A] Dyes: Classification on the basis of structure and mode of application, Preparation and uses of Methyl orange, Crystal violet, Phenolphthalein , Alizarin and Indigo. B) DRUGS: Analgesic and antipyretics: Synthesis and uses of phenylbutazone. Sulpha drugs: Synthesis and uses of sulphanilamide and sulphadiazine. Antimalarials: Synthesis of chloroquine from 4,7-dichloroquinoline and its uses. C] Pesticides: Insecticides: Synthesis and uses of malathion. Herbicides: Synthesis and uses of 2,4-dichloro phenoxy acetic acid (2,4-D). Fungicides: Synthesis and uses of thiram (tetramethyl thiuram disulphide).

1. 1
B.Sc. Final year
Sem-V Students
on
Dyes, Drugs &
Pesticides
by
Dr Pramod R Padole

2. 2

4. LOGO
Unit - IV

6. A) Dyes:

7. B) Drugs:

8. C) Pesticides:
Depression
उद्देश्यहीन, उत्साहहीन, ईश्वरववहीन जीवन मौत की ओर ले जाता है

10. Organic Chemisrtry
Unit-IV
A) Dyes
B) Drugs
C)Pesticides

11. Contents :
By Dr. Pramod R. Padole
Preparation and uses of Alizarin
Preparation and uses of Phenolphthalein
Preparation and uses of Crystal violet
Preparation and uses of Methyl orange
Classification on the basis of structure and mode of application
A)Dyes:
Preparation and uses of Indigo

12. Unit- IV B) Drugs:
By Dr. Pramod R. Padole
1
Analgesic and
antipyretics:
Synthesis and
uses of
Phenylbutazone
2
Sulpha drugs:
5
Synthesis and
uses of
Sulphanilamide
&
Sulphadiazine
3
Antimalarials:
Synthesis of
chloroquine from
4,7-
dichloroquinoline
and its uses.

13. C) Pesticides:
A
INSECTICIDES:
B
HERBICIDES:
C
FUNGICIDES:
D
RODENTICIDES:
Pesticides
I H F R

14. LOGO
Unit-IV A) Dyes:
When the first man picked the first berry,
dyes were discovered.
Dyes make the world more colourful.
Dyes make the world more colorful.
But all coloured compounds are not dye.

15. By Dr Pramod R Padole
Dyes:
 Defination:
(1) Dyes are coloured organic compounds (substances) or
mixture that are used for imparting (capable of being)
colour to various substrates, such as paper, leather, fur, hair,
drugs, cosmetics, waxes, greases, plastics and textile
materials.
OR
(2) A Dye is a coloured compound which is capable of
being fixed to a fabric.
OR
(3) Dye is defined as a coloured substance which when
applied to the fibres gives it a permanent colour.

Q.1) What are dyes? (S-10 & S-14, 1-2 Mark)
Q.2) What is a dye? What are the conditions for a compound to act as a dye?

16. Dyes:
 Dye is resistant to action of water, soap and
light.
 Many natural dyes, both of animal and plant
origins have been known from a long time.
 But now days, all dyes are synthesized
practically. Synthetic dyes are superior to
natural dyes in many respects. They are deeper
and uniform in quality and most of them are
quite stable to washing and light.

17. Dr Pramod R Padole
Two important conditions for a
coloured compound to act as a dye are-
Presence of
Chromophore
Dye
Condition
But all coloured compounds are not dye.
Presence of
Auxochromes

18. By Dr Pramod R Padole
(i) Chromophore:
[Greek: Chromo= colour, Phores= bearer]
Defination: The unsaturated group which gives colour to
the compound (substance) by absorbing UV-Visible
light (radiation) is called as chromophore.
 It contains π-electron.
 Examples: Some important chromophores are ;
 >C=C<, -CΞC-, ─N═O (nitroso), ─NO2, ─N═N- (azo),
>C═O, >C═S (Thio), ─C≡N, etc.
 The compounds bearing (containing) chromophores
are known as chromogens.
Q.1) Define the terms: (W-09, 2 Mark)
(i) Chromophore & (ii) Auxochrome
Q.2) What are chromogens?
Q.3) A chromogen without auxochrome can never act as a dye.
(W-15, W-18 & S-19, ½ Mark)
Q.4) The compounds bearing chromophores are known as …… ( Ans: chromogens)

19. Dr Pramod R Padole
Auxochrome: (increases intensity of colour & λmax of chromophore)
 [Greek: Auxanein= to increase; Chromo= colour]
Defination:
 The saturated group containing lone pair of
electrons which increases intensity of colour and
wavelength of maximum absorption (λmax) of
chromophore is called as auxochrome.
 It contains non-bonding electron (lone-pair electrons).
 e.g. : -OH, -NH2, -X, etc. are auxochrome.
 Dye must be attached to fibres by means of stable chemical
bonds. Those bonds are formed by some acidic or basic
groups. Such groups are known as auxochromes.

20. Dr Pramod R Padole
Auxochrome: (increases intensity of colour & λmax of chromophore)
 ─OH, ─COOH, ─SO3H (acidic)
 ─NH2, ─NHR, ─NR2 (basic)
 A chromogen without auxochrome can never
act as a dye. (W-15, W-18 & S-19, ½ Mark)
Auxochrome
N=N N=N OH
Azobenzne
(Red)
p-hydroxyazobenzene
(Bright red)
Chromophore
Auxochrome

21. Classification of Dyes:
A Classification of dyes on the
basis of structure
B
Classification of dyes on the
basis of mode of application
C
Dyes can be classified into acidic
and basic depending upon the
nature of the auxochrome present

22. Classification of dyes on the basis of
structure:
Structure
Nitro and Nitroso dyes
Miscellaneous dyes
Azo dyes
(e.g. Methyl orange)
Triphenyl methane dyes
(e.g. Crystal violet)
Anthraquinone dyes
(e.g. Alizarin)
Indigoid (e.g. Indigo)
and Thioindigoid dyes
Depending upon the type of chromophore present in their
structures, the dyes are classified into following main types.
Phthalein dyes (e.g. Phenolphthalein)

23. LOGO
“ Add your company slogan ”
Nitro and
Nitroso
dyes:
The -NO2 (nitro) and –N=O (nitroso)
groups are chromophores in this
class of dyes.

