EKO UNIVERSITY OF MEDICINE AND

HEALTH SCIENCES, IJANIKIN, LAGOS

FACULTY OF BASIC MEDICAL SCIENCES

DEPARTMENT OF CHEMISTRY

COURSE TITLE: GENERAL CHEMISTRY

COURSE CODE: CHM 102 (PART B)

(LECTURE NOTE )
BY
R.A AZEEZ (B.Sc Chem, M.Sc Pharm chem)
Carbohydrates I
Topical Outline of Coverage
Definition of Carbohydrates
Importance
Classification
Physical properties
Stereoisomerism
Optical activity
Chemical properties
Test: Benedict’s Test
Oxidation reaction
Reduction to alcohol
Introduction
Carbohydrates are naturally occurring
compounds found in both plants and animals and
are essential to life. Plants through a process
known as photosynthesis, convert carbon dioxide
and water to carbohydrates, mainly starch,
cellulose and sugars. Cellulose is the main
building block of rigid cell walls and woody
tissue in plants.
While starch, is the chief storage form of
carbohydrates for later use as a food or
energy source.
Some plants like cane sugar and sugar beets
produces sucrose, ordinary table sugar.
The word carbohydrates arose because the
molecular formulas of these compounds can
be expressed as hydrates of carbon.
For example, Glucose has the molecular formula
C6H12O6 (where carbon (C) hydrogen (H) and oxygen
(O) are in the ration 1:2:1) which may be written as
C6(H2O)6, which implies, carbon with six water
molecules (carbo from carbon and hydrate from water,
together they form the word carbohydrate). The study of
the chemistry of carbohydrates has over the years gone
beyond this formula, but the old name “carbohydrate”
still persists.
Intended learning outcomes (ILOs)
At the end of this unit, students should be able to;
· Define carbohydrates
· State the importance of carbohydrates
· Identify the different classes of carbohydrates.
· State the physical and chemical properties of
carbohydrates.
Definition of Carbohydrates
Carbohydrates are polyhydroxy aldehyde, polyhydroxy
ketones or compounds that can be hydrolyzed to them.
Chemically, carbohydrates are organic molecules in
which carbon, hydrogen, and oxygen bond together in
the ratio 1:2:1 (Cx(H2O)y, (where x and y are whole
numbers that differ depending on the specific
carbohydrate).
Importance of Carbohydrates
The carbohydrates are a major source of metabolic energy,
both for plants and for animals that depend on plants for
food. Aside from the sugars and starches that meet this
vital nutritional role, carbohydrates also serve as a
structural material (cellulose), a component of the energy
transport compound ATP, recognition sites on cell
surfaces, and one of three essential components of DNA
and RNA.
Cellulose is the main building block of rigid
cell walls and woody tissue in plants. While
starch, is the chief storage form of
carbohydrates for later use as a food or energy
source. Some plants like cane sugar and sugar
beets produces sucrose, ordinary table sugar.
Another sugar, glucose is an essential component
of blood. Two other sugars, ribose and 2-
deoxyribose, are components of the genetic
materials RNA and DNA. Other carbohydrates are
important components of coenzymes, antibiotics,
cartilage, the shells of crustaceans, bacterial cell
walls and mammalian cell membranes.
Classification of Carbohydrates
Carbohydrates can be classified into four different
groups; monosaccharides, disaccharides,
oligosaccharides and polysaccharides. A carbohydrate
that cannot be hydrolysed to two simpler molecules is
called a monosaccharide. A carbohydrate that can be
hydrolysed to two monosaccharide molecules is called a
disaccharide.
A carbohydrate that can be hydrolysed to between 3 and
10 monosaccharide molecules is called an
oligosaccharide. Polysaccharides are very complex in
structure. They can be regarded as high polymers of
monosaccharides and yield many molecules of these on
hydrolysis. The most common ones have the general
formula (C6H10O5)n e.g starch (n= 2,400 – 30,000),
cellulose (n= 2,000 – 4,000) and glycogen (n= 5,000 –
10,000). On complete hydrolysis, they all give glucose.
Figure: Classification of Carbohydrates
How are the three classes of carbohydrates
related to each other through hydrolysis?
A monosaccharide may be further classified. If it contains an
aldehyde group, it is known as an aldose; if it contains a ketone
group, it is known as a ketose. Depending upon the number of
carbon atoms it contains, a monosaccharide is known as a triose,
tetrose, pentose and hexose.

