎯⎯ → R − Cl + H 2 O
• 3° alcohols give white turbidity solution immediately
• 2° al ohols give white t rbidity sol tion within 5 to 10 min tes
• 1° al ohols give white t rbidity within 30 minutes after heating.
Note : Benzyl alcohol also react immediately
(iv) Victor-Mayer Test
• This test also distinguishes 1°, 2° & 3° alcohol
Reagent : Red P + I2, NaNO2, HNO2, NaOH
1° Alcohol – Red colour
2° Alcohol – Blue colour
3° Alcohol – Colourless

6. Tests for Phenols

(i) Voilet om lex with ne tral FeCl
3−
6C6H5 + FeCl → Fe(C 6 H 5 − O)6 
Voilet

(ii) henol + hthali anhydride ⎯⎯⎯→
H
−H2O
henol hthalein
hthalein dye test
aOH

ink olo r

Join Telegram: @NEETxNOAH

[ 50 ] www.allen.in  Digital

Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH

OH OH OH OH

–H2O
H O H
C
C O
O C
C O
O
(iii) Phenols with potassium permanganate solution undergo oxidation to quinones.
OH O

3 + 4 KMnO4 3 + 4MnO2 + 4KOH + H2O

(+7) (+4)
Phenol
O
quinone
Pink colour

(iv) Bromine water

OH OH
Br Br
+ 3Br 2 + 3HBr

phenol
Br
2 ,4 ,6 -tribromophenol
(white)
• Positive Test: decolorization of bromine and gives white crystal product.
(v) Libermann’s nitroso test : (GRB test)

OH + a O2 ⎯⎯⎯⎯
H 2 SO 4
ESR
→ O OH
 
 N O 
 
ta tomerism

HO – O

Green olo r

OH
H⊕ ⊕
O – OH O
–H2O henol E R
ele tro hile

aOH
O OH alt
–H2O Bl e olo r
Red olo r
(indo henol)

Join Telegram: @NEETxNOAH

 Digital www.allen.in [ 51 ]

 Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
(vi) henol gives orange/dye with Benzene diazoni m hloride
+ – E R
Cl +
2 OH = OH
0°– 5° C
Orange dye

7. Tests For Aldehydes and Ketone

–D test, aH O test, iodoform test
– Tollen’s test, Fehling test/Benedi t
– hiffis test
(i) 2,4-Dinitrophenyl Hydrazine
NO 2 NO 2
O
pH(4 .5 –6 .0 )
+ O 2N NHNH 2 O 2N NHN=C
C

aldehyde 2 ,4 -dinitrophenylhydrazine 2 ,4 -dinitrophenylhydrazone

or ketone
• Positive Test: formation of yellow, orange or red ppt.
(ii) Sodium bisulphite (NaHSO3)
O
C + NaHSO 3 — C – OH
SO 3¯Na +
Aldehyde Sodium Bisulphite White crystalline adduct
or ketone
• Positive Test: By aldehydes and methyl ketone
(iii) Iodoform Test (For Methyl Ketones)
O O
C + 3I2 + 3NaOH CHI3 (s) + C + 3NaI + 3H 2 O
R CH 3 Iodoform
(yellow solid) R O¯Na +
methyl ketone
Sodium slat of
the carboxylic acid
• Positive Test : Yellow ppt for methyl ketones
• Some compounds that can be easily oxidized to methyl ketones give also positive results
• The principal types of compounds that give a positive test:
OH O
CH + I2 + 2NaOH C + 2NaI + 2H 2 O
R CH 3 R CH 3
2°alcohol methyl ketone
• This test is also given by Acetaldehyde (CH3–CHO)

Tests that give positive results with aldehydes and negative results with Ketones
(i) Tollens Reagents Ag(NH3)2OH

O O
C + 2Ag(NH 3 )2 OH 2Ag(s) + C + H 2 O + 3NH 3
R H R O¯NH 4 +
Tollens reagent salt of
aldehyde
carboxylic acid
• Positive Test: Formation of silver mirror (Ag) or colloidal (granular) grey or black Ag precipitate.
Join Telegram: @NEETxNOAH

[ 52 ] www.allen.in  Digital

Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
(ii) Schiff's Reagent
O
+
2 C + H 3N CH NHSO 2 H
R H 2
HO 3 S
aldehyde
schiff's reagent
(colorless)
O OH
+
H 3N CH NH—S—C—H Cl¯ + H 2 SO 3
O R
2
(violet-purple solution dye)
(iii) Benedicts solution and Fehling's Solution
• Positive Test : red ppt is obtained.
• All aldehydes give positive result except aromatic aldehydes (negative)
R CHO + CuSO4 R COO¯ + Cu2O
(Blue) Red ppt

