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Carbohydrate

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Carbohydrates|ISC Chemistry
Project|Biswajit Das
By All About Chemistry - September 6, 2021  600  0

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Carbohydrates are a type of macronutrient

that provide energy to the body. They can
be simple sugars or complex molecules like
starches and fibers.

We will provide some interesting Chemistry

Research topics , this will help you to gain more
knowledge about different spheres of chemistry.
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Introduction
The carbohydrates may be defined as optically
active polyhydroxy aldehydes or ketones or the
compounds which produce such units on hydrolysis.

Carbohydrates are primarily produced by plants and

form a very large group of naturally ccurring organic
compounds. Some common examples of
carbohydrates are cane sugar, glucose, starch, etc.
Most of them have a 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.
But all the compounds which fit into this formula
may not be classified as carbohydrates. For example
acetic acid (CH3COOH) fits into this general formula,
C2(H2O)2but is not a carbohydrate. Similarly,
rhamnose, C6H12O5 is a carbohydrate but does not
fit in this definition. A large number of their
reactions have shown that they contain specific
functional groups.

Carbohydrates are probably the most abundant and

widespread organic substances in nature, and they
are essential constituents of all living things.
Carbohydrates are formed by
green plants from carbon dioxide and water during
the process of photosynthesis. Carbohydrates serve
as energy sources and as essential structural
components in organisms; in addition, part of the
structure of nucleic acids, which contain genetic
information, consists of carbohydrate.

Classi.cation of
Carbohydrates
Carbohydrates are classified on the basis of their
behaviour on hydrolysis. They have been broadly
divided into following three groups.
(i) Monosaccharides: A carbohydrate that cannot be
hydrolysed further to give simpler unit of
polyhydroxy aldehyde or ketone is called a
monosaccharide. About 20 monosaccharides are
known to occur in nature. Some common examples
are 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. Some common examples
are 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 nonreducing 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.

Although a number of classification schemes have

been devised for carbohydrates, the division into
four major groups—
monosaccharides, disaccharides, oligosaccharides,
and polysaccharides—used here is among the most
common. Most monosaccharides, or simple sugars,
are found in grapes, other fruits, and honey.
Although they can contain from three to nine carbon
atoms, the most common representatives consist of
five or six joined together to form a
chainlike molecule. Three of the most important
simple sugars—glucose (also known as dextrose,
grape sugar, and corn sugar), fructose (fruit sugar),
and galactose—have the same molecular formula,
(C6H12O6), but, because their atoms have different
structural arrangements, the sugars have different
characteristics; i.e., they are isomers.

Slight changes in structural arrangements are

detectable by living things and influence the
biological significance of isomeric compounds. It is
known, for example, that the degree of sweetness of
various sugars differs according to the arrangement
of the hydroxyl groups (―OH) that compose part of
the molecular structure. A direct correlation that
may exist between taste and any specific structural
arrangement, however, has not yet been
established; that is, it is not yet possible to predict
the taste of a sugar by knowing its specific
structural arrangement. The energy in the chemical
bonds of glucose indirectly supplies most living
things with a major part of the energy that is
necessary for them to carry on their activities.
Galactose, which is rarely found as a simple sugar,
is usually combined with other simple sugars in
order to form larger molecules.

Two molecules of a simple sugar that are linked to

each other form a disaccharide, or double sugar.
The disaccharide sucrose, or table sugar, consists of
one molecule of glucose and one molecule of
fructose; the most familiar sources of sucrose
are sugar beets and cane sugar. Milk sugar,
or lactose, and maltose are also disaccharides.
Before the energy in disaccharides can be utilized by
living things, the molecules must be broken down
into their respective
monosaccharides. Oligosaccharides, which consist of
three to six monosaccharide units, are rather
infrequently found in natural sources, although a
few plant derivatives have been identified.

