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Polymers: Chapter - 00
Polymers: Chapter - 00
CHAPTER - 00
POLYMERS
• Polymers are bigger organic molecules possessing large molecular mass (103 – 107 u)
• Poly means ‘many’ and mer means ‘unit’.
• The individual unit is monomer
• The process of combination of different monomers to form polymer is called polymerisation.
Eg : n moles of ethene on polymerisation gives polythene.
CLASSIFICATION OF POLYMERS
I. BASED ON SOURCE
i. Natural polymers
The polymers found in plants and animals.
Eg : Natural rubber, silk, cellulose, starch, protein, glycogen
ii. Synthetic polymers
Man made or artificial
Eg : Polyethene, polypropylene, polystyrene, Nylon, Teflon, PVC, Bakelite etc
iii. Semi-synthetic polymers
Derivatives of natural polymers
Eg : Vulcanised rubber - Rubber + Sulphur
Cellulose acetate - Rayon
Cellulose nitrate - Gun cotton
II. BASED ON STRUCTURE
I. Linear polymers
Polymers which contains various linear chains, so they can be arranged very compact.
Possess high density, M.P and tensile strength.
Eg : Natural rubber, amylose, High Density Poly Ethene (HDPE), Nylon, Teflon, Poly Acrylo Nitrile
(PAN).
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Plasticisers : The organic compounds which are added to thermoplastics to make then more soft
on heating. Eg: dialkyl phthalates
iv. Thermosetting plastics
Highly branched on cross-linked. Upon heating they undergo extensive cross linking to give hard
infusible and insoluble mass. So they cannot be recycled. Eg : Bakelite, Melmac, Urea-HCHO
resin. Decreasing order of force of attraction Thermosetting >Fibre > Thermoplastics > Elastomers.
IV. BASED ON TYPE OF MONOMERS
i. Homopolymers
Contains only one type of monomers. Eg : Polythene, Polypropylene, Polystyrene, PVC, Teflon,
Natural rubber, Neoprene, Nylon-6 etc.
ii. Copolymers
The polymers which contain more than one type of monomer.
Eg : Buna-S, Buna-N, Nylon-6 6, Nylon-610, Bakelite, Melmac, Terylene etc.
V. BASED ON MODE OF POLYMERISATION
i. Addition or chain growth polymers
The polymers formed by the repeated addition of monomers containing double or triple bond.
Eg : Polyethene, PP, PVC, Teflon, Natural Rubber, Buna-S, Buna-N, Neoprene etc. There are
three types of mechanism.
a. Free radical polymerisation
Eg : Preparation of LDPE, PVC, PP, Polystyrene etc.
Polymerisation
nCH 2 CH 2
Benzoylperoxide
CH2 CH2 n
Chain initiation:
MECHANISM IS FREE RADICAL POLYMERISATION
Step-I : Initiation step
O O O
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C 6H 5 + C H 2 CH2 C 6H 5 CH 2 CH2
C6H 5 CH 2 CH 2 CH 2 CH 2
C 6H 5 CH 2 CH 2 + CH 2 CH 2
C 6H 5 CH 2 CH 2 CH 2 CH 2
n
b. Cationic polymerisation
Monomers with Electron donating group participate in this
This occurs in acid medium in presence of proton acids such as H2SO4 or Lewis acids like BF3, AlCl3
etc. Intermediate is carbocation
c. Anionic polymerisation
Noticed in alkene molecules having Electron withdrawing group such as phenyl, chloride, Cyanide etc
This is carried out in presence of suitable bases such as sodaamide, N-butyl lithium etc.
Intermediate is carbanion.
ii. Condensation polymers or step growth polymers
Polymers formed by repeated condensation between bifunctional or trifunctional monomers. In this
polymerisation, there is elimination of small molecules like H2O, HCl, NH3 etc.
Eg : Nylon-6, Nylon-66, Nylon-610, Terylene, Bakelite, Melmac etc.
Eg : Nylon-66
n NH 2 CH 2 6 NH 2 + n HOOC CH 2 4 COOH
Hexamethylene diamine Adipic acid
O O
nH 2O
HN (CH 2 )6 NH C (CH 2) 4 C
n
Nylon-6 6
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condensation
II A B A ABA
Trimer
condensation
III A B A B A BAB
Tetramer
Polymer
n1M1 n 2 M 2 n 3 M 3
Then M n
n1 n 2 n 3 ...........
ni Mi
Mn
ni
Measured by osmotic pressure method.
n1M12 n 2 M 22 n 3 M 32 .....
n1M1 M1 , n 2 M 2 M 2 , n 3M3 M3 .... M w n1M1 n 2 M 2 n 3 M 3 .....
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n i Mi2
Mw
niMi
Mw
• PDI =
Mn
• For natural polymers, PDI = 1 ie monodisperse polymers
• Synthetic polymers, PDI > 1 ie polydisperse polymers
SOME IMPORTANT ADDITION POLYMERS
I. Poly olefines
A. Polyethene
LDPE
Polythene
HDPE
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333 343 K
CH 2 CH 2
Preparation : nCH 2 CH 2 6
7 atm
n
Zieglar Natta catalyst
CH 3
Properties:
• Homo polymer
• Thermoplastic
• Stronger and harder than polythene
Uses
For packing textiles and food
For making strong pipes, bottles, seat covers, carpet fibres etc
C. Polystyrene (styron) Or (PS)
Organic
Preparation : nC6 H 5 CH CH 2
peroxide
CH CH2 n
Styrene
C6H5
Polystyrene
Properties:
• Homopolymer
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• Thermoplastic
• Transparent
• Floats over water
• Soluble in organic solvents
Uses
Used for making ceiling tiles
Lining material for electronic items
II. Polyhaloolefines
A. Poly vinyl chloride (PVC)
Organic peroxide
Preparation : nCH 2 CH 2
or NaNH 2
CH 2 CH
n
Anionic polymerisation
Cl Cl
Properties:
• Linear
• Homopolymer
• Can be easily moulded
Uses:
Making raincoat, hand bag, pipe, toys, electrical insulators etc.