8. Tests for Amines

(i) Nitrous Acid
Test of 1 ° and 2° Amine with H O2 (nitro s a id)
e.g. R − NH 2 + HO − N = O → R − OH + N 2 + H 2 O
1  A min e Alcohol
no colour

b t R2 − NH + HO − N = O → R 2 N − N = O
2  A min e nitroso compound
yellow oily liquid

(ii) Hinsberg Test

Hinsberg Reagent test to disting ish 1°, 2° and ° Amine.
(iii) Isocyanide Test (Carbyl amine test)
R − NH 2 + CHCl3 ⎯⎯⎯⎯
Ak. KOH
→ R − NC
1  a min e Isocyanide
pungent smell

this test is given by only 1° amine.

IMPORTANT QUESTIONS
1. Why is alcohol dried before carrying out sodium metal test ?
Ans. Because water also reacts with sodium and gives hydrogen gas with brisk effervescence.
2. Liebermann's test is used for which class of compounds?
Ans. Phenols.
3. Name a reagent used to detect carbonyl group in a compound?
Ans. (2, 4-dinitrophenyl hydrazine)
4. Name two tests which distinguish aldehydes from ketones?
Ans. Tollen's test and Fehling's test.
5. Both phenols and alcohols contain (–OH) group. How can it be ascertained that the given compound is
alcohol or phenol?
Ans. (i) Phenols are acidic in nature and turns blue litmus red whereas alcohol cannot
(ii) henol gives violet om lex with ne tral FeCl b t Al ohol not.
(iii) henol gives white rystal with Br2/H2O (E R)
(iv) henol gives orange dye with Benzene diazoni m hloride (E R)
(v) henol gives ink olo r with oxidation by air.
h – Oh + O2 → arabenzoq inone.
Join Telegram: @NEETxNOAH

 Digital www.allen.in [ 53 ]

 Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
6. What is Tollen's reagent?
Ans. Ammonical solution of silver nitrate
7. How is presence of Ketonic group in an organic compound confirmed?
Ans. Ketones give positive test with 2,4-dinitrophenyl hydrazine.
8. Dye test is given by which class of compounds?
Ans. Aromatic amines and phenols
9. How Lassaigne's solution is prepare?
Ans. Take a small piece of dry Na in a ignition tube. Add to it a small amount of given organic compound. First
heat it gently and then strongly till red hot. Now put this red hot ignition tube in a boiling tube containing
distilled water. Heat the contents of boiling tube and filter. The filtrate is Lassaigne's solution.
10. Which class of compounds turns blue litmus red ?
Ans. Carboxylic acids and phenols.
11. How will you know whether the given compound is aliphatic or aromatic ?
Ans. Burn the given compound in flame with the help of glass rod or copper wire. Compound burns with sooty
flames aromatic. Aliphatic compound burns with non-sooty blue flame
12. Name the functional group other than carboxylic group which turns blue litmus red?
Ans. Phenolic group
13. Phenols turn blue Litmus paper into red colour. Then why do not give effervescence with sodium
bicarbonate?
Ans. Because phenols are weaker acid than carbonic acid.
14. Why do aldehydes produce a shining silver deposit with Tollen's reagent?
Ans. Aldehydes reduces silver ions to metallic silver
15. hat is the se of hiff’s reagent ?
Ans. It is used to detect aldehyde group (not ketone)
16. Name the three class of compounds which give sodium metal test ?
Ans. Alcohol, Phenol, and Carboxylic acid.
17. Give simple chemical tests to distinguish between propanal and propanone.
Ans. (a) Propanal reduces Tollen's reagent, fehling solution, benedict solution but propanone (ketone) does not
reduces.
(b) Iodoform test :
Propanone CH3–C–CH3 gives iodoform test but propanal (CH3–CH2–CHO) does not.
O
18. Give simple chemical tests to distinguish between acetophenone and benzophenone.
Ans. Acetophenone and Benzophenone can be distinguished using the iodoform test.
Acetophenone gives iodoform test but benzophenone does not.
19. Give simple chemical tests to distinguish between phenol and benzoic acid.
Ans. Phenol and benzoic acid can be distinguished by ferric chloride test and NaHCO 3 test.
(a) Phenol gives voilet colour with FeCl3.
(b) Benzoic acid gives CO2 with NaHCO3 while phenol does not.
20. Give simple chemical tests to distinguish between benzoic acid and ethyl benzoate
Ans. Benzoic acid and Ethyl benzoate can be distinguished by sodium bicarbonate test.
Sodium bicarbonate test :
Benzoic acid react with NaHCO3 to produce brisk effervescence due to the evolution of CO2 gas but
ethylbenzoate does not.
21. Give simple chemical tests to distinguish between pentan-2-one and pentan-3-one
Ans. Pentan-2-one and pentan-3- one can be distinguished by iodoform test. Pentan-2-one gives iodoform test
but pentan-3-one does not.
Join Telegram: @NEETxNOAH