24. (i) Nitro and Nitroso dyes:
The -NO2 (nitro) and –N=O (nitroso) groups
are chromophores in this class of dyes.
 Examples:

25. Company
LOGO
(ii) Azo Dyes:
Q.1) What are azo dyes? (W-11, W-13, S-16, W-16 & W-17, 1 Mark)
Q.2) Explain with suitable examples of Azo dyes. (S-12, 2-4 Mark)
Q.3) –N=N- group is present in…………. (Ans: azo dye)

26. (ii) Azo Dyes:
 The azo dyes contain one or more azo (─N=N─) groups as
chromophores.
 The auxochromes present in these dyes are ─OH, ─SO3H,
─NH2, ─NR2, etc. These dyes possess a wide range of
colours ranging from yellow to orange and red.
 These are prepared in the following stages.
 The examples of the azo dyes are methyl orange, congo
red, para red, bismark brown etc.
a) Aromatic amine diazo salt
diazotization
b) Diazo salt + (Aromatic phenol or amine) Coupling
Azo dye

27. 1) Methyl Orange:
 Structure of Methyl Orange:
Q.1) Give the method of preparation and uses of methyl orange.
(W-09, W-12, S-13, S-14, W-14, S-16 & W-16, 4 Mark)
Q.2) Give the synthesis / preparation and uses of methyl orange.
(W-11, S-14, W-17, S-18, S-19 & W-19, 4 Mark)
Q.3) Draw the correct structure/ structure of methyl orange dye.
(W-12 & W-13, 2 Mark)
Q.4) Write/ Name the chromophore present in the methyl orange dye.
(S-15, 1 Mark)
Q.5) Methyl orange is an example of azo dye. (W-13, ½ Mark)
Q.6) Explain with suitable example Ingrain dyes. (W-13, 4 Mark)
Q.7) Methyl Orange is an example of: (W-17, ½ Mark)
(a) Nitroso dye (b) Phthalein dye (c) Azo dye (d) Anthroquinone dye
Q.8) The –SO3H group in Methyl Orange acts as auxochrome.
Q.9) Methyl Orange is……… (Ans: azo dye)
N N N(CH3)2
S
HO3
Methyl orange (dimethyl amino azobenzene sulphonic acid )
Acidic

28. 1) Methyl Orange:
Methyl orange is an example azo dye
containing one azo (-N=N-) group.
It contains sulphonic acid (-SO3H) group
and hence it is acidic azo dye. This -SO3H
group makes the dye more soluble and is
also used as reactive point for fixing the dye.
This -SO3H group acts as auxochrome.
The azo dyes are good examples of ingrain
dyes (on the basis of mode of application).

29. Preparation of Methyl orange :
(dimethyl amino azobenzene sulphonic acid):
Step-1) Diazotisation of sulphanilic Acid:
HO3S N H2 O N O H H Cl
0 - 50
C
Sulphanilic acid Nitrous acid Diazotisation
HO3S N N Cl
Diazotised sulphanalic acid
2 H2O
NaNO2 HCl
HNO2
HNO2 NaCl
+
0 - 5 0
C
+
NaNO2/HCl
Sodium nitrite Nitrous acid
in Ice cold
condition
or
in Ice cold
condition

30. Preparation of Methyl orange :
(dimethyl amino azobenzene sulphonic acid):
Step-2) Coupling of diazo compound (or salt)
with dimethyl aniline:
HO3S N N Cl H N
CH3
CH3
+ HCl
HO3S N N N
CH3
CH3
Dimethylamino - azobenzene sulphonic acid
(Methyl orange)
Diazotised sulphanilic acid
dimethyl aniline
Coupling
(Helianthine)
H O3S N N N
CH3
CH3
Dimethylamino - azobenzene sulphonic acid
(Methyl orange)
(Helianthine)
NaO3S N N N
CH3
CH3
Dimethylamino - azobenzene sulphonic acid [Sodium salt]
(Methyl orange)
NaOH
HO-Na
+ H2O
It is generally isolated as the sodium salt, which is used as dyeing.

31. By Dr Pramod R Padole
Properties and uses:
1 2 3 4
Methyl orange is
soluble in water
because it
contains acidic
-SO3H group.
It is resist to light
and soap.
Hence it is used
as a dye.
It is
generally
isolated as
the
sodium
salt,
which is
used as
dyeing.
It
imparts
orange
colour
to
wool
and
silk.
It is used as
an indicator
in acid-base
titration
(pH range of
methyl
orange =
3.1 - 4.5).
5
Methyl
orange is
yellow in
alkaline
solution
(base) and
red in
acid
solution.

32. Why?
O3S N N N
CH3
CH3
H
O3S N N N
CH3
CH3
H
Methyl orange (Yellow in base)
Methyl orange (Red in acid)
Acid
Base
Azo chromophore
p-Quinoid chromophore
Methyl orange is yellow in alkaline solution (base) and
red in acid solution.
It is generally
isolated as the
sodium salt, which
is used as dyeing.

33. Company
LOGO
(iii) Triphenyl Methane Dyes
(Triaryl Methane):

34. www.themegallery.com
(iii) Triphenyl Methane Dyes
(Triaryl Methane):
 Tri-phenyl-methane dyes can be identified by
common structural representation shown below:
 The central C-atom is joined to three aromatic
rings, one of which is p-quinoid ring and two
are benzene rings.
 In these dyes, quinoid group is the
chromophore. The examples of this class of
dyes are crystal violet, malachite green, rosaniline (magenta),
para-rosaniline, methyl violet, aniline blue, etc.
c
Triphenyl - methane skeleton
quinoid as a
chromophore

35. Crystal Violet:
Q.1) Give the method of preparation, properties and uses of crystal violet
dye. (S-10, S-12, W-12, S-13 & W-13, 4 Mark)
Q.2) Identify chromophore, chromogen and auxochrome in the
crystal violet dye. (W-12, 2 Mark)
Q.3) Give the synthesis and uses of crystal violet.
Q.4) Draw the correct structure of crystal violet dye. (W-16, 2 Mark)
Q.5) Write/ Name the chromophore present in the crystal violet dye.
Q.6) Crystal violet is an example of triphenyl methane dye.
(W-12, ½ Mark)
Q.7) Which type of a dye is Crystal Violet?
Q.8) The crystal violet dye is used in the manufacture of inks,
stamping pads and typewriter ribbons.
Q.9) Which dye is synthesized from Michler’s ketone?
Q.10) Give the preparation of crystal violet. (W-15, 4 Mark)
Q.11) Give the preparation and uses of crystal violet. (S-17, 4 Mark)
Q.12) Give the method of preparation and properties of crystal violet dye
(W-17, 4 Mark)
Q.13) Give the structure and uses of crystal violet. (S-18, 2 Mark)

