II PUC Chemistry Unit 14

Unit 14: Biomolecules
 Biochemistry: Branch of chemistry which deals with what goes on chemically within
a living system.
Carbohydrates
 Carbohydrates may be defined as optically active polyhydroxy aldehydes or ketones
or the compounds which produce such units on hydrolysis.
 Primarily produced by plants and form a very large group of naturally occurring
organic compounds
 Examples: cane sugar, glucose, starch, etc.
 General formula, Cx(H2O)y , and were considered as hydrates of carbon from where
the name carbohydrate was derived.
 For example, the molecular formula of glucose (C6H12O6) fits into this general
formula, C6(H2O)6 .
 Exception: Acetic acid (CH3COOH) fits into this general formula, C2(H2O)2 but is not
a carbohydrate.
 Rhamnose, C6H12O5 is a carbohydrate but does not fit in this definition.
 Some of the carbohydrates, which are sweet in taste, are also called sugars.
 The most common sugar, used in our homes is named as sucrose whereas the sugar
present in milk is known as lactose. Carbohydrates are also called saccharides (Greek:
sakcharon means sugar).
Classification of Carbohydrates
Based on hydrolysis:
(i) Monosaccharides: A carbohydrate that cannot be hydrolysed further to give simpler

unit of polyhydroxy aldehyde or ketone is called a monosaccharide.
Examples: glucose, fructose, ribose, etc.
(ii) Oligosaccharides: Carbohydrates that yield two to ten monosaccharide units, on

hydrolysis, are called oligosaccharides.
 They are further classified as disaccharides, trisaccharides, tetrasaccharides, etc.,
depending upon the number of monosaccharides, they provide on hydrolysis.
 Amongst these the most common are disaccharides.
 The two monosaccharide units obtained on hydrolysis of a disaccharide may be same
or different. For example, one molecule of sucrose on hydrolysis gives one molecule
of glucose and one molecule of fructose whereas maltose gives two molecules of only
glucose.
(iii) Polysaccharides: Carbohydrates which yield a large number of monosaccharide

units on hydrolysis are called polysaccharides.
Examples: starch, cellulose, glycogen, gums, etc. Polysaccharides are not sweet in taste,
hence they are also called non-sugars.
The carbohydrates may also be classified as either reducing or non reducing sugars.
 All those carbohydrates which reduce Fehling’s solution and Tollens’ reagent are
referred to as reducing sugars. All monosaccharides whether aldose or ketose are
reducing sugars. (Contains α hydroxy aldehyde or α hydroxyl keto group)
 Carbohydrate which do not reduce Fehling’s solution and Tollens’ reagent are referred
to as non-reducing sugars. (these do not contain free aldehyde or ketonic group)
Example: Sucrose
Monosaccharides
Monosaccharides are further classified on the basis of number of carbon atoms and the
functional group present in them.
 If a monosaccharide contains an aldehyde group, it is known as an aldose and if it
contains a keto group, it is known as a ketose. Number of carbon atoms constituting
the monosaccharide is also introduced in the name.
Glucose
 Glucose occurs freely in nature as well as in the combined form.
 It is present in sweet fruits and honey.
 Ripe grapes also contain glucose in large amounts.
Preparation
1. From sucrose (Cane sugar): If sucrose is boiled with dilute HCl or H2SO4 in alcoholic
solution, glucose and fructose are obtained in equal amounts.
2. From starch: Commercially glucose is obtained by hydrolysis of starch by boiling it

with dilute H2SO4 at 393K under pressure.
Structure of Glucose
Glucose is an aldohexose and is also known as dextrose. It is the monomer of many of the
larger carbohydrates, namely starch, cellulose. It is probably the most abundant organic
compound on earth. It was assigned the structure given below on the basis of the
following evidences:
1. Its molecular formula was found to be C6H12O6.
2. On prolonged heating with HI, it forms n-hexane, suggesting that all the six carbon
atoms are linked in a straight chain.
3. Glucose reacts with hydroxylamine to form an oxime and adds a molecule of hydrogen
cyanide to give cyanohydrin. These reactions confirm the presence of a carbonyl group
(>C = O) in glucose.
4. Glucose gets oxidised to six carbon carboxylic acid (gluconic acid) on reaction with a
mild oxidising agent like bromine water. This indicates that the carbonyl group is present
as an aldehydic group.
5. Acetylation of glucose with acetic anhydride gives glucose pentaacetate which

confirms the presence of five –OH groups. Since it exists as a stable compound, five –OH
groups should be attached to different carbon atoms.
6. On oxidation with nitric acid, glucose as well as gluconic acid both yield a
dicarboxylic acid, saccharic acid. This indicates the presence of a primary alcoholic (–
OH) group in glucose.
Cyclic Structure of Glucose

The structure (I) of glucose explained most of its properties but the following reactions
and facts could not be explained by this structure.
1. Despite having the aldehyde group, glucose does not give Schiff’s test and it does not
form the hydrogensulphite addition product with NaHSO3.
2. The pentaacetate of glucose does not react with hydroxylamine indicating the absence
of free —CHO group.
3. Glucose is found to exist in two different crystalline forms which are named as α and
β. The α-form of glucose (m.p. 419 K) is obtained by crystallisation from concentrated
solution of glucose at 303 K while the β-form (m.p. 423 K) is obtained by crystallisation
from hot and saturated aqueous solution at 371 K. This behaviour could not be explained
by the open chain structure for glucose.
 It was proposed that one of the —OH groups may add to the —CHO group and
form a cyclic hemiacetal structure.
 It was found that glucose forms a six-membered ring in which —OH at C-5 is
involved in ring formation. This explains the absence of —CHO group and also
existence of glucose in two forms as shown below. These two cyclic forms exist in
equilibrium with open chain structure.
The two cyclic hemiacetal forms of glucose differ only in the configuration of the
hydroxyl group at C1, called anomeric carbon (the aldehyde carbon before cyclisation).
Such isomers, i.e., α-form and β-form, are called anomers. The six membered cyclic
structure of glucose is called pyranose structure (α– or β–), in analogy with pyran. Pyran
is a cyclic organic compound with one oxygen atom and five carbon atoms in the ring.
The cyclic structure of glucose is more correctly represented by Haworth structure as
given below.

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Unit 14: Biomolecules

(i) Monosaccharides: A carbohydrate that cannot be hydrolysed further to give simpler

(ii) Oligosaccharides: Carbohydrates that yield two to ten monosaccharide units, on

(iii) Polysaccharides: Carbohydrates which yield a large number of monosaccharide

2. From starch: Commercially glucose is obtained by hydrolysis of starch by boiling it

1. Its molecular formula was found to be C6H12O6.

5. Acetylation of glucose with acetic anhydride gives glucose pentaacetate which

Cyclic Structure of Glucose

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