B. Poly Tetra Fluro Ethylene (PTFE) or TEFLON
F2 C CF2 ammonium
highperoxi
disulphate
CF 2 CF 2
pressure n
Properties
• Linear
• Homopolymer
• Chemically inert
• Stable upto 598 K
• Resistant to attack by corrosive reagents
Uses:
• Used for making oil seals, gasket, coating cookwares.
III. Poly Acrylates
A. Poly Acrylo Nitrile (PAN) or ORLON or Acrilan
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FeSO 4 H 2O 2
nCH 2 CH
Fenton 's reagent
CH2 CH n
CN CN
Vinyl cyanide PAN
(Acrylonitrile)
Properties
• Linear
• Homopolymer
• High M.P.
• Fibre
• Hard
Uses:
Substituent of wool
Used for making blankets and synthetic carpets
B. Poly methyl metha Acrylate (PMMA) Plexi glass/Leucite/Perspex
CH 3 CH 3
Benzoyl peroxide
nCH 2 C CH 2 C
COOCH3 COOCH3
Methyl metha acrylate PMMA
Properties:-
• Homopolymer
• Hard
• More transparent than glass
• Shows good optical clarity
Uses:
• Making lenses
• Aircraft windows
• Transparent domes etc
IV. Polybutadienes
A. Natural rubber - cis poly isoprene
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CH 2 C CH CH 2
CH2 CH2
C C
CH3
CH3 H
2-methyl-1,3 butadiene (isoprene)
Cis poly isoprene
• Amorphous
• Natural
• Elastic
• Linear
Gutta percha
It is trans isomer of rubber ie trans poly isoprene - GUTTA PERCHA
• Linear
• Amorphous
• Natural
• Non-elastic
It is used by dentists to fill the teeth.
B. Neoprene Rubber
Properties:
• Homopolymer
• Vegetable oil and mineral oil resistant
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Uses:-
Making conveyer belt, gasket, stoppers, printer rollers etc.
C. Buna-S (Styrene-Butadiene Rubber - SBR)
nCH 2 CH CH CH 2 nC6 H 5 CH CH 2
1,3 butadiene
3 :1 ratio
Na
CH2 CH CH CH2 CH CH2 n
Buna -S
Properties
• Co-polymer
• Rubber like polymer
• Resistant to gasoline or oil
Uses
• To make automobile tyres
• Rubber sole, belt
• Water proof shoes
• Chewing gum etc
D Buna-N (Nitrile rubber)
Na
nCH 2 CH CH CH 2 nCN CH CH 2
1,3butadiene acrylonitrile ( vinyl cyanide)
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Vulcanisation
• Natural rubber becomes soft at high temperature (above 335 K)
• And brittle at low temperature (less than 283 K)
• Shows high water absorption capacity
• It is soluble in non-polar solvents and is non-resistant to attack by oxidising agents.
• To improve its physical properties, natural rubber is heated with small amount of s at 373 K - 415 K.
This is called vulcanization.
• During this sulphur crosslinking takes place at the double bonds of rubber and the rubber get stiffened.
CH3 H
CH2 C C CH2
373-415 K
+ S
CH2 C C CH2
CH3 H
CH3 H
CH2 C C CH2
S S
CH2 C C CH2
CH3 H
Notes:-
% of S in vulcanised rubber for making various products.
1–3% S Rubber band
3–5% S Automobile tyre
20–30% S Ebonite
35%S automobile battery cases
SOME IMPORTANT CONDENSATION POLYMERS
I. POLYESTERS
A. Terylene or Dacron
• Copolymer
• Grease resistant and durable fibre
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• Linear
O O
O CH2 CH2 O C C
n
Uses:
• For making clothes by mixing with cotton
• For making safety belt
• A form of it is used to make bottles (PET) - Poly Ethylene Terephthalate
B. Glyptal or alkyd resin
COOH COOH
HO CH2 CH2 OH + n
H2 O
Phthalic acid
O O
CH2 CH2 O C C
O n
Glyptal
Properties:
• Co-polymer
• Thermoplastic
• Soluble in suitable solvents
Uses:
• Used for making paints and lacquers (varnishes)
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II. POLYAMIDES
A. Nylon-6,6
O O
N (CH2)6 N C (CH2)4 C
n
nH 2 O
H H
Properties:
• Fibre
• Possess high tensile strength
• High modulus
Uses
• To make sheets, parachute and bristles of brushes
• In textile, its blended with wool to make socks and sweaters
B. Nylon 6(Perlon)
O
O
C
N H H2 O
C (CH2)5 NH n
530 540 K
Nylon-6
Caprolactum
Mechanism
OH O
[O]
[O]
Cyclohexane
Cyclohexanol Cyclohexanone
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O
N OH
C
conc.H 2SO 4
N H
NH 2 OH
Beckman 's rearrangement
Cyclohexanone oxime
Caprolactum
H2O
HOOC (CH 2 ) 5 NH 2 Polymerisation 530540 K
nH 2 O
Aminocaproic acid
C (CH2)5 NH
n
Nylon 6
Properties
• Homopolymer
• Fibre
Uses
• For making fabrics, ropes and tyre cord.
III. FORMALDEHYDE RESINS
A. Phenol formaldehyde resins
Linear
Novolac
Phenol + Formaldehyde
Cross linked
Bakelite
i. NOVOLAC
H H
+
H /OH
C O +C O
H
H
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OH OH OH
H H
CH2OH
C O CH 2O
H
OH OH OH
CH2OH
HCHO H+/OH
CH2OH
o & p hydroxy methyl phenols
• o-hydroxy methyl phenol on condensation polymerisation gives linear polymer NOVOLAC (used in
paints).
OH OH OH OH
CH2OH CH2 CH2 CH2 CH2
nH2O
NOVOLAC
II) BAKELITE
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OH CH 2OH
CH2OH
nHCHO
OH
OH OH OH
H2C CH2 CH2 CH2
Properties
• Cross linked
• Rigid
• Hard
Uses
• Soft bakelite is used to make binding glue for wood
• Hard bakelite used for making electrical switches, combs
• Barrels, handles of various utensils etc.