36. Preparation of Crystal Violet:
Structure of Crystal Violet:
c N(CH3)2 Cl
N
N(CH3)2
(CH3)2

37. Preparation of Crystal Violet:
Step-1) Preparation of Michler’s ketone:
When Dimethyl aniline (two
equivalents) is reacted with Carbonyl
Chloride; to form Michler’s ketone.
N(CH3)2
H
(CH3)2N H Cl C
O
Cl
N(CH3)2
C
O
(CH3)2N
Dimethyl aniline Carbonyl chloride Michler's ketone
2 HCl

38. Preparation of Crystal Violet:
Step-2) Condensation of Michler’s ketone
with dimethyl aniline:
Dimethyl
aniline
Michler's
ketone
Colour
base
Crystal
violet
HCl
Anhydrous POCl3
or AlCl3
condensation

39. www.themegallery.com Company Logo
It is
soluble in
water and
gives deep
blue
colour.
This dye forms
large crystals
which are
violet in
colour. Hence
the name
Crystal violet
These dyes
have intense
colours but
these colours
fade rapidly in
light, so these
are not useful in
textile industry
Properties of Crystal Violet:
First Second Third

40. pramodpadole@gmail.com By Dr Pramod R Padole
Uses of Crystal Violet:
First Second Third Fourth
In the
manufacture
of inks,
stamping
pads and
typewriter
ribbons.
It is also used
as an indicator
to find out H+
ion
concentration
of solution.
Gentian violet
(a combination of
crystal violet &
methyl violet)
is used as an
antiseptic for
certain skin
diseases like burn,
ulcers and also
used for washing
the wounds.
Used in
making
pencils
and
colouring
papers.

41. Company
LOGO
(iv) Phthaleins Dyes:
formed from phthalic anhydride and phenols; in
presence of dehydrating agents like fused ZnCl2 or
conc.H2SO4.

42. LOGO
By Dr Pramod R Padole
(iv) Phthaleins Dyes:
The term phthalein is used to represent the dyes
formed from phthalic anhydride and phenols; in
presence of dehydrating agents like fused ZnCl2 or
conc.H2SO4.
The characteristic chromophoric group present in
these dyes is triphenyl-methane structure.
 For example, Phenolphthalein

43. LOGO
By Dr Pramod R Padole
Preparation of Phenolphthalein:
 Phenolphthalein:
Q.1) Which are the indicators used in acid-alkali titrations?
Q.2) Which dye is formed by the reaction of phenol and phthalic
anhydride?
Q.3) Phthalic anhydride and Phenol are the two starting materials to
synthesize Phenolphthalein dye.
Q.4) Phenolphthalein is synthesized from …………. ( Ans: Phenol &
phthalic anhydride)
Q.5) Give the preparation and uses of Phenolphthalein. (W-15, 4 Mark)
Q.6) Give the structure and uses of Phenolphthalein. (S-18, 2 Mark)
Phenolphthalein is formed from phthalic anhydride
and phenols; in presence of dehydrating agents
like fused ZnCl2 or conc.H2SO4.

44. LOGO
By Dr Pramod R Padole
Preparation of Phenolphthalein:
 When phenol (2 equivalents) is heated with phthalic
anhydride in presence of ZnCl2 or con.H2SO4 at
120oC, undergoes condensation; to form
Phenolphthalein.
OH
H
OH
H
C
O
C
O
O
Phthalic anhydride
Conc. H2SO4
+ H2O
C
C
O
O
OH
HO
Phenolphthalein
(Colourless crystalline solid)
or ZnCl2
at 120o
C
Condensation
(393 K)
Phenol

45. LOGO
By Dr Pramod R Padole
It is used as an
acid-base
indicator than a
dye.
In alkali it gives a
pink colour and in
acid it is
colourless.
Phenolphthalein
is a
colourless
crystalline solid
Phenolphthalein
is insoluble in
water but
soluble in
alcohol and
alkali; to form
deep red
solutions.
Uses of Phenolphthalein :
First Second Third

46. LOGO
By Dr Pramod R Padole
It is used as an acid-base indicator than a dye.
In alkali it gives a pink colour and in acid it is
colourless.
Uses of Phenolphthalein :
(This is due to the formation of a disodium salt, the ion
of which is coloured because of resonance.
When excess of strong alkali is added, the solution of
phenolphthalein becomes colourless.
This is attributed to the formation of a trisodium salt,
the ion of which is colourless because of loss of resonance
and quinoid structure.)

47. 47
B.Sc. Final year
MEB Students
for
Today’s
Chemistry Lecture
by
Dr Pramod R Padole

49. Company
LOGO
(v) Indigoid Dyes:
and
thioindigoid Dyes:
Indigo is obtained naturally from plants of indigofera group .
Indigofera is a large genus of over 750 species of
flowering plants belonging to the pea family

50. Company name
Preparation of Indigo
by Heumann’s Synthesis (in 1896):
Indigoid dyes contain the group as a
carbonyl chromophore.
Indigo is obtained naturally from plants of
indigofera group .
 Structure
Q.1) What are vat dyes? Explain with suitable example. (S-11, 4 Mark)
Q.2) Which starting compound is used to synthesize Indigo dye?
Q.3) Indigo is an example of a ………..dye.

51. LOGO
www.themegallery.com
Indigoid and thioindigoid Dyes:
Preparation of Indigo:
When anthranilic acid and chloroacetic acid
(Cl-CH2COOH) is undergoes condensation; to form
N-phenylglycine-o-carboxylic acid, which is fused
with sodium hydroxide ( NaOH or KOH) and
sodamide; to form unstable indoxylic acid, which
undergoes further decarboxylation (-CO2); to form
indoxyl.
Oxidation of indoxyl (2 molecules) by air; to form
Indigo dye.
Indigo is as a dye for cotton yarn, which is mainly for the
production of denim cloth for blue jeans.
Preparation of Indigo by Heumann’s Synthesis (in 1896):.

