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Biomolecules: Chapter
Biomolecules: Chapter
Biomolecules
All living organisms are made of one or more cells which are considered as the smallest units of life.
Nearly all the compounds found in cells are composed of carbon, hydrogen, oxygen, nitrogen, phosphorus and
sulphur. The most abundant substance in living cells is water which amounts to approximately 70% mass of
the cells. Next come the compounds of carbon. Nearly all the carbon compounds found in living cells can be
placed into four classes:
(i) Carbohydrates
(ii) Amino acids and proteins,
(iii) Nucleic acids
(iv) Lipids
CARBOHYDRATES
Carbohydrates are mainly compounds of carbon, hydrogen and oxygen.
“A polyhydroxy compound that has an aldehydic or a ketonic functional group either free or as
hemiacetal or acetal.”
H O H OH
C C
CHOH CHOH
CHOH CHOH O
CHOH CHOH
CHOH CH
CH2OH CH2OH
Glucose (C 6H12O6) An internal hemiacetal
Aldehydic form
Carbohydrates with an aldehydic structure are known as aldoses and those with ketonic structure as ketoses.
All the carbohydrates should have at least one chiral c-atom.
CLASSIFICATION
The carbohydrates are divided into three major classes depending upon whether or not they undergo hydrolysis,
and if undergo hydrolysis, how many products are formed.
(i) Monosaccharides (Simple sugars)
They are single unit carbohydrates (polyhydroxy aldehydes or polyhydroxy ketones) which cannot be broken
into lower sugars upon hydrolysis.
[41]
[42] Chemistry–XII–Unit-VII
They have general formula, CnH2nOn. Glucose is the most important member of this class.
They are crystalline in nature, readily dissolve in water and are sweet in taste (sugars).
(ii) Oligosaccharides
They undergo hydrolysis yielding 2 to 9 molecules of monosaccharides. These are called oligosaccharides.
Majority of oligosaccharides are colourless crystalline solids, soluble in water and are sweet in taste. e.g.,
(a) The sucrose (C12H22O11) is a disaccharide as on hydrolysis it gives two monosaccharide units, i.e., one
molecule of glucose and one molecule of fructose.
H
C12 H 22 O11 H 2 O C 6 H12O 6 C 6 H12O 6
Sucrose Glucose Fructose
(b) Raffinose (C18H32O16) is a trisaccharide on hydrolysis, it gives three monosaccharide units.
C18H 32O16 2 H 2 O H C 6 H12O 6 C 6 H12O 6 C 6 H12O 6
Raffinose Glucose Fructose Galactose
CH2OH CH2OH
D(+) Glucose D(–) Fructose
Biomolecules [43]
(1) Carbohydrates that contain only acetals groups do not give positive test with Benedicts & Tollene
reagents are called non reducing sugars.
(2) All carbohydrates that contain hemiacetal groups giving positive test with Benedicts, Tollens reagents
are called reducing sugars.
4. Formation of glucosides :
When treated with methyl alcohol in presence of dry HCl gas, glucose yields monomethylether
which is actually a mixture of - and -forms indicating that one of the —OH group is different
from others. (It belongs to humi-acetal)
HCl
C6H11O5–OH+H OCH3 C6H11O5OCH3 + H2 O
- and -Methyl glucoside
H OCH3 CH3O H
C C
(CHOH)3 O (CHOH)3 O
CH CH
CH2OH CH2OH
-Methyl glucoside -Methyl glucoside
CH2OH(CHOH)4CHO+Ag2O CH2OH(CHOH)4COOH+2Ag
From Gluconic acid silver
Tollen's Reagent
(iii) Reaction with bromine water : Glucose is oxidised to gluconic acid (a monocarboxylic acid)
with bromine water or alkaline iodine solution or any mild oxidising agent.
CH 2 OH(CHOH) 4CHO [O]
Br2 /H 2 O
CH 2 OH(CHOH) 4COOH
Glucose Gluconic acid
(iv) Reaction with nitric acid : Nitric acid or any other strong oxidising agent converts glucose
to saccharic acid or glucaric acid ( a dicarboxylic acid) containing same number of carbon atoms.
CH 2OH(CHOH) 4 CHO 3[O] HNO
3 COOH(CHOH) 4 COOH H 2O
Glucose (C6) Saccharic acid
Biomolecules [45]
CN COOH
HOH HI
CH 2OH(CHOH) 4 CH CH 2 OH(CHOH) 4 CH Reduction CH 3 (CH 2 ) 4 CH 2 COOH
HCl
Heptanoic acid
OH OH
4. Reaction with hydroxylamine : Glucose forms an oxime with hydroxyl amine.
CH 2OH(CHOH) 4 CHO NH 2 OH CH 2 OH(CHOH) 4 CH NOH H 2 O
Glucose oxime
5. Reaction with phenylhydrazine (Fischer’s mechanism) : When warmed with excess of
phenylhydrazine, glucose first forms phenylhydrazone by condensation with —CHO group.
CHO H 2 NNHC 6 H 5 CH NNHC 6 H 5
Phenyl hydrazine
CHOH
CHO CHOH
CHO
warm
(CHOH)3 (CHOH)3
CH2OH CH2OH
Glucose Glucose phenyl hydrazone
(Yellow crystals)
The adjacent —CHOH group is then oxidised by a second molecule of phenyl hydrazine.
CH NNHC 6 H 5 CH NNHC 6 H 5
CHOH H 2 NNHC 6 H 5
C O C 6 H 5 NH 2 NH 3
(CHOH)3 (CHOH)3
CH2OH CH2OH
Keto compound of
glucose phenyl hydrazone
The resulting carbonyl compound reacts with a third molecule of phenyl hydrazine to yield glucosazone.
CH NNHC 6 H 5 CH NNHC 6 H 5
C O H 2 NNHC 6 H 5
C NNHC 6 H 5 H 2O
(CHOH)3 (CHOH)3
CH2OH CH2OH
Glucosazone
III. Miscellaneous Reactions
1. Fermentation : A solution of glucose is readily farmented by the enzyme, zymase, present in yeast to
form ethanol and carbon dioxide.
C 6 H12 O 6 Zymase
2C 2 H 5OH 2CO 2
Glucose Ethanol
2. Dehydration : When heated strongly or when treated with warm concentrated sulphuric acid, glucose
is dehydrated to give a black mass (sugar carbon).
C6 H12O 6 H
2SO 4
6C [6H 2O H 2SO 4 ]
[46] Chemistry–XII–Unit-VII
CH O CH OH CH2OH HO CH CH O
H C OH C OH C O HO C HO C H
Glucose Enol Fructose Enol Mannose
O H O H
C C
H C OH HO C H
HO C H HO C H
H C OH H C OH
H C OH H C OH
CH2OH CH2OH
D(+) Glucose D(+) Mannose
Epimers
C 6 H12O 6 Conc.HCl
CH 3COCH 2 CH 2COOH HCOOH H 2 O
Laevulic acid
On treatment with conc. HCl, glucose can also form hydroxymethyl furfural.
CH CH 3H 2 O
C 6 H12 O 6
HOCH2 C C CHO
O
Hydroxymethyl
furfural
Tests of glucose
When heated in a dry test tube, it melts, turns brown and finally black, giving a characteristic smell of burnt sugar.
When warmed with a little conc. H2SO4, it leaves a charred residue of carbon.
When it is boiled with dilute NaOH solution, it first turns yellow and then brown.
Molisch’s test : A drop or two of alcoholic solution of -naphthol is added to 2mL of glucose solution. 1mL
of concentrated H2SO4 is added carefully along the sides of the test tube. The formation of a violet ring, at the
junction of two liquids confirms the presence of a carbohydrate.
Silver mirror test : A mixture of glucose and ammonical silver nitrate is warmed in a test tube. Appearance
of silver mirror on the inner walls confirms glucose.
Fehling’s solution test : A little glucose is warmed with Fehling’s solution. A red precipitate of cuprous
oxide is formed.