[ 54 ] www.allen.in  Digital

Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
22. Give simple chemical tests to distinguish between benzaldehyde and acetophenone.
Ans. Benzaldehyde and acetophenone can be distinguished by the (a) Tollen's test (b) Iodoform test.
Benzaldehyde gives Tollen's test where as acetophenone gives iodoform test.
23. Give simple chemical tests to distinguish between ethanal and propanal.
Ans. ethanal and propanal can be distinguished by iodoform test. Ethanal gives iodoform test but propanal does
not.
24. Give one chemical test to distinguish between methylamine and dimethylamine.
Ans. Methylamine gives carbylamine reaction on heating with CHCl 3 and alcoholic KOH.
Gives foul smelling (Carbyl amine)
CH3 NH2 + CHCl3 + 3KOH ⎯⎯⎯
Heat
→ CH 3 NC + 3KCl + 3H2O
Carbylamine

where as Dimethylamine does not give this reaction.

25. Give one chemical test to distinguish between secondary and tertiary amines.
Ans. Secondary amines given Hinsberg's test. Its gives insoluble substance with Hinsberg's reagent
(C6H5SO2Cl) which is not affected by base.
R 2 NH + C 6 H 5 SO 2 Cl  R 2 NSO 2 C 6 H 5 (N, N-Dialkyl benzene sulphonamide)
Sec. amine Benzene sulphonyl Insoluble in alkali
chloride

Where as tertiary amine does not react with Hinsberg's reagent.

26. Give one chemical test to distinguish between ethylamine and aniline.
Ans. Aniline gives azo dye test :
Where as aliphatic amine (ie ethylamine) does not form dye with benzene diazonium chloride.
27. Give one chemical test to distinguish between aniline and benzylamine.
Ans. Nitrous acid test :
 +
 H2O
C6 H5 CH 2 NH 2 ⎯⎯⎯
HNO2
→ C6 H 5 CH - N  NCl –  ⎯⎯⎯ → C6 H 5 CH 2 OH + N 2 + HCl
 
HCl

(gas)

+
NaNO2HCl +
NH2 273 - 278 K
NNCl–

Aniline Benzenediazonium chloride (Salt)

28. Give chemical test to distinguish between aniline and N – methylaniline.

Ans. (a) Ph − NH 2 ⎯⎯⎯⎯
CHCl3
Ak. KOH
→ Ph − NC
1  A min e Pungent smell

b t Ph − NH – CH 3 no test.
2  A min e
+
(b) Ph − NH 2 + HO − NO ⎯⎯→ Ph − N H 2 Cl
1 (BDC )

–H2O
b t h– – H + HO – =O h– – =O

CH 2° CH
yellow oily liq id

29. Give hemi al test to disting ish benzaldehyde and a etaldehyde.

Ans. (i) A etaldehyde + Fehling sol tion → Red t
B t Ph − CHO does not given this test.
(Aromatic aldehyde )


(iii) CH – CHO + I2 + aOH ⎯⎯ → CHI yellow t
b t h – CHO does not give iodoform test.
Join Telegram: @NEETxNOAH

 Digital www.allen.in [ 55 ]

 Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
PREPARATION OF ORGANIC COMPOUND
Preparations of organic compounds highlight the importance of some common organic reactions.
Preparation of commonly used compounds like aspirin-a pain killer, iodoform-a disinfectant helps the
students to know the practical problems and the method involved in the formation of compounds.