52. Company name
Preparation of Indigo
by Heumann’s Synthesis (in 1896):
 When anthranilic acid and chloroacetic acid (Cl-CH2COOH) is
undergoes condensation; to form N-phenylglycine-o-carboxylic acid,
which is fused with sodium hydroxide ( NaOH or KOH) and sodamide; to
form unstable indoxylic acid, which undergoes further
decarboxylation (-CO2); to form indoxyl.
 Oxidation of indoxyl (2 molecules) by air; to form Indigo dye.
Indigo is a good example of a vat dye (on the basis of mode of application).

53. Company name
Properties & Uses of Indigo:
Indigo is a dark-blue
Crystalline compound,
Insoluble in water
Indigo is as a dye for cotton yarn,
Which is mainly for the production
Of denim cloth for blue jeans.
It is used for dyeing cotton
By vat process.
Uses of
Indigo

54. Company name
Thioindigo:
 Thioindigo is similar to indigo but differs only in one
respect that in place of two ─NH groups there are
two ‘S’ -atoms.
 Thioindigo is used to dye cotton, wool and polyester.
 For example, Thioindigo dye.
S
O
S
O
Thioindigo

55. LOGO
(vi) Anthraquinone Dyes:
These include hydroxy
or amino derivatives of
anthraquinone
para quinoid chromophore is present in these anthracene-type dyes
in which p-quinoid group is used to two other benzene rings

56. LOGO
Alizarin:
Q.1) Give the preparation / synthesis and uses of Alizarin. (W-09, S-16, S-17,W-18 & W-19, 4 Mark)
Q.2) Write the names of chromophore present in the Alizarin. (W-11, S-14 & W-14, 1-2 Mark)
Q.3) Draw the correct structure of the Alizarin. (W-12 , S-14 & W-16, 1-2 Mark)
Q.4) Explain with suitable example of Anthraquinone dye ( e.g. Alizarin dye). (S-12, 4 Mark)
Q.5) Alizarin is an example of Anthraquinone / mordant dye.(mode of their application)(S-16, ½ Mark)
Q.6) Alizarin is a anthroquinone dye.
Q.7) Alizarin is : (W-18 & W-19, ½ Mark)
(a) Direct dye (b) Ingrain dye (c) mordant dye (d) Vat dye
(vi) Anthraquinone Dyes:

57. pramodpadole@gmail.com By Dr. P. R. Padole
Alizarin is an example of
Anthraquinone dye.
It is 1,2-dihydroxyanthraquinone.
 Alizarin name derives from the fact
that it was first obtained from the red
roots of the madder plant having
yelllow flowers (Fr. Alizari, madder).
 Eurasian herb having small yellow flowers and
red roots formerly an important source of the
dye.

58. Preparation of Alizarin:
Step-1) Preparation of Anthraquinone
from Phthalic anhydride:
 When phthalic anhydride is treated with benzene in the presence
of AlCl3; to form o-benzoylbenzoic acid, which is further treated
with con. H2SO4; to form anthraquinone.
C
C
O
O
O
AlCl3
Phthalic Anhydride
Benzene
Friedel crafts
reaction
C
O
o - Benzoyl Benzoic Acid
H
O
C-OH
H
/Conc. H2SO4
Dehydration
(-H2O)
O
O
Anthraqinone

59. Fuming sulfuric acid is a mixture of pyrosulphuric
acid, H 2 S 2 O 7, and other condensed acids, made by
dissolving sulphur trioxide in concentrated sulphuric acid.
Also called: oleum, Nordhausen acid
Q.1) What is the difference between
sulfuric acid and fuming sulfuric acid?
 The key difference between oleum
and sulfuric acid is that the oleum is sulfur
trioxide in sulfuric acid whereas the sulfuric
acid is an inorganic acid having the chemical
formula H2SO4. We call oleum as “fuming
sulfuric acid” as well. ...
 Sulfuric acid, on the other hand, is a syrupy
liquid, which is highly water soluble.

60. Preparation of Alizarin:
Step-2) Sulphonation of anthraquinone
by fuming H2SO4 at 160-180oC :
 When anthraquinone is heated with fuming sulphuric acid (H2SO4) at
160-180oC; to form anthraquinone-2-sulphonic acid.
O
O
Anthraquinone
Fuming H2SO4
at 160-1800
C
O
O
Anthraqinone-2-sulphonic acid
SO3H
H
+ HO - SO3H
+ H2O
1
2

61. Preparation of Alizarin:
Step-3) Formation of Alizarin from
Anthraquinone-2-sulphonic acid:
 When anthraquinone-2-sulphonic acid is fused with NaOH in the
presence of potassium chlorate (KClO3) at 200oC under pressure and
followed by acidification by dil. H2SO4; to form Alizarin (1,2-
dihydroxyanthraquinone)
(1) Fused with NaOH/KClO3
(2) H+
(acidificatin)
O
O
SO3H
O
O
OH
OH
Alizarin
Anthraquinone-2-sulphonic acid
(1,2-dihydroxyanthraquinone)
Heat at 200o
C &
Under pressure
H

62. (1) Fused with NaOH/KClO3
(2) H+
(acidificatin)
O
O
SO3H
O
O
OH
OH
Alizarin
Anthraquinone-2-sulphonic acid
(1,2-dihydroxyanthraquinone)
Heat at 200o
C &
Under pressure
H
O
O
SO3H
Anthraquinone-2-sulphonic acid
H
+ NaOH
+ Na-OH
Step-1)
O
ONa
SO3H
H
OH
- SO3H + Na = NaHSO3
O
O
ONa
H
K O -Cl =O
O
+
O
K O -Cl =O
O
O
ONa
H
O
O Cl =O
OH
O
O Na
O ClO2
O
O
OH
OH
Alizarin
(1,2-dihydroxyanthraquinone)
H OH
H OH
H2O:
;
proton transfer
Acid Hydrolysis
H / H2O
Step-2)
Step-3
Step-4
Step-5

63. Properties & Uses of Alizarin:
Alizarin forms ruby red crystals
1
Sparingly soluble in water, soluble in alcohol and ether
2
It is sublimes on heating
3
Alizarin is used to dye cotton and wool
4
It is used as purgative (mild cathartic) in medicine
5
It is used in manufacture of printing inks
6

64. 64
B.Sc. Final year
MEB Students
for
Today’s
Chemistry Lecture
by
Dr Pramod R Padole

67. p,p-Dichloro-diphenyl-trichloroethane)

68. DDT Formation:
Or Preparation of p,p-dichloro,diphenyl,trichloroethane
Or Reaction with Chlorobenzene & Chloral (trichloroacetaldehyde)
DDT Formation :
When chlorobenzene(two molecules) is reacted with
chloral (trichloro-acetaldehyde) in presence of con. H2SO4;
to form p,p-dichloro,diphenyl,trichloroethane (DDT).