Polysaccharides (the term means many sugars)

represent most of the structural and energy-reserve
carbohydrates found in nature. Large molecules that
may consist of as many as 10,000 monosaccharide
units linked together, polysaccharides vary
considerably in size, in structural complexity, and in
sugar content; several hundred distinct types have
thus far been identified. Cellulose, the principal
structural component of plants, is a
complex polysaccharide comprising many glucose
units linked together; it is the most common
polysaccharide. The starch found in plants and
the glycogen found in animals also are complex
glucose polysaccharides. Starch (from the Old
English word stercan, meaning “to stiffen”) is found
mostly in seeds, roots, and stems, where it is stored
as an available energy source for plants. Plant
starch may be processed into foods such as bread,
or it may be consumed directly—as in potatoes, for
instance. Glycogen, which consists of branching
chains of glucose molecules, is formed in
the liver and muscles of higher animals and is stored
as an energy source.

The generic nomenclature ending for the

monosaccharides is -ose; thus, the
term pentose (pent = five) is used for
monosaccharides containing five carbon atoms,
and hexose (hex = six) is used for those containing
six. In addition, because the monosaccharides
contain a chemically reactive group that is either
an aldehyde group or a keto group, they are
frequently referred to as aldopentoses or
ketopentoses or aldohexoses or ketohexoses.
The aldehyde group can occur at position 1 of an
aldopentose, and the keto group can occur at a
further position (e.g., 2) within a ketohexose.
Glucose is an aldohexose—i.e., it contains six carbon
atoms, and the chemically reactive group is an
aldehyde group.

Preparation of Glucose
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 393 K 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.

Biological signi.cance
The importance of carbohydrates to living things can
hardly be overemphasized. The energy stores of
most animals and plants are both carbohydrate
and lipid in nature; carbohydrates are generally
available as an immediate energy source, whereas
lipids act as a long-term energy resource and tend
to be utilized at a slower rate. Glucose, the
prevalent uncombined, or free, sugar circulating in
the blood of higher animals, is essential
to cell function. The proper regulation
of glucose metabolism is of paramount importance
to survival.

The ability of ruminants, such as cattle, sheep, and

goats, to convert the polysaccharides present in
grass and similar feeds into protein provides a major
source of protein for humans. A number of medically
important antibiotics, such as streptomycin, are
carbohydrate derivatives. The cellulose in plants is
used to manufacture paper, wood for construction,
and fabrics.

Role in the biosphere

The essential process in the biosphere, the portion
of Earth in which life can occur, that has permitted
the evolution of life as it now exists is the
conversion by green plants of carbon dioxide from
the atmosphere into carbohydrates, using light
energy from the Sun. This process,
called photosynthesis, results in both the release
of oxygen gas into the atmosphere and the
transformation of light energy into the chemical
energy of carbohydrates. The energy stored by
plants during the formation of carbohydrates is used
by animals to carry out mechanical work and to
perform biosynthetic activities.

Role in human nutrition

The total caloric, or energy, requirement for an
individual depends on age, occupation, and other
factors but generally ranges between 2,000 and
4,000 calories per 24-hour period (one calorie, as
this term is used in nutrition, is the amount of heat
necessary to raise the temperature of 1,000 grams
of water from 15 to 16 °C [59 to 61 °F]; in
other contexts this amount of heat is called the
kilocalorie). Carbohydrate that can be used by
humans produces four calories per gram as opposed
to nine calories per gram of fat and four per gram
of protein. In areas of the world where nutrition is
marginal, a high proportion (approximately one to
two pounds) of an individual’s daily energy
requirement may be supplied by carbohydrate, with
most of the remainder coming from a variety of fat
sources.

Although carbohydrates may compose as much as

80 percent of the total caloric intake in the human
diet, for a given diet, the proportion of starch to
total carbohydrate is quite variable, depending upon
the prevailing customs. In East Asia and in areas of
Africa, for example, where rice or tubers such as
manioc provide a major food source, starch may
account for as much as 80 percent of the total
carbohydrate intake. In a typical Western diet, 33 to
50 percent of the caloric intake is in the form of
carbohydrate. Approximately half (i.e., 17 to 25
percent) is represented by starch; another third
by table sugar (sucrose) and milk sugar (lactose);
and smaller percentages by monosaccharides such
as glucose and fructose, which are common in fruits,
honey, syrups, and certain vegetables such
as artichokes, onions, and sugar beets. The small
remainder consists of bulk, or indigestible
carbohydrate, which comprises primarily the
cellulosic outer covering of seeds and the stalks and
leaves of vegetables. (See also nutrition.)