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B. Melamine - HCHO Resin
N
H2N NH2
n n CH 2O
nH 2 O
N N
NH2
2,4,6 Triamino- 1, 3, 5- triazine (melamine)
Properties
• Co polymer
• Rigid
• Hard
• Brittle
N
NH NHCH2
N N
NH
Melmac
Uses
• Used for making unbreakable crockery
C. Urea-HCHO Resin
O O
nNH2 C NH2 + nCH2O NH C NH CH2
nH 2 O n
Properties:
• Rigid
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• Hard
• Brittle
Uses:
Used to make unbreakable cups and plates and laminated sheets.
BIO DEGRADABLE POLYMERS
The polymers which contain functional group similar to bio-polymers.
1. Dextron
• The first biodegradable poly ester
• It is polyglycolic acid - polylactic acid
• It is used as suture (Thread for stitching wound)
OH
OH
O O
nH 2 O
O CH CH2 C O CH CH2 C
n
CH3 CH2
CH3 PHBV
Uses:
• Used in speciality packaging
• Orthopaedic devices
• In controlled drug release (outer covering of capsules)
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3. Nylon-2-Nylon-6
• Biodegradable poly amide
nH 2 N CH 2 COOH nH 2 N CH 2 5 COOH
Glycine
Amin o caproic acid
O O
HN CH2 C HN (CH2)5 C
n
Nylon-2 nylon-6
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CHAPTER - 00
BIOMOLECULES
• Lifeless organic substances which build up living organisms and are essential for their growth and
maintenance
• Eg: Carbohydrates, aminoacids, proteins, nucleic acid, vitamins, hormones, lipids
CARBOHYDRATES
• Hydrates of carbon
• General formula: Cx(H2O)y
• But all compounds satisfying this general formula is not a carbohydrate
Eg: Formaldehyde, Acetic acid
• All carbohydrates doesn’t follow this general formula
Eg: Rhammnose (C6H12O5)
2-Deoxyribose (C5H10O4)
• Carbohydrates can be defined as optically active poly hydroxy aldehydes or ketones or substances
which give them on hydrolysis
CLASSIFICATION OF CARBOHYDRATES
1. Based on hydrolysis
i) Monosaccharides
• Further hydrolysis not possible
Eg: Glyceraldehyde, Ribose, Glucose, Mannose, Galactose, Fructose, sorbose etc
ii) Oligosaccharides
• Gives 2-10 monosaccharides on hydrolysis
Its further divided into:
a) Disaccharides
Sucrose (C12H22O11) + H2O Glucose + Fructose
b) Trisaccharides
Raffinose (C18H32O16) + H2O Glucose + Fructose+Galactose
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c) Tetrasaccharides
Stachyrose + H2O Glucose + Fructose + 2 Galactose
d) Pentasaccharides, Hexasaccharides, Heptasaccharides etc
iii) Polysaccharides
• Gives Hundreds-thousands of monosaccharides
Eg: Starch, cellulose, glycogen etc
II) Based on taste
i) Sugars
• Sweet in taste
• It is further divided into reducing and non reducing sugars
a) Reducing sugar
• Reduce Tollen’s test, Fehling’s solution and Benedict solution
Contains a hemiacetal or hemiketal group
O O H
R
Hemiacetal
Eg: All monosaccharides (mannose, glucose, galactose, fructose etc) and oligo saccharides like
lactose, maltose etc
b) Non-reducing sugar
• Not reduces Tollen’s reagent
Contains acetal group
O O R
R
Acetal group
• Fehlings solution and Benedict’s reagent
Eg: Sucrose
ii) Non sugars
• Not sweet in taste
Eg: polysaccharides
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MONOSACCHARIDES
3C
Aldotriose
Eg: Glyceraldehyde
4C
Aldotetrose
Aldoses Eg: Erythrose, Threose
5C
Aldopentose
Eg: Ribose, Deoxyribose
6C
Aldohexose
Eg: Glucose, Mannose, Galactose
Monosaccharides
(CH2O)n
n=3 to 7
3C Ketotriose
Eg: Dihydroxyacetone
4C
Ketotetrose
Ketoses Eg: Erythrulose
5C Ketopentose
Eg: Ribulose
6C
Ketohexose
Eg: Fructose, sorbose
2) D and L configuration
• The spatial arrangement of groups or atoms with respect to central atom is known as configuration.
• The D and L configuration is assigned to aldoses and ketoses with respect to Fischer projection
formula of glyceraldehyde
• Glyceraldehyde: OHC–CHOH–CH2OH
CHO CHO
H * OH OH * H
CH2OH CH2OH
D-glyceraldehyde L-glyceraldehyde
• In D configuration, OH group is on the right side of chiral C which is far away from aldehyde or
ketonic carbon
• In L configuration OH group is on left side of chiral C
• All naturally occuring sugars belong to D configuration
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GLUCOSE - C6H12O6
• Blood sugar
• Optically active-dextro rotatory
• Hence dextrose
• White crystalline solid
• Soluble in H2O
• Structural formula
O H
H C (CHOH)4 C OH
Preparation
1) From cane sugar (sucrose) by acid hydrolysis or hydrolysis in presence of enzyme called invertase
H /Invertase
C12H22 O11 H2O C 6H12O 6 C 6H12O 6
sucrose glu cos e fructose
CHO
Red P/HI n - hexane
(CHOH)4
CH2 OH
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OH
HCN
CH
CHO Glucose cyanohydrin
CN
(CHOH)4 (CHOH)4
CH2 OH
CH2 OH
NH2OH
CH N OH
CH2 OH
CHO COOH
Br2/H2O (CHOH)4 Gluconic acid
(CHOH)4
Mild oxidising agent
CH2 OH CH2 OH
CHO CHO
5(CH3 CO)2O/H2O
(CHOH)4 (CHOCOCH3)4
Acetylation
CH2 OH CH2 O CO CH3
Glucose pentaacetate
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CHO COOH
HNO 3
(CHOH)4 (CHOH)4 Saccharic acid (Glucitol)
Strong O.A.
CH 2 OH COOH
Indicate the presence of one 1°–OH group in glucose and remaining –OH is 2°.