69. WHY DO PEOPLE USE
DRUGS?

70. RISK FACTORS
• Academic Failure (low and failing grades)
• Little commitment to school / College

71. PROTECTIVE FACTORS
• Involvement in alternative activities
• Sense of well being and self-confidence

72. PROTECTIVE FACTORS
• Positive future plans
• Healthy coping strategies to deal with stress
• Positive attitude towards learning

73. PROTECTIVE FACTORS
Negative attitude towards substance use

74. By
Dr. P. R. Padole
Department of Chemistry
Shri Shivaji Science College, Amravati.

75. Contents of Unit-IV:
Dyes:
1
Drugs:
2
Pesticides:
3
Unit Test
4

76. Do you know?
Drugs:

77. Drugs:

79. Drugs:

80. Drugs:
Q.1) What is drug? (W-13, 1-2 Mark)
Q.2) What are drugs? (W-14, 1-2 Mark)
Q.3) What are drugs? What requirements should ideal drug satisfy.
The term ‘drug’ is derived from a French word: ‘drogue’ – a dry herb.
Defination:
According to World Health Organisation (WHO, in 1966),
“Drug is any substance or product that is used to
prevent or cure diseases in human beings or animals”.
OR
“Drug is defined as “any substance or product that is
used to modify or explore physiological systems or
pathological states for the benefit of recipient.”
OR
Drugs are also defined as, “synthetic or
natural substances or product which are used to
relieve discomfort and restore a state of well being.”

81. A drug is any substance
that, alters normal
bodily function,
resulting any
psychological or
behavioral change.
OR
 Drug is a substance
used to treat an illness.
Drugs:

82. pramodpadole@gmail.com Dr P. R. Padole
Requirements for An ideal drug :
First Second Third Fourth
Action
should be
localized
at the site
where
it is
desired to
act
Act on a
system
with
efficiency
and
safety
Not be
toxic
Minimum
side
effects

84. LOGO
pramodpadole@gmail.com
ANALGESICS
&
ANTIPYRETICS:

85. LOGO
ANTIPYRETICS:
Q.1) What are antipyretic drugs? (S-11, W-11, W-14,W-7 & W-19, 1-2 Mark)
Q.2) What are analgesics & antipyretics?
Q.3) Substances which reduce body temperature in high fever are called antipyretic.
ANTIPYRETICS:
Defination:
The substances which reduce body
temperature in high fever are called as antipyretics.
Antipyretics are also analgesics.

86. LOGO
Do you know?

87. LOGO
ANALGESICS:
ANALGESICS:
 The substances (compounds) which
relieves pain are called analgesic.
Or
 The compounds which reduce the pain are
called as analgesic.
Q.1) What are analgesic drugs? (W-11 & S-18, 1-2 Mark)
Q.2) The compounds which relieve the pain are called as analgesic.
Q.3) Narcotics are the substances which produce sleep and unconsciousness.
Q.4) The compounds which reduce the pain are called as __________. (W-15, ½ Mark)

88. Types of ANALGESICS:
Narcotics:
are chemical
substances which
produce sleep
and
unconsciousness.
ANALGESICS:
Pain Relief
Non-
norcotics:
do not cause
addiction
e.g.
Phenylbutazone

91. My student still waiting about Non-norcotics:
Non-norcotics:
do not cause addiction.
The most important non-norcotic
analgesic is Phenylbutazone
(Butazolidine)
Bali
Amravati

92. B.Sc.-II (Sem-IV) Unit No. – III
B) REACTIVE METHYLENE COMPOUNDS:
CH3 C CH2 C OC2H5
O O
CH2 C OC2H5
O
Ethylaceto acetate or
Acetoacetic ester (AAE)
Diethylmalonate or
Malonic ester
C2H5O C
O
Active
Methylene Groups
EWG
EWG
Acetyl gp Ester gp
EWG
( - Hydrogens)
When methylene group (-CH2-) is present between two strongly electron
withdrawing groups (EWG) such as -COCH3, -COOC2H5 or -CN; then
hydrogens of methylene group are acidic and reactive, called as reactive
methylene group.
Compound containing reactive methylene group is called as reactive methylene compound.

93. Phenylbutazone (Butazolidine)
 Preparation or Synthesis of Phenyl-butazone (Butazolidine):
Q.1) Give synthesis and uses of Phenylbutazone. (S-16, W-16, S-18 & W-19, 4 Mark)
Q.2) What kind of Phenylbutazone drug is?
Q.3) Phenylbutazone is a non-norcotic type of analgesic.
Q.4) Phenylbutazone is___________
a) Antimalarial b) Sulpha drug c) Antipyretic d) Non-norcotic analgesic
Q.5) Describe synthesis and uses of Phenylbutazone. (S-19, 4 Mark)
HC
C OC2H5
O
C
O
OC2H5
Diethyl Malonate
C2H5ONa
C4H9 Br CH
C OC2H5
O
C
O
OC2H5
C4H9
Diethyl butyl Malonate
N-H
C6H5
N-H
C6H5
Diphenyl hydrazine
C6H5 N
N
C
O
C6H5
C
O
C
H
C4H9
Phenyl butazone
(Butazolidine)
H
+ + HBr
n-butyl bromide
C
C
C2H5O
O
C
O
C2H5O
C4H9
Diethyl butyl Malonate
+ + 2 C2H5OH
Step-1) Preparation of Diethyl butyl malonate from Diethyl malonate & n-butyl bromide
Step-2) Preparation of Phenyl butazone from Diethyl butyl malonate & Diphenyl hydrazine
H

94. pramodpadole@gmail.com
Uses of Phenylbutazone :
Uses
of
Phenyl
butazone
More than one week because it is toxic
Therapy of acute attack of gout
Treatment of spondylites
with aspirin is used as a strong medicine
to cure rheumatoid arthritis (Joints deformities)
Mild analgesic & antipyretic
Toe & foot caused by defects in Uric acid metabolism

96. By Dr. P. R. Padole
SULPHA DRUGS:
SULPHA DRUGS:
‘Sulfa drugs’ were some of the original antibiotics,
and are still in use today.
These are substituted sulphanilamides.
These contain sulphonamide (─SO2NH2)
group in their structure.
These were used to cure bacterial infections in
human beings.
Q.1) What are sulpha drugs? (W-11, W-12, W-13, S-17 & W-18, 1-2 Mark)
Q.2) What are sulpha drugs? Which structural unit these contain?