EXPERIMENT-1
Object: To prepare acetanilide from aniline.
Chemicals required : Aniline, acetic anhydride, glacial acetic acid.
Theory: When aniline is treated with acetic anhydride in presence of glacial acetic acid, acetanilide is
formed.
O
NH 2 NH–C–CH 3
O O
glacial acetic acid
+ H 3 C–C–O–C–CH 3 + CH 3 COOH
Acetic anhydride Acetic acid
Aniline Acetanilide
Prepare of Acetanilide
CH 2 −COCl
Ph − NH 2 ⎯⎯⎯⎯⎯
Pyridine
→ h– H – C – CH
O
Result: White shining crystals of acetanilide is formed
Melting point = 113°C

EXPERIMENT-2
Object : To prepare p-nitroacetanilide from acetanilide.
Chemicals required: Acetanilide, Conc. HNO3, Conc. H28SO4, and methylated spirit.
O O O
H–N–C–CH 3 H–N–C–CH 3 H–N–C–CH 3
NO 2
conc. HNO 3 + conc. H 2 SO 4
+

NO 2
p-nitro acetanilide o-nitro acetanilide
Result:
Colour = Colourless to white
Melting point = 215°C

EXPERIMENT-3
Object : Preparation of p-amino azobenzene (aniline yellow)
Chemicals required : Aniline, benzene diazonium chloride, conc. HCl, etc,
Theory : Benzene diazonium chloride reacts with aniline in acidic medium at slightly high temperature
(30 to 35°C) to form aniline yellow.
3 0 – 35 °C
N = N — Cl + H NH 2 N=N NH 2 + HCl
H+
Benzene diazonium chloride Aniline p-amino azobenzene (aniline yellow)

Result : Yellow coloured crystals formed are of aniline yellow.

Melting point = –6°C

Join Telegram: @NEETxNOAH

[ 56 ] www.allen.in  Digital

Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
IMPORTANT QUESTIONS
1. What is acetylation?
Ans. The process of removal of –OH, –NH2, or >NH group by acetyl group is known as acetylation.
2. Name some acetylating agents.
Ans. Acetyl chloride, acetic anhydride.
3. What is oleum ?
Ans. Fuming H2SO4 is called oleum. Its formula is H2S2O7.
4. Why direct nitration of aniline is not done?
Ans. Because NH2 group of aniline gets oxidized?
5. What is coupling reaction?
Ans. Reaction in which arene diazonium salts react with phenol, aniline, etc. to form coloured dyes called azo dye
is callled coupling reaction.
6. What is the formula of benzene diazonium chloride.
+ –
N= NCl

Ans. C 6 H 5 –N= N–Cl or

7. Write chemical name and formula of aniline yellow.

Ans. Name-p-Aminoazobenzene.
Formula :
N=N NH 2

Join Telegram: @NEETxNOAH

 Digital www.allen.in [ 57 ]

 Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
EXERCISE : MULTIPLE CHOICE QUESTIONS
1. Match the following Column I with Column II and CHO
CHO
choose the correct option from the codes given C2H 5
below. (1) (2)

Column-I Column-II C2H 5

(Distinguish) (By reagent) O
A. Methanol and diethyl 1 Lucas CHO
C
ether reagent
.
(3) CH 3 (4)
B. Methanol and ethanol 2 Sodium
CH 3 C2H5
metal
.
5. Hinsberg reagent is ...I... which reacts with ...II...
C. Phenol and 3 Iodoform
amines to form sulphonamides.
cyclohexanol test.
Identify I and II for the given statement and
D. n-propyl alcohol and 4 Ferric choose the correct option.
tert-butylalcohol chloride
.
(1) I→ SO 2 Cl ; II→ primary and secondary
Codes
A B C D
(1) 2 4 3 1
(2) I→ SO 2 Cl ;II → secondary and tertiary
(2) 2 3 4 1
(3) 2 3 1 4
(3) I→ CH 2 Cl ;II → primary and secondary
(4) 3 2 1 4
2. Assertion (A) A bright silver mirror is produced (4) I→ CH 2 Cl ;II → secondary and tertiary
during the warming of an aldehyde with freshly
6. Assertion (A) : N-ethylbenzene sulphonamide is
prepared ammoniacal silver nitrate solution.
soluble in alkali medium.
Reason (R) A bright silver mirror is produced
due to the formation of silver metal. Reason (R) : The hydrogen attached to nitrogen
(1) Both (A) and (R) are true and (R) is the in sulphonamide is strongly acidic due to the
correct explanation of (A). presence of strong electron withdrawing sulphonyl

(2) Both (A) and (R) are true and (R) is NOT the group.

correct explanation of (A). (1) Both (A) and (R) are true and (R) is the

(3) (A) is true but (R) is false. correct explanation of (A).