These two systems of classification are often combined.

An aldohexose, for example is a six-carbon monosaccharide
containing an aldehyde group; a ketopentose is five-carbon
monosaccharide containing a keto group.
 Glucose is an aldohexose (a six-
carbon aldehyde), ribose is an
aldopentose (a five carbon
aldehyde), and fructose is a
ketohexose (a six-carbon ketone).
In naming the monosaccharide
name ends with “ose”, example;

Most naturally occurring monosaccharides are pentoses and hexoses.

Carbohydrates that reduce Fehling’s solution (or
Benedict’s) or Tollens’ reagent are known as
reducing sugars. All monosaccharides, whether
aldose or ketose, are reducing sugars. Glucose,
fructose, galactose etc are reducing sugars. Most
disaccharides are reducing sugars; sucrose
(common table sugar) is a notable exception; it is a
non-reducing sugar. All monosaccharide ketoses are reducing sugars because
they tautomerize in solution into aldoses.
Two monosaccharide containing eight and nine
carbon atoms with a ketone carbonyl will
be called what?
Solution:
Eight carbon atom monosaccharide will have a
general name octose with ketone carbonyl it will
become ketooctose.

Nine carbon monosaccharide will have a general

name of ninose with ketone carbonyl it will
become ketoninose.
Hydrolysis of sucrose gives equimolar amounts of D-fructose and
D-glucose.
Physical Properties of Carbohydrates
Carbohydrates exhibit the following physical properties:

Stereoisomerism – Compound sharing the same

structural formula but they differ in spatial configuration.
Example: Glucose has two isomers with respect to the
penultimate carbon atom. They are D-glucose and L-
glucose.
D-glucose (dextrose) is the
enantiomer of the L-glucose. In D-
glucose, three hydroxyl groups and
one hydrogen group attach to the
right side, whereas, in L-glucose,
three hydroxyl groups and one
hydrogen group attach to the left
side. D-glucose can exist in both
linear and cyclic forms, but L-glucose
exists in an equilibrium mixture of α-
L-glucopyranose and β-L-
glucopyranose.
D-glucose is the main
energy source in most living
organisms. L-glucose is a
low-calorie sweetener that
is a good suggestion for
diabetes patients.
Optical Activity – It is the rotation of plane-polarized light
forming (+) glucose and (-) glucose.
Diastereo isomers – It is the configurational change with
regard to C2, C3 or C4 in glucose. Example: Mannose,
galactose.
Anomerism – Two monosaccharides that differ only in the
configuration at the anomeric center are anomers (a special
kind of epimers). Anomers are called alpha (α) or beta (β)
depending on the position of the hydroxyl group.
Consequently, two hemiacetal structures are possible, depending on the
configuration at the hemiacetal carbon, the carbon that forms the new
stereogenic center, is called the anomeric carbon.
For monosaccharides in the D-series, the hydroxyl group is “down” in
the alpha (α) anomer and “up” in the Beta (β) anomer. Example;
Epimerism – Epimers are carbohydrates which
vary in one position for the placement of the -OH
group. Best examples are D-glucose and D-
galactose. Both monosaccharides are D-sugars i.e
the -OH groups on carbon-5 of the hexoses are
located on the right in the Fischer projection.
In summary, the most common hexoses are
glucose, galactose, mannose and fructose. The
first three are aldoses (aldohexoses), whereas
fructose is a ketose (ketohexoses).
Ribose is an aldopentose.
Glucose, galactose and mannose are epimers, in
that they differ from one another at a single
centre of asymmetry.
At a glance;
1. Aldotriose: Glyceraldehyde or glyceral
2. Aldotetrose: Erythrose, threose.
3. Aldopentose: Ribose, arabinose, xylose.
4. Aldohexose: Glucose, mannose, galactose,
gulose, allose and talose.
5. Ketohexose: Fructose, piscose and
sorbose.
Problem: What is the structural relationship
between D-glucose, D-mannose and D-
galactose?
Solution: D-galactose and D-mannose are both
epimers of D-glucose. D-mannose is the C2
epimer of D-glucose, while D-galactose is the C4
epimer of D-glucose.
Self-assessment Exercise
i. What are carbohydrates?
ii What are the importance of Carbohydrates?
iii what are the physical and chemical properties of carbohydrates?
iv. Give four (4) different classes of carbohydrates with at least two
examples each.
v. Differentiate between disaccharides and oligosaccharides.
vi. What are the two important functional groups present in a
carbohydrate?
vii. What are epimers, diastereomers and enantiomers?
viii. Name two epimers of glucose.
ix. Draw the structure of the following and state clearly the
nature of carbonyl carbon present;
(a) aldohexose
(b) ketopentose
(c) aldotriose
(d) ketotetrose
x. Using the Fisher projection formula, write the structural
formula for L-aldotetrose
xi. What is the special name given to diastereomers that
differ in configuration at the one stereogenic center?
Chemical Properties of Carbohydrates
Osazone formation: Osazone are carbohydrate derivatives
when sugars are reacted with an excess of phenylhydrazine. eg.
Glucosazone