97. SULPHA DRUGS:
 They have played an important role in curing diseases like
pneumonia, dysentery, etc.
 They may be prescribed to treat urinary tract infections
(UTIs), bronchitis, eye infections, bacterial meningitis, pneumonia,
ear infections, severe burns, traveler's diarrhea, and other conditions.

98. Types of SULPHA DRUGS:
1. Sulphanilamide
2. Sulphaguanidine
3. Sulphapyridine
4. Sulphathiazole
5. Sulphadiazine

99. LOGO
Do you know?
Sulphanilamide

100. LOGO
Sulphanilamide:
 Preparation or Synthesis of Sulphanilamide:
Q.1) Give the preparation and uses of Sulphanilamide.
(W-09, W-11, S-12, W-13, S-15, W-18 & W-19, 4 Mark)
Q.2) Sulphanilamide is _____________.
a) Antibacterial b) Antimalarial c) Analgesic d) Antipyretic
Q.3) How sulphanilamide is prepared? (S-17, 4 Mark)
Uses:
Sulphanilamide has antibacterial power and is used in medicine against
“cocci – infections” such as streptococci, gonococci and pneumococci.
It is cheapest sulpha drug.
N
Acetanilide
H
C
O
CH3 N
N4 - Acetyl sulphanilyl
chloride
H
C
SO2-Cl
O
CH3 N
N4 - Acetyl sulphanilyl
amide
H
C
SO2NH2
CH3
H+
/ HOH
N
Sulphanilamide
H
H
SO2NH2
Cl SO3H
Chlorosulphonic acid
Chlorosulphonation + NH3
O
Acid Hydrolysis
H HO-SO2-Cl
- H2O
H-NH2
- HCl
1
2
3
4
H OH
+ CH3COOH
Sulphanilamide (p- amino benzene sulphonamide)

101. Do you know?
Sulphadiazine:

102. Sulphadiazine:
Q.1) Give the preparation and uses of Sulphadiazine. (W-15, S-17 & S-18, 4 Mark)
Q.2) For what purpose the sulphadiazine drug is used?
Q.3) Sulphadiazine can be synthesized by oxidation of 2-aminopyrimidine with p- acetylsulphanilyl chloride
followed by alkaline hydrolysis.
Q.4) Sulphadiazine is synthesized from___________.
a) Acetanillide b) Quinoline c) Dithiocarbamate d) Anthranilic acid
Q.5) Sulphadiazine is synthesized from___________. (S-17, ½ Mark)
a) Acetanillide b) Quinoline c) Sulphanilamide d) Acetone
Q.6) How the drug sulphadiazine is prepared? Give its uses. (W-17, 4 Mark)
Sulphanilamide
(p- amino benzene sulphonamide):
Sulphadiazine:
H2N SO2NH
N
N
Sulphadiazine
Pyrimidine
sulphonamide (─SO2NH2) group

103. Preparation of Sulphadiazine:
Uses:
1) Sulphadiazine is eight times active than sulphanilamide and is used for the
cure of bacterial infections.
2) It is much less toxic, absorbed slowly by intestinal tract and also excreted slowly.
H3C C
O
NH
Cl-SO3H
-HOH
H3C C
O
NH SO2-Cl
Acetanilide N4-acetyl sulphanilyl chloride
N
N
H-HN
2-amino pyrimidine
Pyridine
H3C C
O
H
N SO2 NH
N
N
aq. NaOH
H2N SO2-NH
N
N
Sulphadiazine
H + HO-SO2-Cl
or
Chlorosulphonic acid
+
Condensation
-HCl
HO H
Alkaline hydrolysis
+ CH3COOH

104. Digestive System
CB/V/1718 of 10
10
Uses of Sulphadiazine:
Mouth
Anus
Oesophagus
Pharynx (throat)
Stomach
Small
Intestine
Large
Intestine
Alimentary
Canal
or
Digestive
Tract
It is much less toxic, absorbed slowly by intestinal tract and also excreted slowly.
H2N SO2NH
N
N
Sulphadiazine

106. Telephonic Talk between

108. LOGO
ANTIMALARIALS:

109. www.themegallery.com
ANTIMALARIALS:
Antimalarials are chemical substances
used to lower down malarial fever.
Examples: Chloroquine, quinine,plasmochin etc.
Q.1) What are antimalarial drugs? (W-18, 1 Mark)
Q.2) What are antimalarials?
Q.3) What are antimalarials? Give synthesis of Chloroquine from 4,7- dichloroquinoline? Give
uses of chloroquine.
Q.4) How chloroquine is useful as an antimalarial?
Q.5) What are the two reactants which on condensation give chloroquine drug?
Q.6) The chemical substances used to lower down malarial fever are called antimalarial.
Q.7) Chloroquine is a drug which is active against all species of plasmodia.
Q.8) 4,7-dichloroquinoline is used in the synthesis of Chloroquine drug.
Q.9) 4,7-Dichloroquinoline is used for the synthesis of ______________
a) Phenylbutazone b) Sulphadiazine c) Chloroquine d) Sulphanilamide
Q.10) Chloroquine is used for the following treatment _____________.
a) To reduce malarial fever . b) To relieve Pain c)To kill Plasmodium species d) To produce sleep
Q.11) Give the synthesis of Chloroquine from 4,7- dichloroquinoline. (S-16 & W-17, 4 Mark)
Q.12) How the drug chloroquine is synthesized ? Give its uses. (W-16, 4 Mark)
a) Acetanillide b) Quinoline c) Sulphanilamide d) Acetone
Q.13) What are antimalarial drugs? Give synthesis of Chloroquine. (W-18, 4 Mark)
Q.14) Write synthesis and uses of Chloroquine. (S-19 & W-19, 4 Mark)