Osazone formation : Glucose on heating with excess of phenyl hydrazine in acetic acid gives a yellow
crystalline compound.
Structure of Glucose
(A) Open chain structure : It is based on the following points:
Elemental analysis and molecular mass determination show that the molecular formula of glucose
is C6H12O6.
Glucose on complete reduction with HI and red phosphorus finally gives n-hexane. This indicates
that it contains a straight chain of six carbon atoms.
It reacts with acetic anhydride and forms penta-acetate derivative. This shows the presence of
five hydroxyl groups each linked to a separate carbon atom as the molecule is stable.
Glucose combines with hydroxyl amine to form a monoxime. It also combines with one mole of
HCN to form a cyanohydrin. These reactions indicate the presence of a carbonyl group, C O ,
in the molecule.
Mild oxidation of glucose with bromine water gives gluconic acid. This shows the presence of an
aldehyde group.
On the basis of above observations, the following open chain structure can be written for glucose.
OH OH OH OH OH H
H C *C *C *C *C C O
H H H H H
There are four asymmetric carbon atoms marked by asterisks (*) in the molecule. This representation
is incomplete, because a definite configuration to these asymmetric centres has not been assigned. The
configuration of D-glucose was proved by Emil Fischer. The structure of D-glucose as elucidated by
Emil Fischer is
H O
1
C
2
H C OH
3
HO C H
4
H C OH
5
H C OH
6
CH2OH
D-Glucose
[48] Chemistry–XII–Unit-VII
Evidence against open-chain structure : The open chain formula of glucose accounts for most of
the reactions satisfactorily but fails to explain the following:
Even though an aldehyde group is present, the glucose does not react with NaHSO 3 and NH3.
Glucose does not give the Schiff’s test for aldehydes.
Glucose penta-acetate does not react with hydroxyl-amine.
Two isomeric methyl glucosides ( and ) are obtained by heating glucose with methyl alcohol in
presence of dry HCl gas.
Glucose exists in two stereoisomeric forms ( and ) . -glucose with specific rotation +110°
10°
is obtained by crystallizing glucose from alcohol or acetic acid solution, whereas -glucose with
specific rotation +19.7° is obtained by crystallizing glucose from pyridine solution.
An aqueous solution of glucose shows mutarotation, i.e., its specific rotation gradually decreases
from +110° to +52.5° in case of -glucose and increases from +19.7° to +52.5° in case of -
glucose.
Note : These two & isomers are called anomers (isomers differ in configuration at c–1).
All these observations indicate that free aldehydic group is not present in the molecule.
Cyclic structure of glucose :
D-glucose exists in two optically active forms known as -D-glucose and -D-glucose.
-D-glucose has specific rotation of +110° and -D-glucose has specific rotation of +19.7°. The two
isomers are interconvertible in aqueous solution. The equilibrium rotation is +52.5°. The equilibrium
mixture has 36% -glucose, 64% -glucose. Glucose forms a stable cyclic hemiacetal (according to
Fischer) between —CHO group and the —OH group of the fifth carbon atom in pyranose structure. In
this process first carbon atom becomes asymmetric giving two isomers (I) and (II) which differ only in
the configuration of the first asymmetric carbon.
H O H OH HO H
1 1 1
C C C
2 2 2
CHOH CHOH CHOH
3 3 3
CHOH CHOH CHOH
4 4 4
CHOH CHOH CHOH
5 5 5
CHOH CH O CH O
6 6 6
CH2OH CH2OH CH2OH
D-Glucose -D-Glucose (I) -D-Glucose (II)
[]D = +52.5° []D = +110° []D = +19.7°
-Glucose open chain form -Glucose
0.02% 64%
Carbon-I in both configuration (I) and (II) is called an anomeric carbon atom. Due to anomeric carbon,
glucose exists in two forms. Both the forms have different physical properties and are called anomers.
Biomolecules [49]
The ring structure explains all the reactions of glucose. The objections against the open chain structure
of glucose have also been satisfactory explained, e.g.,
(i) - and - glucose on treatment with CH3OH in presence of dry HCl gas forms -, and -
methyl glucosides respectively.
H C OH H C OCH 3
H C OH H C OH
HO C H CH3 OH HO C H
O (Dry
HCl gas) O
H C OH H C OH
H C H C
CH2OH CH2OH
-D-Glucose (I) -D-Methyl glucoside
HO C H CH3O C H
H C OH H C OH
HO C H CH 3 OH HO C H
O (Dry
HCl gas) O
H C OH H C OH
H C H C
CH2OH CH2OH
-D-Glucose (II) -D-Methyl glucoside
(ii) No reaction with NH3 and NaHSO3 : The glucose ring is not very stable. It is easily broken up
by strong reagents like HCN, NH2OH and C6H5NHNH2, etc., to give the intermediate aldehyde
form, which reacts with them just like an aldehyde.
But weak reagents like NH3 and NaHSO3 are unable to open the chain and cannot react with it.
This explains the inability of glucose to form aldehyde ammonia and bisulphite compound.
(iii) It explains mutarotation : Ordinary glucose is -glucose, with a fresh aqueous solution has
specific rotation, [ ]D + 110°. On keeping the solution for some time; -glucose slowly changes
into an equilibrium mixture of -glucose (36%) and -glucose (64%) and the mixture has specific
rotation +52.5°.
Similarly a fresh aqueous solution of -glucose having specific rotation, [ ]D 19.7 , on (standing)
gradually changes into the same equilibrium mixture (having, specific rotation +52.7°). So an aqueous
solution of glucose shows a physical property, known as mutarotation, i.e., a change in the value
of specific rotation (muta = change; rotation = specific rotation) is called mutarotation.
(iv) Methods for determining the size of rings : Fischer and Tollen’s proposed that the ring or the
internal hemiacetal is formed between C1 and C4. It means the ring is Furan type or 5-membered
ring; this is called Furanose structure;
4 3
CH CH
5 2
CH CH
1
O
Furan
[50] Chemistry–XII–Unit-VII
However according to Haworth and Hirst the ring is formed between C 1 and C5. It means the ring
is Pyran type or 6-membered ring, this is called Pyranose structure.
CH2
4 3
5
HC CH
6 2
HC CH
1
O
Pyran
The two forms of D-glucose are also shown by Haworth projection formula which are given below:
6 6
CH2OH CH2OH
5 5
O O
H H H OH
4
H 1 4
H 1
OH H OH H
OH OH OH H
3 2 3 2
H OH H OH
-D-glucose -D-glucose
The above projection formulae show that the six membered ring is planar but actually the ring has a
chain structure similar to cyclohexane.
In Haworth formula all the OH groups on the right in Fischer’s formula are directed below the plane of
the ring while those on the left go above the plane. The terminal CH2OH projects above the plane of the
ring.
FRUCTOSE, FRUIT SUGAR C6H12O6, (KETO-HEXOSE)
It is present in abundance in fruits and hence is called fruit sugar. Since naturally occurring fructose is
laevorotatory, it is also known as laevulose.
Fructose is a keto-hexose. It is obtained along with glucose by hydrolysis of cane sugar with dilute H 2SO4.
H2SO4 (dil.)
C12 H22O11 + H2O C6H 12O 6 + C6H12O6
Cane sugar
Warm D-glucose D-Fructose
The solution having equal molecules of D-glucose and D-fructose is termed invert sugar and the process is
known as inversion.
Properties :
The anhydrous fructose is a colourless crystalline compound. It is soluble in water but insoluble in benzene
and ether. It is the sweetest of all sugars and its solution is laevorotatory. Like glucose, it also shows
mutarotation.
Fructose dissolved in aqueous base undergoes enolisation and series of keto-enol tautomensation results in
several products including D-glucose and D-manose. Hence it gives positive tollen’s and fehling test.