From the above reactions, glucose is assigned an open chain structure and its Fischer projection
formula is:
CHO
H OH
*
OH H
*
H OH
*
H OH
*
CH2OH
D(+) glucose
Limitations of open chain structure of glucose
• Despite having an aldehyde group, glucose doesn’t answers 2, 4 DNP test, Schiff’s test, reaction
with ammonia and it not forms an addition product with sodium bisulphite
• The pentaacetate of glucose doesn’t react with hydroxyl amine
• The above two points indicates the absence of a free CHO group in glucose. Glucose is found to exist
in two crystalline forms. ie and . The form of glucose (mp 419K) is obtained by crystallisation
from conc. solution of glucose at 303K, while the form (mp 423K) obtained by crystallisation from
hot and saturated aqeous solution at 371 K
• From the above three points it is proposed that glucose forms a six-membered ring in which OH at C5
is involved in cyclic hemi-acetal link with CHO group
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1 * 1 1
H C OH O * H
H C HO C
2
H C* OH H
2
C* OH H
2
C* OH
3 3 3
HO C* H HO C* H HO C* H O
O
4
C*
4 4
H OH H C* OH H C* OH
5 5 5
H C* H C* OH H C*
6 6 6
CH2OH CH2OH CH2OH
6CH 6CH
2OH 2OH
H 5 O H H 5 O OH
O H H
1 4 1
4 OH H OH H
OH 3 2 OH OH 3 2 H
H OH H OH
Pyran
-D(+) glucopyranose -D(+) glucopyranose
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CHO
CH3OH H3CO C H
(CHOH)4 H C OCH3
Dry HCl
O
CH2OH (CHOH)3 O
(CHOH)
D(+) glucose H C C
CH2OH
CH2OH
D( )methyl glu cos ide D( )methyl glu cos ide
Anomers
Optical isomers which differ in configuration only around C1 in aldoses and C2 in ketoses. Examples:
1) D glucose and D glucose 2) D fructose and D fructose
Epimers
Optical isomers which differ in configuration other than C1 in aldoses and C2 in ketoses. Examples:
1) Glucose and mannose are C2 epimers 2) Glucose and galactose are C4 epimers
1 1 1
CHO CHO CHO
2 2 2
H OH HO H H OH
3 3 3
OH H HO H HO H
4 4 4
H OH H OH HO H
5 5 5
H OH H OH H OH
6 6 6
CH2OH CH 2OH CH2OH
D+ glucose D(+) Mannose D(+) Galactose
Muta rotation
The change in specific rotation of an optically active compound with time to an equilibrium value is
called muta-rotaiton.
Eg: Specific rotation of D glucose is +112° and that of D glucose is +19°. When either form is
dissolved in water and allowed to stand it gets converted into an equilibrium mixture of both with a few
amount in open chain form and specific rotation of solution changes and reach a constant value of
52.5°.
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H O
D()glucse
2
open chain structure
2 H O
D( )glu cos e
equilibrium mixture
% 36% 0.02% 64%
specific rotation 112 52.5 19
Fructose - C6H12O6
• Fruit sugar
• a ketohexose
• obtained along with glucose in hydrolysis of sucrose
• Belong to D-series but laevorotatory - Laevulose
Fischer projection formula for open chain and ring structure of fructose
1 1
HOH2C *C OH
CH2 OH
2
2 1
2
C O HO C CH2OH
HO *3 C H
3
O
3
C* H HO C* H
H *C OH OH
4
4 O
H
4
C* OH H C* OH
H *C
5
5
6 H
5
C* OH H C*
CH2OH
6
6 CH
2OH
CH2OH
D(-) fructose
D(-) fructose
D(–) fructose
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OH
H C H H C OH H C O
NaOH Tautomerism H C OH
C O C OH NaOH
D(+) Glucose
D(-) Fructose ene diol form intermediate
6 6
HOH2C 1
CH2OH
HOH2C
O O O OH
5 2 2
H OH OH H OH
4 5 4
H 3 H 3
CH2OH
1
OH H OH H
Furan
D(–) fructofuranose D(–) fructofuranose
DISACCHARIDES
• Carbohydrates which give two mono-saccharides on hydrolysis in presence of acid or enzyme
Glycosidic linkage
• The oxide linkage formed by the loss of a water molecule, when two monosaccharides are joined
together O
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Sucrose
• On hydrolysis gives D glucose and D fructose
CH2OH
H O H
H 1
4 OH H
OH O
3 2
glycosidic
H OH linkage
CH2OH
O
H OH
H CH2OH
OH H
Invert sugar
Dextrorotatory sucrose (+66.5°) on hydrolysis gives dextrorotatory glucose (+52.5°) and laevo rotatory
fructose (–92.4°). Therefore, the resulting mixture becomes laevorotatory. This is called inversion of
cane sugar and equimolar mixture of glucose and fructose is called invert sugar.
2) Maltose
• On hydrolysis gives two molecules of D glucose
• Glycosidic link is between C1 of 1st D glucose and C4 of 2nd D glucose.
• The aldehyde group of 2nd D glucose is free. So its a reducing sugar
C H 2O H C H 2O H
6 6
H O H H O H
5 5
H H
4 OH H 1 4 OH H 1
3 2 3 2 OH
OH O
H H OH
OH
-D (+)glucose -D (+)g lucose
M altose
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3. Lactose/Milk sugar
• On hydrolysis gives D galactose and of D glucose.
CH2OH CH2OH
6 6
OH O H O OH
5 5
H H
4 OH H 1 4 OH H 1
O 2
3 2 H 3
H H
H H OH
OH
-D(+) galactose -D(+) glucose
Lactose
POLYSACCHARIDES
1. STARCH
• (C6H10O5)n
• condensation polymer of D glucose
• Chief food reserve of plants and found in seeds roots, tubers etc
Eg: Rice, Potato, Banana
• Its a mixture of amylose and amylopectin
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Cellulose (C6H10O5)n
COOH COOH
H NH2 H2N H
R R
D-amino acid L-amino acid
• -amino acids are further classified into acidic, basic or neutral depends on number of COOH and
basic group
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NH2
NH2
NH2
NH2 NH2
CH2 CH COOH
NH2
• Histidine N H
N
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H2O
R CH COOH R CH COO
NH2 NH3
Zwitter ion
• In zwitter ion configuration acidic nature is due to NH3 and basic nature is due to COO–. So zwitter ion
form shows amphoteric behaviour
R CH COO CH H
R COO R CH COOH
OH
NH2 NH3 NH3
High pH (basic solution) zwitter ion Low pH (acidic solution)
anionic form cationic form
Isoelectric point
• In acid medium, amino acid exist as cations and migrate towards cathode. In basic medium, they
exist as anion and migrate towards anode under the influence of an electric field. But at a particular
pH they exist as zwitter ions and doesn’t migrate to any of the electrode. This is called isoelectric
point. At this pH amino acid shows minimum solubility.