110. Chloroquine:

111. www.themegallery.com
Preparation of Chloroquine:
Step-1) Preparation of 4,7-dichloroquinoline:
NH-H
Cl
3-Chloro aniline
C2H5
O
C
C
O
C
H
O
Ethyl ester of
formyl acetic acid
Cl
N
CH
CH
C
O
O
C2H5
Enamine
250 0
C
N
Cl
O H
7-Chloro-4-hydroxy
Quinoline
- POCl3
N
Cl
Cl
4,7-Dichloro Quinoline
1
2
3
H
H - H2O
H
H
(1) - C2H5OH
PCl3-Cl
Cl
+ PCl5
- HCl
1
2
3
4
5
6
7
(2) Aromatization
CH3 C CH2 C OC2H5
O O
Ethylaceto acetate or
Acetoacetic ester (AAE)
EWG
Acetyl gp
EWG

112. www.themegallery.com
Preparation of Chloroquine:
 Step-2) Preparation of 4-diethylamino-1-methylbutylamine
from AAE:
O
C
C
C
C2H5 O
O
CH3
Acetoacetic ester
(AAE)
Cl CH2 CH2 N
C2H5
C2H5
N,N-diethyl-2-chloro ethane
Na
O CH
C
C2H5 - O
O
CH3
C
C
N
C2H5
C2H5
2-Diethyl amino ethyl acetoacitic ester
i) Hydrolysis by
O
C
C
CH3
C
C
N
C2H5
C2H5
1-Diethyl amino-4-pentanone
H2N
CH
C
H2
CH3
H2
C
C
H2
N
C2H5
C2H5
4-Diethyl amino-1-methyl buthyl amine
-CO2
H
H 1
2 - HCl
H2
H2
HCl
ii) Decarboxylation
HO-H
(- C2H5OH)
H2
H2
H2
i) Reduction by Raney Ni
(- H2O)
(i.e., >C=O >CH2)
ii) Reaction with NH3
(i.e., >CH-H >CH-NH2)
1
2
3
4
(Note that: AAE
CH3-C-CH2-C-OC2H5)
O O

113. www.themegallery.com
Preparation of Chloroquine:
 Step-1) Preparation of 4,7-dichloroquinoline:
 Step-2) Preparation of 4-diethylamino-1-methylbutylamine from AAE:
 Step-3) Condensation of these two
compounds; to form Chloroquine as a product:
Step-1 Step-2
HN
CH
C
H2
CH3
H2
C
C
H2
N
C2H5
C2H5
4-Diethyl amino-1-methyl buthyl amine
1
2
3
4
N
Cl
Cl
4,7-Dichloro quinoline
N
HN
CH
CH3
C
H2
H2
C
C
H2
N
C2H5
C2H5
Cl
Chloroquine
H
- HCl

114. Uses of Chloroquine:
First use Third use
Second use
Exhibiting
the
antimalarial
activity
Treatment
of malaria
during
pregnancy
Prevention &
treatment
of Malaria
exhibiting the
antimalarial activity
exhibiting the
antimalarial activity

115. Company
LOGO C) Pesticides:
pramodpadole@gmail.com

116. Do you know?
Pesticides:

117. Pesticides:
Q.1) What are pesticides? How are they classified? (W-12, W-13, W-16 & W-17, 4 Mark)
Q.2) What are pesticides? (S-13, S-14 & S-18, 1-2 Mark)
Q.3) Explain the terms: Pesticides. (W-15 & S-17, 2 Mark)
Q.4) What are the merits and demerits of using pesticides?
Q.5) Chemicals which are used to kill insects, fungi and weeds are called pesticides.
Defination:
Chemicals which are used
to kill insects, fungi and weeds
are called pesticides.
C
C
C
C
C
C
H
H
H
H
H
H
Benzene
+ 3 Cl2
C
C
C
C
C
C
H
H
H
H
H
H
Cl
Cl
Cl
Cl
Cl
Cl
sun light
Benzene hexa-chloride (B.H.C.)
(or Hexachloro-cyclohexane)
B.H.C. is insecticides, rarely used, harmful effects

118. Classification of Pesticides:
A
INSECTICIDES:
B
HERBICIDES:
C
FUNGICIDES:
D
RODENTICIDES:
Pesticides
I H F R

119. Dr. P. R. Padole
INSECTICIDES:
Organic
Insecticides:
stable to light and heat
Examples:
D.D.T.,
B.H.C.
Insecticides
Insects killer
Pesticides which destroy insects
are called as insecticides.
Phosphate
Insecticides:
poisonous to insects
Examples:
? ? ?

120. Malathion:
MALATHION (Insecticide):
Q.1) Give the method of preparation and uses of Malathion. (S-13, S-14, W-16, W-18 & S-19, 4 Mark)
Q.2) Write down the preparation of Malathion.
Q.3) Give method of preparation of Malathion, its importance to farmers and show how it is better than D.D.T.
Q.4) Write examples of organophosphate insecticide with formula and what is the mode of its action.
Q.5) Give any two uses of Malathion.
Q.6) Malathion is a organophosphate insecticide.
Q.7) What is Malathion? (W-15, 1/2 Mark)
a) Insecticide b) Herbicide c) Fingicide d) Rodenticide
+ P2S5 (CH3O)2 P
2 SH
S
+ H2S
Methyl
Alcohol
Phosphorous
Pentasulphide O,O'-Dimethyl dithiophosphate
4 CH3OH
Step-1) Preparation of O,O'- dimethyl dithiophosphate from Methyl alcohol & P2S5:
Step-2) Preparation of Malathion from O,O'- dimethyl dithiophosphate:
(CH3O)2 P S H
S
CH-COOC2H5
CH-COOC2H5
O,O'-Dimethyl dithiophosphate
Diethyl maleate
CH3O
P S
S
CH.COOC2H5
Malathion
CH2.COOC2H5
CH3O

121. Uses of Malathion:
Malathion is a potent and effective
insecticide against insects, fungi and
weed. It has the merit of being less
toxic to mammals.
It is not hard insecticide. It can be
easily degraded by environmental
conditions. Thus it leaves no ill
effects.
It is a real boon to the farmers to
protect the crops from pests and
insects.