CH2OH
C=O
HO C H
H C OH
H C OH
CH2OH
D-Fructose
[]D = – 92º
Biomolecules [51]
HOH2C OH OH CH2OH
C C
HO C H HO C H
H C OH O H C OH O
H C OH H C OH
CH2 CH2
-D-Fructose - D-Fructose
[]D = – 21º []D = – 133º
Fructose gives reactions similar to glucose. The difference in properties is due to the fact that it contains a
ketonic group while glucose contains an aldehydic group.
Comparison of Glucose and Fructose
Property Glucose Fructose
1. Molecular formula C6H12O 6 C 6H12O 6
2. Nature Polyhydroxy aldehyde Polyhydroxy ketone
3. Melting point 146ºC 102ºC
4. Optical activity of natural form Dextrorotatory Laevorotatory
5. With ethyl alcohol Almost insoluble More soluble
Oxidation (a) No reaction
(a) Gluconic acid
6. (a) with bromine water (b) Mixture of glycollic acid, tartaric
(b) Saccharic acid (Glucaric acid)
(b) with nitric acid acid and trihydroxy glutaric acid.
7. Reduction Sorbitol Mixture of sorbitol and mannitol
Forms calcium glucosate, soluble Forms calcium fructosate, insoluble
8. Calcium hydroxide
in water in water
9. Molisch's reagent Forms a violet ring. Forms a violet ring
10. Fehling's solution Gives red precipitate Gives red precipitate
11. Tollen's reagent Forms silver mirror Forms silver mirror
12. Phenyl hydrazine Forms osazone Forms osazone
Resorcinol + HCl(dil.) (Selivanoff's Gives red or brown colour or
13. No colouration
test) precipitate
Freshly prepared ammonium
14. molybdate sol. + few drops of acetic Light blue colour Bluish green colour on heating
acid (Pinoff's test)
Alcoholic a-naphthol + HCl(conc.)
15. No colouration A purple colour (violet) on boiling
(Furfural test)
DISACCHARIDES
The disaccharides yield on hydrolysis two monosaccharides. Those disaccharides which yield two hexoses
on hydrolysis have a general formula C12H22O11. The hexoses obtained on hydrolysis may be same or different.
C12 H 22O11 C 6 H12O 6 C6 H12O 6
H2 O
H
Sucrose Glucose Fructose
Lactose H
2O
Glucose Galactose
H
Maltose
Glucose Glucose
H 2O
H
[52] Chemistry–XII–Unit-VII
6
CH2OH Glycoside
Glycoside linkage linkage
5
O
1
O 1
CH2OH 4 OH
H 2
1 2
C C OH 3
Or OH
(CHOH)3 (CHOH)2
O
5 6
HC O HC
5
O CH2OH O
5
6 6 2
CH2OH CH2OH OH
4 CH
1 2
OH
3
OH
Sucrose solution is dextrorotatory. Its specific rotation is +66.5ºC. But on hydrolysis, it becomes
laevorotatory. The specific rotation of D-glucose is +52º and of D-fructose is –92º. Therefore, the
net specific rotation of an equimolar mixture of D-glucose and D-fructose is.
52º 92º
20º
2
The process of hydrolysis of sucrose is thus termed as inversion of sugar and the hydrolysed
mixture having equivalent molar quantities of D-glucose and D-fructose is called invert sugar.
The enzyme that brings the inversion is named as invertase.
Biomolecules [53]
Reducing and non-reducing sugars : Those saccharides which reduce Fehling’s solution
and Tollen’s reagent are called reducing sugars and those which do not, non-reducing
sugars. Reducing sugars contain either -hydroxy aldehyde or -hydroxy ketone or they
contain cyclic hemiacetal or hemiketal or structures in equilibrium with open chain forms
having a free –CHO or >C=O group.
Reducing sugars : D-Glucose, D-Fructose, Maltose, Lactose
Non-reducing sugars : Sucrose, Starch, Cellulose
(C 6 H10O 5 ) n
(C 6 H10 O 5 )n1
C12 H 22O11
C 6 H 12 O 6
Starch Dextrin Maltose Glucose
Both n and n1, are unknown, but n is believed to be greater than n1.
When treated with enzyme, diastase, it yields maltose.
2(C 6 H10O 5 ) n nH 2O
nC12 H 22 O11
Starch Maltose
Starch solution gives a blue colour with a drop of iodine which disappears on heating to 75°C–80ºC and
reappears on cooling. Even the starch obtained from same source consists of two fractions (i)amylose
and (ii) amylopectin.
Amylose is a linear polymer while amylopectin is a highly branched polymer. Both are composed of -
D-glucose units linked by glycosidic linkages. The number of D-glucose units in amylose range from
60–300. It is soluble in hot water. Amylopectin consists of D-glucose units from 300–600. It is insoluble
in water.
OH OH OH
O O O O
OH OH OH n
-1, 4-Glycoside bonds Repeating monomer
Structure of amylose
[54] Chemistry–XII–Unit-VII
CH2OH CH2OH
O O
OH OH
O O
-1, 6-Glycoside bonds
OH n OH
O
Repeating monomer
CH2 CH2OH
CH2OH
O O O
OH OH OH
O O O O
OH n OH OH
-1, 4-Glycoside bonds Repeating monomer
Structure of amylopectin
B . Cellulose
It is found in all plants and so is the most abundant of all carbohydrates. Wood is about 50 % cellulose and the
rest is lignin. Cotton and paper are largely composed of cellulose.
Cellulose is insoluble in water and in most of the organic solvents. It decomposes on heating but does not
melt. It dissolves in ammonical copper hydroxide solution (Schwitzer’s reagent). Cellulose also dissolves in a
solution of zinc chloride in hydrochloric acid.
Biomolecules [55]
When it is treated with concentrated H2SO4 in cold, it slowly passes into solution. The solution when diluted
with water, a starch like substance amyloid is precipitated and is called parchment paper. When boiled with
dilute H2SO4, it is completely hydrolysed into D-glucose.
(C 6 H10O 5 ) n nH 2 O
nC 6 H12 O 6
Cellulose Glucose
Cellulose is a straight chain polysaccharide composed of D-glucose units which are joined by -glycosidic
linkages between C-1 of one glucose unit and C-4 of the next glucose unit. The number of D-glucose units in
cellulose ranges from 300 to 50000.
CH2OH H OH CH2OH H OH CH2OH H OH
H O H H O H H O H
H O OH H H O OH H H O OH H
O OH H O OH H O OH H O
H H H H H H H H H
O O O
H OH CH2OH H OH CH2OH H OH CH2OH
Structure of cellulose
Uses : Cellulose is used:
As such in the manufacture of cloth (cotton), canvas and gunny bags (jute) and paper (wood, bamboo,
straw, etc.)
In the form of cellulose nitrates for the manufacture of explosives (gun-powder), medicines, paints and
lacquers. The cellulose nitrates with camphor yield celluloid which is used in the manufacture of toys,
decorative articles and photographic films.
In the form of cellulose acetate for the manufacture of rayon (artificial silk) and plastics.
PROTEINS AND AMINO ACIDS
They are nitrogenous organic compounds of high molecular masses ranging from about 6000 to approximately
1,000,000. They are polymers made up of linking together in various combinations, a number of different
simple monomeric units called -amino acids. Proteins are synthesized by both plants and animals and upon
hydrolysis by enzymes yield amino acids.
A. Amino acids
An amino acid is a bifunctional organic molecule that contains both a carboxylic group—COOH, as well as an
amine group, —NH2. They are classified as acidic, basic or neutral according to number of amine and carboxyl
groups in a molecule. Neutral amino acids contain only one amine and one carboxylic group. They are further
classified according to the position of amine group in relation to carboxyl group into , , and amino
acids. Out of these amino acids are most important as they are building blocks of bio-proteins.
The general structure of the amino acids is represented as
Carboxyl group
H
R—C— COOH
NH 2 Amine group
Carbon atom
R may be alkyl, aryl or any other group.