Essential and Non-essential amino acids
Out of 20 amino acids required for protein synthesis, human body can produce only 10, they are
called non-essential amino acids. The remaining 10 amino acids which we require from food are
essential amino acids. They are
TTH VIP MALL
Threonine Valine Methionine
Tryptophan Isoleucine Arginine
Histidine Phenylalanine Leucine
Lysine
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O
1) H2 N CH2 COOH + H2N CH COOH
-H 2O
H 2N CH2 C NH CH COOH
glycine (Gly) peptide bond
CH3 CH 3
alanine (Ala) glycylalanine (Gly-Ala)
O
2) H2N CH COOH + H2N CH2 COOH -H2O H2N CH C NH CH2 COOH
Glycine peptide bond
CH3
CH3
Alanine (Ala) Alanylglycine (Ala-Gly)
Polypeptides
• Polymers of -amino acids contains 10-100 amino acid residues and possess molecular mass
upto 10,000 u
PROTEINS
• A polypeptide with more than 100 amino acid residues having molecular mass higher than 10,000u is
called a protein
• The word protein is derived from ‘proteios’ which means prime importance
• Proteins are most abundant biomolecules of living being
• Proteins contain elements like C, H, N, O, S. Some of this also contain. P, I and traces of metals like
Fe, Cu, Zn and Mn
Proteins
hydrolysis
Peptides
hydrolysis
Amino acids
STRUCTURE OF PROTEINS
I. Primary structure
• It refers to the sequence in which amino acids are linked to one another in a protein molecule. Any
change of this makes an entirely different protein molecule
• eg: In haemoglobin, instead of glutamic acid if valine comes, then it causes sickle cell anaemia
II. Secondary structure
• It refers to the conformation, which polypeptide chains assume as a result of H-bonding. This is of
two types
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i) - helix structure
• Given by Linus Pauling
• When the size of R-group is large- then intramolecular H-bonds are formed between CO of one
molecule and NH of the 4th amino acid giving a right handed -helix structure
• The CO and NH group of peptide bonds are trans to each other
ii) Pleated sheet structure
• When the size of R-group is small, intermolecular H-bonds are formed between CO of one polypeptide
and NH of the other chain giving a pleated sheet structure. In this conformation all polypeptide
chains are stretched out to nearly max. extension and then lay side by side
iii) Tertiary structure
• It represents the overall 3-D structure of proteins ie further folding of 2° structures
• Two snopes are possible: Fibrous and globular
Fibrous prote ins Globula r Prote ins
Consist of linear thread This structure result when
like molecules which the polypeptide chain, coil
tends to lie side by around to give a spherical
side to form fibres shape
The various chains are The chains are held together
held together by H- by H-bond and dipole
bond and disulphide interaction COO -…..NH3 +
bridging (salt bridge)
Insoluble in water Soluble in water
Stable to moderate Sensitve to change in
changes of temperature temperature and pH
and pH
Eg: Keratin (present in Eg: Fibrinogen, Albumin,
hair, skin, nail, wool) Haemoglobin, and all
myosin (present in enzymes
muscle) fibroin (present
in silk)
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iv Quarternary structure
• Some of the proteins are composed of two or more polypetide chains called subunits
• The spatial arrangement of these subunits with respect to each other is known as quarternary structure
• The best known example of a protein possessing quarternary structure is haemoglobin
• Its an aggregate of 4 polypeptide chains or subunits. Two chains contains 141 amino acid residue
each and other two contain 146 amino acid residues each. These 4 subunits are projected to the
vertices of a regular tetrahedron
• Haemoglobin total contains 574 amino acids
• Insulin contain 51 amino acids (30×1+21×1)
Denaturation of Proteins
• The loss of biological activity of protein when its native form is subjected to physical changes like
change in temperature or chemical change like change in pH is called denaturation
• In this water soluble globular proteins undergo coagulation to form water insoluble fibrous proteins
• During denaturation, 2° and 3° structure undergoes a change but 1° structure remains intact.
Examples:
1) Coagulation of egg white on boiling (during this entropy increases)
2) Curdling of milk
Some denaturations are reversible and is called renaturation
Biological functions of proteins
• Proteins acts as:
i) Structural materials - Keratin, Myosin, Fibroin
ii) Transport agents - Haemoglobin
iii) Biological catalyst or enzymes
iv) Receptors-Proteins which play a very important role in body’s communication
v) Metabolic regulators like insulin
vi) Antibodies
Chemical nature of enzymes
• Enzymes are globular proteins some are simple proteins, some conjugated
• Conjugated proteins contains aminoacid and non protenious part ie., Prosthetic group
• Prosthetic group is necessary for a protein to act as enzyme, so its termed as co-enzyme
• Protein part of conjugated protein is called apoenzyme
• The molecule as a whole is Holoenzyme
apoenzyme coenzyme
Holoenzyme
protenious
nonprotenious
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C and NH group
ii) Xanthoproteic test
• Amino acids with benzene ring + conc. HNO3 Yellow colour due to the nitration of benzene
iii) Millon’s test
• Phenolic amino acid + Millon’s reagent White ppt Red ppt.