122. LOGO HERBICIDES:
 2,4-D is a synthetic auxin herbicide:
 2, 4 Dichloro-phenoxy-acetic acid (Herbicide):
Q.1) What are Herbicides? Give uses of [2, 4-D].
Q.2) Write the formula and name of [2, 4-D].
Q.3) What are herbicides? (S-17, 1 Mark)
Q.4) Pesticides which are used to destroy unwanted weeds in the crop are called herbicides.(S-16 & W-17, ½ M)
Q.5) What are herbicides? Give example. (S-17 & S-18, 2 Mark)
Q.6) Complete the following reaction and name the product formed in each of the reaction: (S-15, 2 Mark)
Q.7) Draw the structure of : 2, 4-D. (W-14, 1 Mark)
Q.8) Draw the correct structures of 2, 4D. (S-15, 2 Mark)
Q.9) Give any one method of preparation of [2, 4-D].
Q.10) Give any two uses of 2,4-D.
Q.11) 2,4-dichlorophenol with chloroacetic acid gives 2,4-D (2, 4 Dichloro-phenoxyacetic acid).
Q.12) Chlorination of phenoxyacetic acid gives 2,4-D (2, 4 Dichloro-phenoxyacetic acid).
Q.13) What is 2,4- D?
a) Insecticide b) Herbicide c) Fungicide d) Rodenticide
Q.14) How will you prepare [2, 4-D] from 2,4-dichlorophenol? (S-16 & S-18, 4 Mark)
Q.15) What are the different uses of [2, 4-D]? (W-15, 4 Mark)
Defination:
Pesticides which are used to destroy unwanted weeds in
the crop are called herbicides.
Cl
OH
Cl
2, 4- dichlorophenol
Cl CH2 C OH
Chloroacetic acid
O
?

123. Preparation of [2, 4-D]
(2, 4 Dichloro-phenoxyacetic acid) :
Method-1) When phenol is reacted with chlorine (two moles); to form
2, 4-dichlorophenol, which is further reacted with chloroacetic acid; to form
2, 4-D (2, 4 Dichloro-phenoxyacetic acid).
Cl
C
H2
O
OH
C
Cl
O
2, 4-Dichloro-phenoxy-acetic acid
[2, 4-D]
1
2
3
4
O-H
Cl
2, 4- dichloro-phenol
Cl CH2 C OH
Chloroacetic acid
O
OH
Phenol
Chlorine
2 Cl2
H Cl
(-2 HCl)
H
+
-HCl
Cl--Cl
Cl-Cl

124. Preparation of [2, 4-D]
(2, 4 Dichloro-phenoxyacetic acid) :
Method-2) When phenol is reacted with chloroacetic acid; to form
phenoxyacetic acid, which is further reacted with chlorine (two moles);
to form 2, 4-D (2, 4 Dichloro-phenoxy-acetic acid).
Cl--Cl
Cl-Cl
O
Phenol
H2C C OH
O
H Cl O
O
OH
Phenoxy-acetic acid
Cl
C
H2
O
OH
C
Cl
O
2, 4-Dichloro-phenoxy-acetic acid
[2, 4-D]
+ 2Cl2
+ 2 HCl
H
H
- HCl
Chloroacetic acid
1
2
3
4

125. By Dr. P. R. Padole
Uses of [2, 4-D]:
First
Control of broadleaf
weeds BENZOIC ACID
2
2,4-D used as a
Herbicide in the world
Third
In laboratory for
plant research
synthetic auxin (plant hormone)

127. Do you know?
FUNGICIDES:
Q.1) What are fungicides?
Q.2) Chemicals which destroy fungi are called fungicides.
Q.3) Explain the term: Fungicides. (W-15 & W-18, 2 Mark)
Q.5) What are fungicides? Give example. (S-17, 2 Mark)
Q.6) Tea tee oil can be used as: (S-19, ½ Mark)
(a) Insecticide (b) Herbicide (c) Fungicide (d) Rodenticide

128. Chemicals which destroy such fungi
are called fungicides.
Pests are insects or
Small animals which
Damage crops or food
Supplies.

129. LOGO
THIRAM (Fungicide):
Q.1) Give any one method of preparation or synthesis of Thiram and its uses. (S-16, 4 Mark)
Q.2) What is the name of Thiram? (W-18, 1 Mark)
Q.3) Which chemical is used to prevent fungal diseases in seed and crops?
Q.4) Give any two uses of Thiram.
Q.5) Tetramethyl Thirum disulfide is also known as Thiram.
Q.6) What is Thiram?
a) Insecticide b) Fungicide c) Herbicide d) Rodenticide
Q.7) Tetramethyl thirum disulfide is____________.
a) Insecticide b) Herbicide c) Fungicide d) Rondenticide
Q.8) Which one of the following is used in the synthesis of Thiram?
a) Phenol b) Anthranilic Acid c) Phenolphthalein d) N,N-dimethyldithiocarbamate salt
Q.9) Which one of the following is used to prevent fungal diseases in the seed and crops?
a) D.D.T. b) 2,4-D c) Thiram d) Malathion
Q.10) Thiram has been used in the treatment of human scabies and as sun screen and as
bactericide applied directly to the skin.
Q.12) Give the method of preparation and uses of Thiram. (W-17 & S-19, 4 Mark)

130. LOGO
Preparation of THIRAM:
(Tetramethyl thiuram disulphide)
 Oxidation of N,N-dimethyl dithiocarbamate with H2O2 / Cl2 / I2
/ air; to form THIRAM (Tetramethyl thiuram disulphide).
OR
S
C
S
N
H3C
H3C
Na
Sodium salt of
N,N-Dimethyl dithio carbamate
Careful oxidation with
H2O2 / Cl2 / I2 / air
H3C
N
H3C
C
S
S S
C
S
N
CH3
CH3
Thiram
(Tetra methyl thiuram disulfide)
S
C
S
N
CH3
CH3
Na
+
Cl
Cl
Sodium salt of
N,N-Dimethyl dithio carbamate
- 2 NaCl
+

131. Uses of Thiram:
Accelerator and vulcanizing agent
Prevent fungal diseases in seed and crops
Treatment of human scabies,
as a sun screen
Animal repellent to protect
fruit trees

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Do you know?
RODENTICIDES:

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RODENTICIDES:
Rodenticides are pest control chemicals which
are used to kill rodents.

134. www.themegallery.com
RODENTICIDES:
Q.1) Rodenticides are pest control chemicals which are used to kill rodents. (W-16, ½ Mark)
Q.2) Explain the term: Rodenticides. (S-17 & W-18, 2 Mark)
Q.3) What is meant by Rodenticides? (S-18, 1 Mark)

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