The nature of R-group determines the properties of proteins. There are about 20 amino acids which make up
the bio-proteins. Out of these 10 amino acids (non-essential) are synthesised by our bodies and rest are
essential in the diet (essential amino acids) and supplied to our bodies by food which we take because they
cannot be synthesised or their synthesis in body in very less in the body. The -amino acids are classified
into the following four types:
[56] Chemistry–XII–Unit-VII
CH3 COOH
(Essential)
NH2
H
(ii) Amino acids with polar but neutral side chain : Examples are :
H
N
CH NH2
1. Tryptophan (Trp)
C—CH2CHCOOH
(Essential)
NH2
NH2
NH 2
NH2
CCH2CH
HC COOH
NH
3. Histidine (His)
N
CH
(Essential)
[58] Chemistry–XII–Unit-VII
Cl — CH 2COOH 2NH 3
H 2 NCH 2COOH NH 4Cl
-Chloro acetic acid Glycine
Br NH2
-Bromo propionic acid -Amino propionic acid
(Alanine)
C
ClCH 2 COOH 3 NH 3 50
H 2 NCH 2COONH 4 NH 4Cl
-Chloro acetic liquid Amm. salt of glycine
acid
The ammonium salt so obtained is boiled with copper carbonate and cooled when blue colour needles of
copper salt of glycine are obtained.
Boiled
2 H 2 N CH 2COONH 4 CuCO 3 (H 2 NCH 2 COO) 2 Cu (NH 4 ) 2 CO 3
Copper salt of glycine
It is now dissolved in water and H2S is passed till whole of the copper precipitates as copper sulphide
leaving glycine as the aqueous solution.
(ii) Gabriel phthalimide synthesis : -Halogenated acid or ester combines with potassium phthalimide.
The product on hydrolysis gives -amino acid.
CO CO
COOH
– KCl
NK ClCH 2 COOC 2 H 5
+
NCH 2COOC 2 H 5
2H 2 O
HCl
CO Chloro ethyl acetate
CO COOH
Pot. phthalimide Phthalic acid
+ CH2NH2COOH+C2H5OH
Glycine
(iii) Knoop synthesis : -Keto acid on treatment with ammonia forms an imine which on catalytic reduction
gives amino acid.
NH3
CH 3COCOOH CH 3C COOH H
2 /Pd
CH 3 CH COOH
or Na/C 2 H 5 OH
Pyruvic acid
NH NH2
Alanine
Biomolecules [59]
(iv) Strecker synthesis : An aldehyde reacts with HCN and ammonia or NH4CN and the product on
hydrolysis yields - amino acid.
H H H
H
R C O HCN
R C OH NH
3 R C NH 2 H
2O
R C NH 2
Aldehyde H
CN CN COOH
Cyanohydrin Aminonitrile -Amino acid
(v) From natural proteins : Natural proteins are hydrolysed with dil. HCl or H2SO4 at 250°C in an
autoclave when a mixture of -amino acids is obtained. This mixture is esterified and the various
esters are separated by fractional distillation. The esters are then hydrolysed into respective -amino
acids.
Properties :
(i) Amino acids are colourless, crystalline substances having sweet taste. They are soluble in water but
insoluble in organic solvents.
(ii) Except glycine, all the -amino acids are optically active and have an asymmetric carbon atom ( -
carbon atom).
(iii) Zwitter ion and isoelectric point : Since the —NH2 group is basic and —COOH group is acidic, in
neutral solution, it exists in an internal ionic form called a Zwitter ion where the proton of —COOH
group is transferred to the —NH2 group to form inner salt, also known as dipolar ion.
R R R
–
H 2 N CHCOOH H 2 N CH COO H
In water
H 3 N CH COO
-Amino acid Zwitter ion
(Dipolar ion)
The Zwitter ion is dipolar, charged but overall electrically neutral and contains both a positive and
negative charge.
Therefore, amino acids are amphoteric in nature. Depending on the pH of the solution, the amino acid
can donate or accept proton.
H O H O H O
H 3 N C C OH
H
H 3 N C C O
OH
H 2 N C C O
H2 O
(Proton removed)
R R R
Low pH (Acidic soln.) Zwitter ion (I) High pH (Basic soln.)
Positive form (II) Neutral form Negative form (III)
(Cation) (Anion)
When an ionised form of amino acid is placed in an electric field, it will migrate towards the opposite
electrode. Depending on the pH of the medium, following three things may happen:
In acidic solution (low pH), the positive ion moves towards cathode.
In basic solution (high pH), the negative ion moves towards anode.
The Zwitter ion does not move towards any of the electrodes.
The intermediate pH at which the amino acid shows no tendency to migrate towards any of
the electrodes and exists the equilibrium when placed in an electric field is known as isoelectric
point.
[60] Chemistry–XII–Unit-VII
LiAlH 4
NH2
4H
R—CH
CH2 OH
Amino alcohol
NH2
Limited NHCH3
RCH Alkylation
CH3 Br
RCH
COOH COOH
-Amino acid N-Methyl derivative
Acetylation
NHCOCH3
RCH
CH 3COCl
COOH
N-Acetyl derivative
Reactions shown due HNO 2
to amino group RCHOHCOOH
-Hydroxy acid
–
HCl N H3 C l
RCH
COOH
Salt formation
PCl5
NH2 (HCl)
RCH
COCl
Amino acid chloride
Action of heat : -Amino acids lose two molecules of water and form cyclic amides.
NH H OH OC NH—C
R– CH
+ CH R R– CH CH–R+2H2O
CO OH H HN C—NH
-Amino acid lose a molecule of ammonia per molecule of amino acid to yield , - unsaturated acids.
Heat CH CH=CHCOOH
CH3—CH—CH— COOH 3
(–NH3) Crotonic acid
NH2 H
-Amino butyric acid
- Amino acid and -amino acids undergo intramolecular dehydration to form cyclic amides called
Lactams.
CH2—CH2—CH2—CO Heat CH2—CH2—CH2—CO
(–H2O)
NH H H—O NH
-Amino butyric acid -Butyrolactam
CH2CH2CH2CH2CO Heat CH2CH2CH2CH2 CO
(–H2O) NH
NH H HO
-Amino valeric acid -Valerolactam
These lactams have stable five or six membered rings.
(B) Formation of proteins — Peptide bond : Proteins are formed by joining the carboxyl group of
one amino acid to the -amino group of another amino acid. The bond formed between two amino
acids by the elimination of a water molecule is called a peptide linkage.
—C OH + H— N— —C—N— + H2O
O H O H
Carboxyl group Amine group of Peptide bond
of one amino acid other amino acid
The product formed by linking amino acid molecules through peptide linkages, —CO—NH—, is called
a peptide.
O H O
O H O
H 2 N — CH — C — N — CH — C — OH (Dipeptide)
Peptide
linkage
R R
[62] Chemistry–XII–Unit-VII
O O
H 2 N — CH — C — — NH — CH — C — — NH — CH — COOH
R R´ n R´´
N.B. : Haemoglobin consists of 574 amino acid units in its molecule in a definite sequence. When only
one specific amino acid in the sequence is changed, it becomes a defective haemoglobin which loses its
specific property of carrying oxygen in blood stream and results in a disease called sickle cell anaemia.
Normal haemoglobin,
—Val—His—Leu—Thr—Pro—Glu—Glu—Lys—
Sickle cell haemoglobin,
—Val—His—Leu—Thr—Pro—Val—Glu—Lys—
Composition of proteins :
Composition of a protein varies with source. An approximate composition is as follows:
Carbon 50-53%; hydrogen 6-7%; oxygen 23-25%; nitrogen 16-17%; sulphur about 1%. Other elements may
also be present, e.g., phosphorus (in nucleoproteins), iodine (in thyroid proteins) and iron (in haemoglobin).
Structure of proteins
The primary structure of a protein refers to the number and sequence of the amino acids in its
polypeptide chains. The primary structure is represented beginning with the amino acid whose amino group
is free (the N-terminal end) and it forms the one end of the chain. Free carboxyl group (C-terminal end)
forms the other end of the chain.