5 5
HOH2C HOH2C
OH OH
4 O 1 O
H H 4 H H 1
3 2 3 2
H H H H
OH OH OH H
- D-ribose - D-2-deoxyribose
N N
guanine (G)
H2 N N N
Purine N N H
N N NH2
H N N
Adenine(A)
two ringed heterocyclic N N
4-N-atoms at 1, 2, 7 and 9 positions
H
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NH2
N
Cystosine (C)
O N
N
Pyrimidine O
N
N CH3 Thymine (T) in DNA
single ringed, heteroxydic
two N-atoms at 1,3 positions N
O
H
HN
Uracil (U) in RNA
O N
5'
HOH 2 C Base
O
4' H H 1'
H 3' 2'
OH OH
nucleoside
• When nucleoside is linked to phosphoric acid at 5’ position of sugar we get a nucleotide
O
5'
O HOH2C Base
OH P O
4' H H 1'
O H 3' 2'
H
OH OH
nucleotide
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O
5'
O P O CH2
Base
O
O H H
4' 1'
H 3' 2' H
O OH
O P O
O 5'
CH2
Base
O
4' H H 1'
H 3' 2' H
OH OH
Polynucleotide
• Based on the sugar present nucleic acids is classified to DNA and RNA
DNA RNA
Mainly occurs in the nucleus of the cellMainly occurs in the cytoplasm of
the cell
The sugar present is -D-2-deoxyribose Sugar present is -D-ribose
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STRUCTURE OF DNA
I) Primary structure
• It refers to the sequence in which 4-nitrogenous bases are attached to the sugar phosphate backbone
of nucleotide chain
II) Secondary structure
• DNA consist of 2 strands of polynucleotides coiled around each other in the form of a double helix.
• The two strands are antiparallel. ie their phospho diester linkage runs in opposite direction
• The bases are stacked inside the helix in a plane perpendicular to helical axis
• The two strands are held together by H-bonds
• The two strands are complimentary to each other. Because H-bonds are formed between specific
pairs of bases
• Adenine forms two H-bonds with Thymine, whereas Cytosine forms 3H bonds with Guanine
• Diameter of double helix is 2nm
• The helix repeats at aninterval of 3.4nm (1 complete turn)
• Total no of purine bases (A+G)=Total no. of pyrimidine bases (T+C)
Types of RNA
• RNA molecules are of 3 types and they perform different functions
They are:
• m-RNA messenger RNA
• r-RNA ribosomal RNA
• t-RNA transfer RNA
Transcription
• Copying of DNA sequence into m-RNA
Gene
DNA sequence that codes for a specific protein or polypeptide
Genetic code
• The relationship between nucleotide triplets and amino acids
Mutation
• Chemical change in a DNA that could lead to synthesis of protein with different amino acid sequence
• These changes are caused by radiations, chemical agents or viruses
• Most of these changes are automatically repaired by the special enzymes present in the cell
• Failures to repair by the enzyme system can cause a mutation
VITAMINS
• Vitamins are organic compounds required in diet in small amounts to perform specific biological
functions for normal maintenance of optimum growth and health of the organism
• Vitamins are classified into two groups depending on their solubility in water or fat
1) Fat soluble vitamins - A, D, E, K
2) Water soluble vitamins -Bcomplex and C
3) Vitamin H (presently B7) neither soluble in water or in fat
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• Water soluble vitamins should be regularly supplied in diet because they are readily excreted through
urine so they cannot be stored in body (except B12)
• The deficiency state of vitamins is called Avitaminoses
HORMONES
• Are chemical substances secreted by various ductless glands or endocrine glands
• Hormones play a very dynamic and vital role in different metabolic activities of the body
Steroid hormones
Eg: Adrenal cortex hormones like cortisol
and sex hormones like Estrogen, Progestrone,
Testosterone etc.
Hormones
Peptide hormones
Eg: Oxytocin,Vasopressin, Angiotensin, Insulin
Non-steroid hormones
Amine hormones
Eg: Adrenaline, Thyroxine
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CHAPTER - 00
CHEMISTRY IN EVERYDAY LIFE
Chemistry finds application in different fields of our life, like medicines, food, cleansing agents etc
Chemistry in Meidicines
Drugs and medicines
Chemicals of low molecular mass (100-500 u) that can interact with macromolecular targets
(biomolecules) and produce a biological response are called drugs. When the biological response is
therapeutic and useful, then the chemicals are called medicines and are used in diagnosis, prevention
and treatment of disease. Use of chemicals for therapeutic effect is called chemotherapy.
Medicines cure diseases, but they do not cause addiction and are of negligible toxicity and safe to use.
Drugs also cure diseases, but they are habit forming cause addiction and have serious side effects.
CLASSIFICATION OF DRUGS
I. On the basis of pharmacological effect
This classification is useful to doctors and provide them the whole range of drugs available for the
treatment of particular type of problem. Eg : Antipyretics,Analgesics etc
II. On the basis of drug action
This is based on the action of a drug on a particular biochemical process. Eg : Antacids, Antihistamins
etc.
III. On the basis of chemical structure
This classification provides the range of drugs sharing common structural features and often having
similar pharmacological activity. Eg : Sulpha drugs
IV. On the basis of molecular target
This classification provides the medicinal chemist, the drugs having the same mechanism of action
on targets.
Enzymes as drug targets
In biological catalysis, the main functions of enzymes are
i) To hold a substrate to carry out a reaction
ii) To provide functional group to attack the substrate
Drug Enzyme Interaction : Drugs can block the binding site of enzymes and prevent the binding of substrate,
or can inhibit the catalytic activity of enzyme. Such drugs are called enzyme inhibitors.
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1. Drugs compete with the natural substrate for their attachment on the active sites of enzymes. Such
drugs are called competitive Inhibitors.
ii. Some drugs do not bind to the enzyme’s active site. These bind to a different site of enzyme which
called the Allosteric site. This binding of inhibitor changes the shape of active site so that the substrate
cannot recognise it.
Receptors as drug targets
Receptors are proteins that are crucial in body’s communication process. They are embedded in cell
membrane and their active site projects out of the surface of the membrane and opens on the outside
region of cell membrane.
In the body, message between 2 neurons and that between neurons to muscles is communicated
through chemical messengers which are received at the binding site of receptors. To accomodate a
messenger the shape of the receptor site changes and these brings about the transfer of message
into the cell. Thus chemical messengers given messages to the cell, without entering the cell.
Antagonists : Drugs that bind to the receptor site and inhibits its natural function.
Agonists : Drugs that mimic or imitate the natural messengers by switching on the receptor.
Different classes of drugs
1. Anipyretics
Medicines used to reduce the body temperature
NHCOCH3 NHCOCH3
Eg :
OH OC2H5
p-hydroxy acetanilide (paracetamol) p-ethoxy acetanilide (phenacetin)
OCOCH3
COOH
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b) Antihistamines : Histamines causes allergic responses in body. They are potent vasodilator. It
contracts the smooth muscles in the bronchi and gut and relaxes the other muscles such as these in
the walls of fine blood vessels. It is also responsible for the nasal congestion associated with common
cold and allergy. The medicines used against these histamines are called antihistamines.