Role in energy storage

Starches, the major plant-energy-reserve
polysaccharides used by humans, are stored in
plants in the form of nearly spherical granules that
vary in diameter from about three to 100
micrometres (about 0.0001 to 0.004 inch). Most
plant starches consist of a mixture of two
components: amylose and amylopectin. The glucose
molecules composing amylose have a straight-chain,
or linear, structure. Amylopectin has a branched-
chain structure and is a somewhat more
compact molecule. Several thousand glucose units
may be present in a single starch molecule. (In the
diagram, each small circle represents one glucose
molecule.)

In addition to granules, many plants have large

numbers of specialized cells, called parenchymatous
cells, the principal function of which is the storage of
starch; examples of plants with these cells include
root vegetables and tubers. The starch content of
plants varies considerably; the highest
concentrations are found in seeds and
in cereal grains, which contain up to 80 percent of
their total carbohydrate as starch. The amylose and
amylopectin components of starch occur in variable
proportions; most plant species store approximately
25 percent of their starch as amylose and 75
percent as amylopectin. This proportion can be
altered, however, by selective-breeding techniques,
and some varieties of corn have been developed
that produce up to 70 percent of their starch as
amylose, which is more easily digested by humans
than is amylopectin.

In addition to the starches, some plants (e.g.,

the Jerusalem artichoke and the leaves of certain
grasses, particularly rye grass) form storage
polysaccharides composed of fructose units rather
than glucose. Although the fructose polysaccharides
can be broken down and used to prepare syrups,
they cannot be digested by higher animals.

Starches are not formed by animals; instead, they

form a closely related polysaccharide, glycogen.
Virtually all vertebrate and invertebrate animal cells,
as well as those of numerous fungi and protozoans,
contain some glycogen; particularly high
concentrations of this substance are found in the
liver and muscle cells of higher animals. The overall
structure of glycogen, which is a highly branched
molecule consisting of glucose units, has a
superficial resemblance to that of the amylopectin
component of starch, although the structural details
of glycogen are significantly different. Under
conditions of stress or muscular activity in animals,
glycogen is rapidly broken down to glucose, which is
subsequently used as an energy source. In this
manner, glycogen acts as an immediate
carbohydrate reserve. Furthermore, the amount of
glycogen present at any given time, especially in the
liver, directly reflects an animal’s nutritional state.
When adequate food supplies are available, both
glycogen and fat reserves of the body increase, but
when food supplies decrease or when the food
intake falls below the minimum energy
requirements, the glycogen reserves are depleted
quite rapidly, while those of fat are used at a slower
rate.

Role in plant and animal

structure
Whereas starches and glycogen represent the major
reserve polysaccharides of living things, most of the
carbohydrate found in nature occurs as structural
components in the cell walls of plants.
Carbohydrates in plant cell walls generally consist of
several distinct layers, one of which contains a
higher concentration of cellulose than the others.
The physical and chemical properties of cellulose are
strikingly different from those of the amylose
component of starch.

In most plants, the cell wall is about 0.5 micrometre

thick and contains a mixture of cellulose, pentose-
containing polysaccharides (pentosans), and an inert
(chemically unreactive) plastic-like material
called lignin. The amounts of cellulose and pentosan
may vary; most plants contain between 40 and 60
percent cellulose, although higher amounts are
present in the cotton fibre.

Polysaccharides also function as major structural

components in animals. Chitin, which is similar to
cellulose, is found in insects and other arthropods.
Other complex polysaccharides predominate in the
structural tissues of higher animals.