(4) (A) is false but (R) is true. (2) Both (A) and (R) are true and (R) is NOT the

3. Tollen's test occur in correct explanation of (A).

(1) Acidic medium (3) (A) is true but (R) is false.
(2) Alkaline medium (4) (A) is false but (R) is true.
(3) Neutral medium 7. HCHO and HCOOH are distinguished by treating
(4) Both acidic and alkaline medium with
4. An aromatic compound 'X' with molecular (1) Tollens reagent (2) NaHCO3
formula C9H10O gives the following chemical tests (3) Fehling's solution (4) Benedict solution
I. Forms 2, 4-DNP derivative, 8. Formaldehyde can not be distinguished from
II. Reduces Tollen's reagent,
acetaldehyde by
III. Undergoes Cannizzaro reaction and
(1) Fehling's solution
IV. On vigorous oxidation 1,2-benzene
(2) Schiff's reagent
dicarboxylic acid is obatined.
X is :- (3) Ammonia
(4) Ammonical AgNO3
Join Telegram: @NEETxNOAH

[ 58 ] www.allen.in  Digital

Chemistry : Organic chemistry
Join Telegram: @NEETxNOAH
9. Acetone reacts with iodine (I2) to from iodoform in 18. Which of the following reactions take place in
the presence of Lassaigne's test for the detection of N present in
(1) CaCO3 (2) NaOH an organic compound
(3) CaO (4) MgCO3 (1) Na + C + N → NaCN
10. What is the IUPAC name of acetanilide (2) FeSO4 + NaCN → Na4[Fe(CN)6]
(3) 2Na4[Fe(CN)6] + Fe2(SO4)3
(1) N-phenylethanamide
→ 2NaFeIII[FeII(CN)6] + 3Na2SO4
(2) Pent-2-ene
(4) All of thease
(3) Pent-1-ene-4-yne
19. Which compound burn sooty flame ?
(4) Hexa-1, 3-dien-5-yne (1) R–OH (2) R–CHO
11. What is the function of zinc dust in synthesising OH
acetanilide? R
(3) C=O (4)
(1) Prevent the reduction
R
(2) Prevent the hydrolysis
(3) Prevent the oxidation 20. Which compound burn non sooty flame ?
NH 2
(4) Prevent the dissolution
12. Which of the following is a basic dyes (1) R–OH (2)
(1) Cango red (2) Aniline yellow
(3) Alizarin (4) Indigo OH
13. Which of the following compounds will gives (3) (4)
Lassaigne's test for nitrogen.
(1) NH2NH2 (2) NH4Cl (3) NaCN (4) NaNO3 21. Which functional group is present in aspirin.
14. An organic compound containing N, S and O as
extra elements is fused with sodium metal and (1) –CHO (2) C=O
then extracted with water. The species which is
not present in the sodium extract is (3) (4) –COOH
C – OH
(1) CN (2) CNS (3) NO 3 (4) S2–
15. The red colour product in the Lassaigne's extract 22. Liebermann's nitro test is used for which class of
is due to formation of compounds
(1) Phenol (2) Ketone
(1) Fe ( SCN )2  (2) Fe ( CNS )
−1 2+
(3) Ether (4) Carboxlic acid
(3) Fe(CN)3 (4) Fe(CNS)3 23. What is tollen's reagent ?
16. Which of the following has violet colour? (1) NH4 (2) AgNO3
(3) AgNO3 + NH4OH (4) CuSO4
(1) Na 2 Fe ( CN )5 NO 
24. Dye test is given by which class of compounds
(2) Na 4  Fe ( CN )5 (NO)S  (1) Carboxlic (2) Aliphatic Amine
(3) NaCNS (3) Aromatic amine (4) OH
(4) None of these 25. Which compound turns blue litmus to red ?
17. Which of the following cannot be tested in an (1) R–OH (2) R–CHO
R
organic compound by using Lassaigne's method. (3) C=O (4) Phenol
(1) N (2) F (3) S (4) P R

ANSWER KEY
Que . 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans . 2 1 2 1 1 1 2 3 2 1 3 2 3 3 4
Que . 16 17 18 19 20 21 22 23 24 25
Ans . 2 2 4 4 1 4 1 3 3 4

Join Telegram: @NEETxNOAH

 Digital www.allen.in [ 59 ]