Eg : chloropheniramine, Bromopheniramine (Dimetapp), Terfenadine (seldane). Diphenyl hydramine
(Benadryl), Cetrizine, Avil (pheniramine maleate).
Histamines stimulate the secretion of pepsin and HCl in the stomach, so when antihistamines used as
antacid, they prevent the interaction of histamine with receptors present in the stomach wall and reduces
the secretion of acid.
When antihistamines used as antacids, and anti-allergic drugs they interfere with the function
of histamines, but they do not interfere with each other, because they act on different receptors.
3. Neurologically active drugs
i) Tranquillizers : They are substances used for the treatment of stress and even mild or severe
mental diseases. They reduce tension and anxiety. They act on central nervous system and are
hypnotics. They form an essential component of sleeping pills. They function by different mechanism.
For example : Noradrenaline is one of the neuro transmitter that plays a role in mood changes. If the
level of noradrenaline low then the person, suffers from depression. In that case anti-depressant drugs
are needed to counteract the effect of depression. These drugs inhibit the enzymes catalysing the
degradation of noradrenaline, as a result this important neuro-transmitter is slowly metabolised and
can activate its receptor for longer periods of time.
Eg : Iproniazid, phenelzine
Other examples of tranquillizers are
• Chlorodiazepoxide, Meprobamate - Mild tranquillizers suitable for relieving tension.
• Equanil - Used in controlling depression and hypertension
• Recerpine - An alkanoid extracted from the plant Rauwolfia serpentina (common name - Sarpagandha).,
is used to reduce hypertension
• Other eg : Valium, serotonin, Barbutaric acid derivatives like veronal, seconal, Luminal, Amytal, Nebutal
etc.
ii. Analgesics : To kill pain
The chemicals which are used to relief pain. They are of two type.
(a) Narcotic Analgesics : Which induces sleep. These are mainly used for the relief of post operative
pain, cardiac pain, pain of terminal cancer and in child birth. Eg : Cocaine, Pethadine, Morphine, Heroin,
Codeine etc. In medicinal doses these relieve pain and produces sleep but in higher doses it produces
stupor, coma, convulsions and death.
(b) Non-narcotic analgesics : Do not induce sleep
Eg : Paracetamol, Aspirin, Diclofenac sodium, Ibuprofen (Brufen), Oil of winter green (Methyl salicylate).
Naproxen
Importance of aspirin
Aspirin inhibits the synthesis of chemicals knowns as prostaglandins which stimulate inflammation in
the tissue and causes pain. These drugs are effective in relieving skeletal pain such as that due to
Arthritis. These are used as antipyretics to reduce fever and for preventing platelet coagulation. Because
of its anti blood clotting action aspirin finds use in prevention of heart-attacks.
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Limitation
The ester group in Aspirin get hydrolysed into acid group in stomach which causes ulcers or bleeding
in stomach. So Aspirin tablets can’t be consumed in empty stomach.
4. Antifertility drugs
Chemicals used to control pregnancy, these birth controll pills essentially contains a mixture of synthetic
estrogen and progesterone derivative. Eg : Norethindrone (progesterone derivative), Novestrolor
Ethynylestradiol (estrogen derivative used in combination with progesterone derivatives).
5. Anti microbials
Diseases in human beings and animals may be caused by a variety of micro-organism such as bacteria,
virus, fungi and other pathogens. An anti microbial tends to destroy or prevent development or inhibit
the pathogenic action of microbes such as bacteria, fungi, virus or other parasites.
a. Antibiotics : Substances which are produced from microorganism that can inhibit or even destroy
other micro-organisms. The first antibiotic is penicillin, discovered by Alexander Flemming from
Penicillium Notatum , presently penicillin is extracted from pencillium chrysogenum. Antibiotics have
either cidal (killing effect) or static (inhibitory effect) on microbes.
Bactericidal (killing) Bacteriostatic (inhibitory)
Penicillin Erythromycin
Tetracycline
Ofloxacin
Oriomycin (against eye disease)
Aminoglycosides Chloramphenicol
(against typhoid, pneumonia, acute fever, dysentery,
Meningitis, urinary infection
Chloramphenicol
NH CO CHCl2
O2N CH CH CH2OH
OH
The range of bacteria or other microbes, that are affected by a certain antibiotic is expressed as its
spectrum of action.
i. Broad spectrum antibiotics : The antibiotics which kill/inhibit the growth of wide range of gram +ve
and gram –ve bacteria. ie a single antibiotic can be used against a large no.of diseases.
Eg : Ampicillin, Amoxycillin (derivatives of penicillin), Vancomycin, Ofloxacin, Streptomycin,
Chloramphenicol, Tetracycline .
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ii. Narrow spectrum antibiotics : Effective against either gram +ve or gram -ve bacteria.
Eg- Penicllin-G
iii. Limited spectrum antibiotics : The antibiotic which are effective against a single organism or disease
Eg : Dysidazrine, is toxio towards, certain strains of cancer.
Streptomycin, a carbohydrate derivative is mainly used for the treatment of tuberculosis. It
can be used for the treatment of meningitis and pneumonia.
General structure of penicillin
O
H H CH3
S
R C NH CH3
N COOH
O
H
Penicillin R
Penicillin -G CH2
Penicillin - F CH 3 CH 2 CH CH CH 2
Penicillin - K CH3 (C H 2 ) 6
CH
Ampicillin
NH2
HO CH
Amoxycillin
NH2
The bacteria which retains the violet colour of crystal violet stain is gram (+ve) bacteria, and which
does not retain is gram (-ve) bacteria.
b. Antiseptic and Disinfectants
i. Antiseptics : Chemicals applied to the living tissues such as wounds, cuts, ulcers and diseased
skin surface, to kill or prevent the growth of micro-organisms
Examples
1) 0.2% phenol
2) Dettol, a mixture of chloroxylenol and terpineol
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Cl CH3
H3C
CH3
CH3 CH3
OH OH
3) 3% KMnO4
4) Iodoform CHI3
5) Tincture of iodine (2-3% I2 in alcohol - H2O mixture)
6) 30% w/v H2O2 100 volumes of H2O2 - perhydrol
7) Dyes like Gentian violet, Methylene blue
8) Colloidal silver (Argyrol) and very dilute aqueous solution of boric acid are used as weak antiseptic
for eye diseases.