O O
Left hand side Right hand side
–
H 2 N—CH—C—NH—CH—C—NH=CH—COOH
One end
(N-terminal end) R R´ R´´ Other end
(C-terminal end)
(R, R´, R´´... may be-same or different)
Primary structure tells us nothing about the shape or conformation of the molecule. The fixed configuration
of a polypeptide skeleton is referred to as the secondary structure of a protein. It gives information:
(a) about the manner in which the protein chain is folded and bent;
(b) about the nature of the bonds which stabilise this structure.
Secondary structure of proteins is mainly of two types:
(i) -Helix : This structure is formed when the chain of -amino acids coils as a right handed
screw (called -helix) because of the formation of hydrogen bonds between amide groups of
the same peptide chain, i.e., NH group in one unit is linked to carbonyl oxygen of the third unit by
hydrogen bonding. This hydrogen bonding between different units is responsible for holding helix in
a position.
Such proteins are elastic, i.e., they can be stretched. On stretching weak hydrogen bonds break up
and the peptide chain acts like a spring. The hydrogen bonds are reformed on releasing the tension.
Wool and hair have -helix structure.
Biomolecules [63]
Tertiary structure
e.g. Globular proteins possess tertiary structure.
Classification of proteins : Classification of proteins is made either on the basis of chemical composition
or molecular shape.
Simple proteins : Simple proteins are composed of chains of amino acid units only joined by peptide
linkages. These proteins on hydrolysis yield only mixture of amino acids. Examples are:
Egg albumin, serum globulins, glutelin in wheat, coryzenin in rice, tissue globulin, etc.
Conjugated proteins : The molecules of conjugated proteins are composed of simple proteins and
non-protein material. The non-protein material is called prosthetic group or cofactor. These proteins
on hydrolysis yield amino acids and non-protein material. Examples are:
Mucin in saliva (prosthetic group, carbohydrate), casein in milk (prosthetic group, phosphoric acid),
haemoglobin in blood (prosthetic group, iron pigment), etc.
(iv) Ninhydrin test : This test is given by all proteins. When a protein is boiled with a dilute solution of
ninhydrin, a violet colour is produced.
(v) Nitroprusside test : When sodium nitroprusside solution is added to proteins having —SH group, a
violet colour is developed.
O O OH
H
C OH C C
C + RCCOOH C = N —C
C OH C C
NH2
O O O
Ninhydrin Amino acid Violet Complex
(vi) Molisch’s test : This test is given by those proteins which contain carbohydrate residue. On adding a
few drops of alcoholic solution of -naphthol and concentrated sulphuric acid to the protein solution, a
violet ring is formed.
(vii) Hopkins-Cole test : On adding concentrated sulphuric acid down the side containing a solution of
protein and glyoxalic acid, a violet colour is developed.
Uses of proteins :
(i) As food : Proteins constitute as essential part of our food. Meat, eggs, fish, cheese provide proteins to
human beings.
(ii) In textile : Casein (a milk protein) is used in the manufacture of artificial wool and silk.
(iii) In the manufacture of amino acids : Amino acids, needed for medicinal use and feeding experiments,
are prepared by hydrolysis of proteins.
(iv) In industry : Gelatin (protein) is used in food products, capsules and photographic plates. Glue (protein)
is used as adhesive and in sizing paper. Leather is obtained by tanning the proteins of animal hides.
(v) In controlling body processes : Haemoglobin present in blood is responsible for carrying oxygen and
carbon dioxide. Hormones (proteins) control various body processes.
(vi) As enzymes : Enzymes are proteins produced by living systems and catalyse specific biological reactions.
NUCLEIC ACIDS
Nucleic acids are complex compounds of carbon, hydrogen, oxygen nitrogen and phosphorus. They play an
essential role in transmission of the hereditary characteristics and biosynthesis of proteins.
Two types of nucleic acids are found in biological systems, these are :
Deoxyribonucleic acid (DNA) and
Ribonucleic acid (RNA)
Nucleic acids, like proteins and carbohydrates, are polymers. The simple units that make up the
nucleic acids are called nucleotides composed of following three simple molecules.
1. Nitrogenous Base : These are heterocyclic organic compounds having two or more nitrogen atoms in
ring skeleton. They are called bases because the lone pairs of electrons on the nitrogen atoms make
them as Lewis bases. Their structure are given below :
(a) Pyrimidine derivatives
O OH NH 2 NH 2 O
6
6
CH3
HN N1
5
N N1 5
HN
or 2 ; or 2 ;
3 4 3 4
O N HO N O N HO N O N
H H H
Uracil (U) Cytosine (C) Cytosine (C) Thymine (T)
(RNA) (RNA) DNA
(DNA)
Biomolecules [67]
OH NH 2 NH2
CH3 CH3 CH2OH
6 5
N 1 N N
or 2 ; ;
3 4
HO N HO N HO N
5-Methyl Cytosine 5-Hydroxymethyl
cytosine
5 1´
CH2OH O OH CHOH
4 1
2´
C C CHOH O
or
3´
H H H H CHOH
4´
2
C CH
3C
5´
CH2OH
OH OH
Ribose
5
1´
CH2OH O OH CHOH
4 1
2´
C C CH2 O
or
3´
H H H H CHOH
4´
3 C
2
C CH
5´
CH2OH
OH H
Deoxyribose
Both differ only at carbon atom 2´ in the ring.
Phosphoric acid, H3PO4
Phosphoric acid forms esters to —OH groups of the sugars to bind nucleotide segments together. A molecule called
nucleoside is formed by condensing a molecule of the base with the appropriate pentose. (i.e., Base + Sugar).
[68] Chemistry–XII–Unit-VII
NH2
N
N
5´ 5´
CH2OH O OH CH2OH O N N
4´ 1´ 4´ 1´
NH 2 C C C C
N
N
Adenine + H H H H H H H H
H 2O
N N
C 3´ C2´ C 3´ C 2´
H
HO OH HO OH
Ribose Adenosine (Nucleoside)
A nucleotide results when the nucleoside combined with phosphoric acid mainly at carbon 5´ of the pentose.
(i.e., Base + Sugar + Phosphoric acid).
IIn nucleotide structures, the point of attachment with phosphoric acid may be 2´, 3´ or 5´ in the ribose
molecule and 3´ or 5´ in the deoxyribose molecule to the nucleoside structures.
This nucleotide is the building block of both DNA and RNA. The nucleic acids are condensation polymers
NH2
N
OH N
5´
HO—P—O—CH2 O N N
4´ 1´
O C C
H H H H
C 3´ C 2´
HO OH
Nucleotide-Adenosine 5´-phosphoric acid
of the nucleotide monomers and are formed by the creation of an ester linkage from phosphoric residue on
one nucleotide to the hydroxy group on carbon 3´ in the pentose of the second nucleotide. The result is a very
long chain possessing upto a billion or so nucleotides units in DNA.
HO—P—O—Sugar—Base
O O
HO—P—O—Sugar—Base
O O
HO—P—O—Sugar—Base
O O
HO—P—O—Sugar—Base
O O
Biomolecules [69]
Nitrogenous bases, combining with pentose sugars and a phosphate group, form eight types of nucleotide
molecules, four for DNA and four for RNA. These are listed ahead :
Sugar phosphate chains
Base pairs
S G C
S
P
P
T A
3´´ Direction
S S
5´ 3´Direction
P
P
S C G S
P P
S C G S
P P
S A T S
P P
O O
P CYTOSINE
HO O N—H O N
CH2O
5´
1´ N O
4´ N H—N 2´ 3´
2´
N N
3´ 1´
O H—N 4´
O O O H C 5´
H 2
P O HO
H
HO O
H P
N N—H O CH3
O O
5´
CH2O N 2´ 3´
1´
4´ N H—N
Hydrogen
2´
N bonds N 1´
4´
3´
H O O 5´
O H 2C
ADENINE THYMINE
O HO
Nucleotides P
O O
CHEMICAL STRUCTURES OF BASE-PAIRS AND SUGAR-PHOSPHATE CHAINS
[70] Chemistry–XII–Unit-VII
RNA Nucleotides
Base + Ribose (Nucleoside) + Phosphoric acid Nucleotide
1. Adenine + Ribose (Adenosine) + Phosphoric acid Adenylic acid
2. Guanine + Ribose (Guanosine) + Phosphoric acid Guanylic acid
3. Cytosine + Ribose (Cytidine) + Phosphoric acid Cytidylic acid
4. Uracil + Ribose (Uridine) + Phosphoric acid Uridylic acid
DNA Nucleotides
1. Adenine + Deoxy ribose sugar + Phosphate Adenosine phosphate
2. Guanine + Deoxy ribose sugar + Phosphate Guanosine phosphate
3. Cytosine + Deoxy ribose sugar + Phosphate Cytosine phosphate
4. Thymine + Deoxy ribose sugar + Phosphate Thymidine phosphate
Structure
The sequence of bases along the DNA and RNA chain establishes its primary structure which controls the
specific properties of the nucleic acid. An RNA molecule is usually a single chain of ribose-containing
nucleotides. DNA molecule is a long and highly complex, spirally twisted, double helix, ladder like structure.