Structural arrangements and

properties
Studies by German chemist Emil Fischer in the late
19th century showed that carbohydrates, such as
fructose and glucose, with the
same molecular formulas but with different
structural arrangements and properties (i.e.,
isomers) can be formed by relatively simple
variations of their spatial, or geometric,
arrangements. This type of isomerism, which is
called stereoisomerism, exists in all biological
systems. Among carbohydrates, the simplest
example is provided by the three-carbon aldose
sugar glyceraldehyde. There is no way by which the
structures of the two isomers of glyceraldehyde,
which can be distinguished by the so-called Fischer
projection formulas, can be made identical,
excluding breaking and reforming the linkages, or
bonds, of the hydrogen (―H) and hydroxyl (―OH)
groups attached to the carbon at position 2. The
isomers are, in fact, mirror images akin to right and
left hands; the term enantiomorphism is frequently
employed for such isomerism. The chemical and
physical properties of enantiomers are identical
except for the property of optical rotation.

Optical rotation is the rotation of the plane of

polarized light. Polarized light is light that has been
separated into two beams that vibrate at right
angles to each other; solutions of substances that
rotate the plane of polarization are said to be
optically active, and the degree of rotation is called
the optical rotation of the solution. In the case of
the isomers of glyceraldehyde, the magnitudes of
the optical rotation are the same, but the direction
in which the light is rotated—generally designated
as plus, or d for dextrorotatory (to the right), or as
minus, or l for levorotatory (to the left)—is opposite;
i.e., a solution of D-(d)-glyceraldehyde causes the
plane of polarized light to rotate to the right, and a
solution of L-(l)-glyceraldehyde rotates the plane of
polarized light to the left.

Con.guration
Molecules, such as the isomers of glyceraldehyde—
the atoms of which can have different structural
arrangements—are known as asymmetrical
molecules. The number of possible structural
arrangements for an
asymmetrical molecule depends on the number of
centres of asymmetry; i.e., for n (any given number
of) centres of asymmetry, 2n different isomers of a
molecule are possible. An asymmetrical centre in
the case of carbon is defined as a carbon atom to
which four different groups are attached. In the
three-carbon aldose sugar, glyceraldehyde, the
asymmetrical centre is located at the central carbon
atom.

The position of the hydroxyl group (―OH) attached

to the central carbon atom—i.e., whether ―OH
projects from the left or the right—determines
whether the molecule rotates the plane of polarized
light to the left or to the right. Since glyceraldehyde
has one asymmetrical centre, n is one in the
relationship 2n, and there thus are two possible
glyceraldehyde isomers. Sugars containing four
carbon atoms have two asymmetrical centres;
hence, there are four possible isomers (22).
Similarly, sugars with five carbon atoms have three
asymmetrical centres and thus have eight possible
isomers (23). Keto sugars have one less
asymmetrical centre for a given number of carbon
atoms than do aldehyde sugars.

A convention of nomenclature, devised in 1906,

states that the form of glyceraldehyde whose
asymmetrical carbon atom has a hydroxyl group
projecting to the right is designated as of the D-
configuration; that form, whose asymmetrical
carbon atom has a hydroxyl group projecting to the
left, is designated as L. All sugars that can be
derived from D-glyceraldehyde—i.e., hydroxyl group
attached to the asymmetrical carbon atom most
remote from the aldehyde or keto end of the
molecule projects to the right—are said to be of
the D-configuration; those sugars derived from L-
glyceraldehyde are said to be of the L-configuration.

The configurational notation D or L is independent of

the sign of the optical rotation of a sugar in solution.
It is common, therefore, to designate both, as, for
example, D-(l)-fructose or D-(d)-glucose; i.e., both
have a D-configuration at the centre of asymmetry
most remote from the aldehyde end (in glucose) or
keto end (in fructose) of the molecule,
but fructose is levorotatory and glucose is
dextrorotatory—hence the latter has been given
the alternative name dextrose. Although the initial
assignments

of configuration for the glyceraldehydes were made

on purely arbitrary grounds, studies that were
carried out nearly half a century later established
them as correct in an absolute spatial sense. In
biological systems, only the D or L form may be
utilized.

When more than one asymmetrical centre is present

in a molecule, as is the case with sugars having four
or more carbon atoms, a series of DL pairs exists,
and they are functionally, physically, and chemically
distinct. Thus, although D-xylose and D-lyxose both
have five carbon atoms and are of the D-
configuration, the spatial arrangement of the
asymmetrical centres (at carbon atoms 2, 3, and 4)
is such that they are not mirror images.

Hemiacetal and hemiketal