9) Bithional - impart antiseptic properties to medicated soaps.
Cl OH OH Cl
Cl
Cl
OH
N2H
As
As NH2
HO
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Later, he prepared the first effective anti-bacterial agent - prontosil, which resembles in structures to
the compound salvarsan and when applied in the body, it converted to sulphanilamide.
NH2 SO2NH2
N
N
Prontosil
H2N
CHEMISTRY IN FOOD
Chemicals are used in food for their preservation enchancing their appear and adding nutritive values
in them. The important categories are
i) Preservatives : The chemicals which are used to stop the undesirable change in food caused by
microorganism like bacteria, fungi, mould etc. The following properties must be present in a preservative.
a. It should not react with food material
b. Its effect should be for longer period
c. It should not decrease the quality of food
d. It should not have harmful effect on body
Eg : Salt, sugar, vinegar, oil, salt of sorbic acid and propionic acid, sodium benzoate, sodium
metabisulphite, epoxide, p-hydroxy benzoate ester.
Sodium Benzoate undergoes metabolism in the body and excrete as hipuric acid (benzolyl glycin
through urine)
II. ARTIFICIAL SWEETNERS
Natural sweetners add more calories to the body but artificial sweetners do not. They excrete through
urine unchanged.
Example
1. Saccharin : The first popular artificial sweetner (1879). It is 550 times as sweet as cane sugar. It is
ortho sulphobenzimide.
CO
NH
. It is used in pan-masala, mouthwash tooth paste and cheap ice-creams, toffees,
SO2
drinks etc.
2. Aspartame : Methyl ester of dipeptide formed from aspartic acid and phenylalanine. 100 times as
sweet as cane-sugar. Unstable at cookng temperature, so its used in limited to soft-drinks and cold-
food.
3. Alitame : More stable than aspartame and 2000 times as sweet as cane sugar, so control of sweetness
of food is difficult.
4. Sucralose : Trichloro derivative of sucrose. 600 times as sweet as cane sugar. Appears and taste
like natural sugar.
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III. EDIBLE COLOURS (for reference only)
Carotene, Lycopene, Curcumin - Natural
Brilliant blue, Tartarazine, Sunset yellow - Artificial
IV. ANTIOXIDANTS
Used to prevent oxidation of fat, in food stuff. ie these are chemical substances which reduce the rate
of reaction with oxygen. Eg : N2, SO2, Vitamin E . BHT - Butylated Hydroxy Toluene, BHA - Butylated
Hydroxy Anisole.
V. FAT EMULSIFIERS AND STABILISING AGENTS
VI. FLAVOURS like mono-sodium glutamate MSG or Ajinomotto
VII. NUTRITIONAL SUPPLIMENT like minerals, vitamins and amino acids etc
CHEMISTRY IN CLEANSING AGENT
Soap and detergents
1. Soap : Soaps are sodium or potassium salt of long chain fatty acids like stearic acid, palmitic acid,
oleic acid etc. Glyceryl ester of these acids on alkaline hydrolysis gives soap (saponification- 2nd
order reaction)
CH2 O C C17H35
CH2 OH
O
Soap and glycerol is obtained in a colloidal form. From that soap is precipitaed by the addition of NaCl
solution (salting out of soap - app of common ion effect) and glycerol can be purified by distillation.
Types of soaps
Basicially all soaps are made by boiling fats or oils with suitable soluble hydroxide
i. Toilet soaps or soft soaps : Potassium salts of fatty acids, prepared by using good quality of oil and
normally free from excess alkali. Colour and perfumes are added to make these more attractive
ii. Floating soaps : These soaps float in water and prepared by beating tiny air-bublles before their
hardening.
iii. Transparent soaps : Made by dissolving the soap in ethanol and then evaporating the excess solvent
iv. Medicated soaps : Soft soaps containing substances of medicinal value
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v. Shaving soaps : Contains glycerol to prevent rapid drying. A gum called rosin is added to make
sodium rosinate which lathers well.
vi. Soap chips : Made by running, a thin sheet of melted soap into a cool cylinder and scrapping of soaps
in small broken pieces.
vii. Scouring soaps : Contain some soap and scouring or abrasive agent like finely divided sand and
builders like Na2CO3 and trisodium phosphate. Builders help the soap to act more rapidly.
viii. Laundry soaps : Contains filters like sodium rosinate, sodium silicate, borax and sodium carbonate.
Limitation of soap
Soaps can be used only in soft water, hard water contains Ca and Mg ion. When soaps are dissolved,
in hardwater these ions displaces sodium or potassium from their salt and forms insoluble calcium or
Mg salt of fatty acids. These insoluble salt separate as scum.
C 1 7 H 3 5 C O O 2 C a 2 N aC l
2 C 1 7 H 35 C O O N a C aC l 2
C a lc ium s tea ra te
(S cu m )
Detergents
Shows same properties like soap and can be used in both soft water and hard water, some of the
detergents give foam even in ice-cold water. Synthetic detergents mainly classified into 3 categories.
1. Anionic Detergents : These are Na salt of sulphoanted long chain alcohols or hydrocarbons. Alkyl
hydrogen sulphates, formed by treating long chain alcohol with conc.H2SO4 is neutralised with alkali to
form anionic detergents. In this the anionic part is involved in cleansing action. These are used for
household work and are also used in tooth pastes.
Eg : Sodium lauryl sulphate - CH 3 CH 2 11 OSO3 Na
2. Cationic Detergents : Quaternary Ammonium Salt of amines with acetates, chlorides or bromides
as anions. Cationic part possess a long hydrocarbon chain and a +ve charge on N-atom. These
detergents have germicidal properties and are expensive.
Eg: Cetyl Trimethyl Ammonium Bromide used in hair conditioners.
CH3
CH3
3. Non-ionic Detergents : Molecules of these detergents not contains any ions. These are esters with
high molecular mass. They contain polar group, which can form H-bond with water. Liquid dish washing
agents are this type. Mechanism of cleansing action of these detergents is same as that of soaps.
These also remove grease and oil by micelle formation.
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10