The two polynucleotide chains or strands are linked up by hydrogen bonding between the nitrogenous base
molecules of their nucleotide monomers. Adenine (purine) always links with thymine (pyrimidine) with the
help of two hydrogen bonds and guanine (purine) with cytosine (pyrimidine) with the help of three hydrogen
bonds. Hence, the two strands extend in opposite directions, i.e., are antiparallel and complimentary. The
following fundamental relationship exist:
Biomolecules [71]
N.B: Thymine combines only with deoxyribose sugar and uracil only with ribose sugar. Other bases can
combine with either of the two sugars.
The double helix is 20 Å. It completes a spiral at every 10 nucleotide pairs at a length of 34 Å. Sequences of
monomers (nucleotides) may present innumerable variations. Evidently, innumerable varities of DNA exist in
the organism.
(i) Replication : The genetic information for the cell is contained in the sequence of the bases A, T, G and
C (adenine, thymine, guanine and cytosine) in the DNA molecule. The sequence of bases in one chain
of the double helix controls the sequence in other chain. The two chains fit together like a hand and a
glove. They separate and about the hand is formed a new glove, and inside the glove is formed a new
hand. Thus, the pattern is preserved in the two new molecules of DNA.
[In one strand of DNA has the sequence ATGCTTGA, then the sequence of complimentary strand will
be TACGAACT.]
(ii) Synthesis of proteins : The DNA contains the genetic code and directs protein synthesis through
RNA. The double helix of DNA partially uncoils and about the individual strands are formed chains of
RNA. The new chains contain ribose instead of deoxyribose and the base sequence is different which
is determined by DNA, i.e., opposite each adenine of DNA, there appears on RNA , a uracil; opposite
guanine, cytosine; opposite thymine, adenine, opposite cytosine, guanine. Thus, AATCAGTT on DNA
becomes UUAGUCAA on RNA.
One kind of RNA, called messenger RNA, carries a message to the ribosome, where protein synthesis
actually takes place. At the ribosome, messenger RNA calls up a series of transport RNA molecules,
each of which is loaded with a particular amino acid. The order in which the transport RNA molecules
are called (– the sequence in which the amino acids are arranged to form the protein chain) depends
upon the sequence of bases along the messenger RNA chain. Thus, GAU is the code for aspartic acid;
UUU, phenyl alanine; GUG, valine. There are 64 -three letter code words (codons) and only 20 odd
amino acids, so that more than one codon can call the same amino acid.
The DNA sequence that codes for a specific protein is called a Gene and thus every protein in a cell
has a corresponding gene. The relation between the nucleotide triplets and the amino acids is called the
Genetic Code. Nirenberg, Hollay and Khorana presented the Genetic Code for which they were
awarded Noble Prize in 1968. The following Genetic Code has been accepted :
[72] Chemistry–XII–Unit-VII
Nonsense codons : These do not code for any amino acid. For these codons no tRNA is available.
Therefore tRNA will not bring amino acid. In this way protein synthesis is terminated. They serve to
terminate peptide chains.
Mutation : A mutation is a chemical or physical change that alters the sequence of bases in DNA
molecule. Anything that causes mutation is called mutagen. A mutation results from ultraviolet light,
ionisation radiations, chemicals or viruses. The changes in sequence of bases in DNA are repaired by
special enzymes in the cell. If it is not, the protein produced has no biological activity and the cell dies.
These mutations often prove harmful and give rise to symptoms that cause diseases. Sickle-cell anaemia
is one such example. Such disease is passed on from one generation to the next generation.
LIPIDS
Lipids are constituents of plants and tissues which are insoluble in water but soluble in organic solvents such
as chloroform, carbon tetrachloride, ether or benzene. Lipids are mainly made of carbon, hydrogen and
oxygen. Sometimes small amounts of phosphorus, nitrogen and sulphur are also present. Lipids serve as
energy reserve for use in metabolism and as a major structural material in cell membranes for regulating the
activities of cell and tissues.
Simple lipids are esters of glycerol with long chain monocarboxylic acids which can be saturated or unsaturated.
These are generally called glycerides of fats and oils. Waxes are esters of fatty acids with certain alcohols,
not glycerol. Fats and oils have biological importance but waxes have no value as these are not digested. The
functions of triglycerides are the following :
(i) They are energy reserves in the cells and tissues of living system. When digested, triglycerides are
hydrolysed to fatty acids and glycerol.
Biomolecules [73]
(ii) Catabolism of fatty acids form acetyl-coenzyme-A. Most of the energy of fatty acids is converted into
ATP.
(iii) Acetyl co-enzyme is the starting material for the synthesis of many compounds.
(iv) Fats deposited beneath the skin and around the internal organs minimise loss of body heat and also act
as cushions to absorb mechanical impacts.
Phospholipids : These are polar lipids and like the fats, are esters of glycerol. In this case, however, only
two fatty acid molecules are esterified to glycerol, at the first and second carbon atom. The remaining end
position of the glycerol is esterified to a molecule of phosphoric acid, which in turn is also esterified to another
alcohol. This gives a general structure.
R´´
O
O=P—O—CH2 O
OH CH—O—C—R´
CH2O—C—R
O
Phosphate : The phosphate group forms a polar end, i.e., hydrophilic (water-attracting) and the two fatty
acid chains constitute the non-polar tail, i.e., hydrophobic (water repelling).
The common examples of phospholipids are lecithins and cephalines which are found in brain, nerve cells and
liver of animals. These are also found in egg yolks, yeast, soyabeans and other foods.
Lecithins are derivatives of choline chloride, HOCH2CH2 N (CH3)3Cl— and cephalines are derivatives of
ethanolamine, HOCH2CH2NH2.
CH2COOC15C31 CH2COOC15C31
O– O–
Lecithin Cephalin
Lecithin contains a quaternary nitrogen whereas cephalin contains only primary nitrogen.
The above mentioned lipids are mainly straight chain compounds. There is a third class of lipids which are not
straight chain compounds. They are called Sterols. The sterols are composed of fused hydrocarbon rings
and a long hydrocarbon side chain. Cholestrol is most important compound of this class and is found in
animals only. It exists either free or as ester with a fatty acid. Cholestrol is also the precursor of hormones.
Cholestrol is a part of animal cell membrane and is used to synthesise steroid hormones, vitamin-D and bile
salts.
Waxes : These are simple lipids and they are esters of long chain fatty acids and monohydric alcohols.
General formula of waxes can be given as RCOOR´
Waxes are found as protective layers on fruits, leaves and animals. They are insoluble in water, flexible and
non-reactive.
[74] Chemistry–XII–Unit-VII
Hormones : These are the chemicals which are secreted by ductless glands and transported to different
parts of the body by the blood stream where they control different physiological action of the body.
Classification of hormones : On the basis of structure and composition, hormones are classified into
following types :
1. Steroid hormones : These hormones are composed to steroid nucleus having following structure :
These are mostly secreted by testes and adrenal cortex of males and hence, called as adrenal cortex
hormones or sex hormones. Examples of these hormones are androgens testosterone and dihydro
testosterone. These hormones are stimulant of male sex characteristics.
In females, sex hormones are estrogens. These hormones are produced in ovaries.
2. Polypeptides hormones : These hormones are polypeptide (protein). These hormones are secreted
by posterior lobe of the pitutary gland. Examples of such hormones are oxytocin, insulin and vasopressin.
3. Amine hormones : These are water soluble hormones containing amino groups. These are derived
from amino acids. Examples of such hormones are : thyroxine and adrenaline.
Food
The substances which supply the raw materials for various life processes alongwith energy as to control body
functions and maintain its growth are known as food.
The food, which we take, can broadly be divided into following groups on the basis of their functions:
(i) Energy yielding food - Carbohydrates, fats
(ii) Body building food - Proteins, minerals
(iii) Protective food - Vitamins, minerals
[76] Chemistry–XII–Unit-VII
EXERCISES
LEVEL – I BIOMOLECULES
Choose the appropriate answer:
1. Aqueous solution of carbohydrate with 2 drops of 6. Human digestive system does not hydrolyse:
alcoholic solution of -naphthol and H2SO4 gives (1) Starch (2) Maltose
a ring at the junction. The colour of the ring is
(3) Glycogen (4) Cellulose
(1) Yellow (2) Green 7. Glucose is used
(3) Violet (4) Red (1) In manufacture of vitamin C
2. Which of the following is the structure of D-xylose: (2) As preservative
CHO CHO (3) In the manufacture of alcohol
HO H HO H (4) All of these
H OH HO H 8. Maltose is made up of
(1) H OH (2) H OH (1) -D glucose (2) and -D glucose
CH 2OH CH 2OH (3) Glucose and fructose (4) Fructose only
CHO CHO 9. Glycogen and amylopectin have
H OH H OH (1) Same structure
HO H H OH (2) Similar structure but differ in branching of
(3) H (4) H glucose chain
OH OH
(3) Similar structure but differ in their solubility in
CH2OH CH 2OH water
3. Direct conversion of starch into glucose may be (4) Same structure but they are stored in different
carried out by parts of the body
(1) Fermentation with diastase 10. Which statement about ribose is incorrect:
(2) Fermentation with zymase (1) A polyhydroxy compound
(3) Heating it with dil. HCl (2) An aldehyde sugar
(4) Fermentation with maltase (3) Has six carbon atoms
4. Identify the product ‘Z’ in the following series of (4) Exhibits optical activity
reactions: 11. The function of fat in the body is to act:
C6H12O6(glucose) HCN (1) Reserve food
X H
2O HI
Y Z
(1) Hexanoic acid (2) As thermal insulator and to protect the body
from loss of heat
(2) -methyl caproic acid
(3) To absorb and carrying vitamin A and D in
(3) Heptanoic acid the body
(4) None of these (4) All of these
5. Glycogen is 12. Detergents are usually made from products
(1) A polysaccharide found in both animals and obtained by cracking of petroleum like:
plants (1) Chloroalkanes
(2) A polysaccharide found in plants (2) Sulphur compounds of benzene
(3) A polysaccharide found in animals (3) H2S
(4) A polysaccharide found in honey (4) Polyethylene derivatives
Biomolecules — MCQs [77]
13. Fats and oil are formed from (3) To catalyse biochemical process
(1) Glycerol and long chain unsaturated acid only (4) Form the structural material of tissues
(2) Glycerol and long chain saturated acids only 19. The pH of blood is (approximately)
(3) Glycerol and long chain saturated and (1) 7.4 (2) 5.2
unsaturated acids (3) 11.3 (4) 9.6
(4) Ethylene glycol and long chain saturated and 20. Disease caused by under secretion of adrenal
unsaturated acids cortex is
14. The unused fat present in the body is (1) Cretinism (2) Dwarfism
(1) Converted into carbohydrates (3) Sterility (4) Addison’s disease
(2) Removed as waste from the body 21. Respiration ultimately results in
(3) Reconverted into animal fat and stored in (1) CO2 + O2 (2) Glucose + O2
different parts of the body (3) Glucose + CO2 (4) CO2 + H2O
(4) Easily destroyed by certain enzymes present 22. Amino acids usually exist in the form of Zwitter
in the body ions which consist of
15. Which statement about fats and oils is correct: (1) The basic group – NH2 and the acidic group
(1) They may be edible as well as inedible – COOH
(2) Vegetable oils are different than essential oils (2) The acid group – N H 3 and the basic group
(3) Soyabean oil, corn oil, olive oil, etc., are edible oil CO 2
(4) All of these (3) The acid group – C O 2 and the basic group
16. Which of the following statements are not true NH 3
(1) Fat and oils are stored source of energy (4) No acidic or basic group
(2) They provide more energy than proteins or 23. The enzyme pepsin hydrolyses
carbohydrates (1) Proteins to amino acids
(3) They help in absorbing the vitamins A and D (2) Fats to fatty acids
(4) Fats are soluble in water (3) Glucose to ethyl alcohol
17. Soap molecule has two parts, a polar part and a (4) Polysaccharides to monosaccharides
non-polar part. When soap is added to water: 24. Proteins give:
(1) Both parts dissolve in water (1) A violet colour with alkaline CuSO4 solution
(2) Non-polar part dissolves in water (2) Form a purple colour on boiling with dilute
(3) Polar part dissolves in water ninhydrin solution
(4) Both parts remain undissolved in water and (3) Yellow colour on boiling with HNO3
form a hydrocarbon layer
18. The main role of oils and fats as constituents in (4) All of these
our food is to 25. Keratin, a structural protein is present in
(1) Act as stored source of energy (1) Hair (2) Skin
(2) To meet immediate energy needs of the body (3) Wool (4) All of these
bGbGbGb
[78] Chemistry–XII–Unit-VII
LEVEL – II BIOMOLECULES
Choose the appropriate answer:
1. Which one of the following is first member of (1) Ketones are oxidised by Fehling solution
monosaccharides?
(2) Keto sugars undergo transformation into
O aldose sugars in the presence of Fehling’s
|| solution
(1) HOH 2 C C CH 2 OH
(3) (1) and (2) both are correct
(2) HOH2C – CHOH – CHO
(4) Both (1) and (2) are incorrect
(3) HOH2C – CHOH – CHOH – CHO
8. In the given reactions :
O
|| Glucose + 3C6H5NHNH2 H /
Osazone + A
(4) HOH 2 C CHOH C CH 2OH +B
2. Which one of the following is reducing sugar? (A) and (B) are :
(1) Starch (2) Cellulose (1) C6H5NH2 and NH3
(3) Glycogen (4) Fructose (2) C6H5NH2 and NH2OH
3. In the given structure (I) there are four chiral (3) C6H5NH–NHOH and NH3
carbons. Hence this structure will have how many (4) NH2OH and HOH
stereoisomers? 9. Which of the following gives violet colour with
HOH 2 C–CHOH– C HOH–CHOH –CHOH– conc. HCl?
CHO (1) Fructose (2) Glucose
(1) 16 (2) 8 (3) Maltose (4) Starch
(3) 32 (4) 4 10. If specific rotation of glucose solution is 52º and
4. D glucose and D glucose are : fructose solution is –92° then what will be specific
rotation of invert sugar?
(1) Anomers (2) 2-Epimers
(1) –20° (2) +20°
(3) 3-Epimers (4) Enantiomers
(3) –72° (4) +72°
5. Which of the following statements are correct :
11. Starch is
(1) All the three forms of glucose are
(1) pure single compound
interconvertible in aqueous solution
(2) mixture of two polysaccharides of glucose
(2) Amount of all the three forms of glucose are
same in aqueous solution (3) mixture of two polysaccharides, one is
polysaccharide of glucose and other is fructose
(3) Interconversion of one form into other two
forms are not the cause of mutarotation (4) Dextrin
12. In the given reaction
(4) glucose is more stable than glucose
6. Which of the following compound will not show Cellulose (
i ) CS2 / NaO
[X]
( ii ) HCl / HOH
mutarotation?
[X] will be
(1) Methyl- D- glucopyranoiside (1) Guncotton (2) Rayon
(2) D (+) glucospyranose (3) Cellulose xanthate (4) Cellulose acetate
(3) D (+) glucopyranose 13. Which one of the following is heterogeneous
(4) D (+) galactopyranose polysaccharide :
7. Fructose is ketose sugar even then it gives red (1) Starch (2) Dxtrin
precipitate with Fehling solution because : (3) Glycogen (4) Gum arabic
Biomolecules — MCQs [79]
14. The reaction of glucose with methyl alcohol in the 20. Tertiary structure of protein contains which type
presence of dryl HCl shows that it is a : of forces :
(1) Polyhydroxy aldehyde (1) Electrostatic forces only
(2) Polyhydroxy alcohol (2) Electrostatic as well as hydrogen bonds
(3) Cyclic hemiacetal (3) Electrostatic, hydrogen bonds and Van der
(4) Polyhydroxy ketone Waal forces
15. In the given reaction : (4) Electrostatic, hydrogen bonds, Van der Waal
forces, dipole-dipole attractions and disulphide
Glucose + n-Phenylhydrazine
Osazone cross-linkage
The value of n is : 21. Aldenosine is an example of :
(1) Three (2) Two
(1) Nucleotide (2) Nucleoside
(3) One (4) Four
(3) Purine base (4) Pyrimidine base
16. Hydrolysis of sucrose is called :
22. Structure of DNA molecule is :
(1) Saponification (2) Inversion
(1) Single stranded (2) Linear
(3) Hydration (4) All of these (3) Branched (4) Double stranded
17. The number of polypeptide chains present in 23. Deficiency of vitamin-C causes :
haemoglobin is :
(1) Scurvy (2) Rickets
(1) Two (2) Four
(3) Pernicious anaemia (4) All of these
(3) Nine (4) 50
24. Genetic material of the cell is :
18. Secondary structure of proteins is due to :
(1) Lipids (2) Nucleic acid
(1) Peptide bond (2) Hydrogen bond
(3) Proteins (4) Carbohydrate
(3) Covalent bond (4) Co-ordinate bond
25. The enzyme which converts glucose and fructose
19. A pigment protein in animals is : into ethyl alcohol is
(1) Chlorophyll (2) Carotenoid (1) Diastase (2) Invertase
(3) Haemoglobin (4) Blood (3) Zymase (4) Maltase
bGbGbGb
[80] Chemistry–XII–Unit-VII
SELF ASSESSMENT
Choose the appropriate answer:
1. The number of atoms in the ring structure of The end product would be useful as:
pyranoses are (1) A soap (2) A fertilizer
Carbon Oxygen (3) An explosive (4) A detergent
(1) 5 1 10. Spermaceti is commonly used in
(2) 4 2
(1) Fermentation of cane sugar
(3) 4 1
(2) Preparation of acetic acid
(4) 3 2
(3) Birth control
2. To become a carbohydrate, a compound must
contain atleast (4) Cosmetics and soaps
(1) 6 carbons (2) 3 carbons 11. Digestion of fat in intestine is aided by
(3) 4 carbons (4) 2 carbons (1) Diffusion (2) Protection
3. Which of the following monosaccharide is pentose: (3) Peptization (4) Emulsification
(1) Glucose (2) Fructose 12. The energy change produced by the combustion
(3) Arabinose (4) Galactose of foods is called the ‘calorific value’. The best
4. Sugars are characterised by the preparation of calorific value is given by
osazone derivatives. Which sugar have identical (1) Proteins (2) Fats
osazones (3) Carohydrates (4) Vitamins
(1) Glucose and lactose 13. The purine base present in RNA is
(2) Glucose and fructose (1) Guanine (2) Thymine
(3) Glucose and arabinose (3) Cytosine (4) Uracil
(4) Glucose and maltose 14. The vitamin which is water soluble and antioxidant
5. The number of asymmetric carbon atoms in is:
fructose are : (1) Vitamin E (2) Vitamin D
(1) 2 (2) 3 (3) Vitamin C (4) Vitamin B1
(3) 4 (4) 5 15. Vitamin B1 is chemically known as:
6. Milk sugar is (a disaccharide): (1) Ascorbic acid (2) Riboflavin
(1) Sucrose (2) Lactose (3) Pyridoxine (4) Thiamine
(3) Fructose (4) Glucose
16. Deficiency of vitamin E causes:
7. Fats and oils belong to the class of
(1) Sterility (2) Rickets
(1) Alcohols (2) Acids
(3) Beri-Beri (4) Scurvy
(3) Esters (4) Hydrocarbons
17. Which statement is not correct for an enzyme:
8. Sodium dodecyl benzene sulphonate is used as a
(1) It acts as a biocatalyst
(1) Pesticide (2) Soap
(3) Fertilizer (4) Detergent (2) Its aqueous solution is colloidal
9. In the following reaction sequence, (3) It can catalyse any chemical reaction
R–CH=CH2+H2 SO4 RCH–CH3 (4) Its catalytic efficiency is temperature
dependent
SO4H 18. The function of enzymes in the living system is to:
NaOH
(1) Transport oxygen
(where R=C14H29) R–CH–CH3 (2) Provide immunity
(3) Catalyse Biochemical reaction
SO4–Na+ (4) Provide energy
Biomolecules — MCQs [81]
19. Which of the following element is responsible for (2) Starches into sugar
oxidation of water to O2 in biological processes: (3) Glucose into glycogen
(1) Fe (2) Mn (4) -amino acids into proteins
(3) Cu (4) Mo 26. The human body does not produce
20. Adenosine is an example of: (1) Enzymes (2) DNA
(1) Nucleotide (2) Nucleoside (3) Vitamins (4) Hormones
(3) Purine base (4) Pyrimidine base 27. During the process of digestion, the protein present
21. The digestion of fats in the intestines is aided by: in food materials are hydrolysed to amino acids.
(1) Diffusion (2) Protection The two enzymes involved in the process
(3) Peptization (4) Emulsification Proteins
Enzyme(A)
Polypeptides
22. An example of natural biopolymer is
Enzyme(B)
Aminoacids
(1) Teflon (2) Nylon-6,6 are respectively
(3) Rubber (4) DNA (1) Invertase and Zymase
23. Enzymes, in the living systems: (2) Amylase and Maltase
(1) Provide energy (2) Provide immunity (3) Diastase and Lipase
(3) Transport oxygen (4) Pepsin and Trypsin
(4) Catalyse biochemical process 28. Which one of the following is a peptide hormone?
24. In nucleic acids, the sequence is: (1) Adrenaline (2) Glucagon
(1) Phosphate-base-sugar (3) Testosterone (4) Thyroxin
(2) Sugar-base-phosphate 29. The pyrimidine -bases present in DNA are
(3) Base-sugar-phosphate (1) Cytosine and thymine
(4) Base-phosphate-sugar (2) Cytosine and uracil
25. Enzyme trypsin converts: (3) Cytosine and adenine
(1) Proteins into -amino acids (4) Cytosine and guanine
bGbGbGb
[82] Chemistry–XI–Unit-II
ANSWERS (BIOMOLECULES)
LEVEL - I
1. (3) 6. (4) 11. (4) 16. (4) 21. (4)
LEVEL - II
SELF ASSESSMENT
1. (1) 7. (3) 13. (4) 19. (1) 25. (1)
2. (2) 8. (4) 14. (3) 20. (2) 26. (2)
3. (3) 9. (4) 15. (4) 21. (4) 27. (4)
4. (2) 10. (4) 16. (1) 22. (4) 28. (2)
5. (2) 11. (4) 17. (3) 23. (4) 29. (1)
6. (2) 12. (2) 18. (3) 24. (3)