Benedict’s test: Reducing sugars when heated in the presence

of an alkali gets converted to powerful reducing species known
as enediols. When Benedict’s reagent solution and reducing
sugars are heated together, the solution changes its colour to
orange-red/ brick red.
Oxidation: Monosaccharides are reducing sugars if their
carbonyl groups oxidize to give carboxylic acids. In Benedict’s
test, D-glucose is oxidized to D-gluconic acid thus, glucose is
considered a reducing sugar.

Reduction to alcohols: The C=O groups in open-chain forms

of carbohydrates can be reduced to alcohols by sodium
borohydride, NaBH4 , or catalytic hydrogenation (H2, Ni,
EtOH/H2O). The products are known as “alditols”.
Monosaccharides : (+)-Glucose: an aldohexose
Glucose is the unit of which starch, cellulose and glycogen are
made up, and because of its special role in processes, is by far
the most abundant, most important monosaccharide. Hence,
most of what needs to be known about monosaccharides can be
learnt from just this one compound.
Carbohydrates, as already defined above, are poly hydroxyl
aldehydes or ketones, thus their properties are those of either of
the two functional groups.
The Fischer projections are used for sugars in their open-
chain form, Haworth projections are often used to depict
sugars in their cyclic forms

The presence of many hydroxyl groups in the molecule

makes it very polar. Therefore, it is soluble in polar
solvents, such as water, sparingly soluble in ethanol and
insoluble in non-polar solvents such as ether and hexane.
Monosaccharides : Galactose
Galactose is found in the disaccharide, lactose
or milk sugar. As a monosaccharide in peas
and avocados. Galactose is classified as a
monosaccharide, an aldose, a hexose and a
reducing sugar.
Monosaccharides : Fructose
Fructose is a ketonic simple sugar, found
naturally in fruits, some vegetables and honey.
It is one of the three dietary monosaccharides,
along with glucose and galactose. It is also a
hexose and a reducing sugar.
CERTAIN CHEMICAL REACTIONS OF
MONOSACCHARIDES
Oxidation of Monosaccharides
Aldoses can be easily oxidized to acids. The
products are called aldonic acids. For
example, D-glucose is easily oxidized to D-
gluconic acid.
Strong oxidizing agents,
such as aqueous nitric acid,
attack the aldehyde group
and the primary
alcohol group to produce
dicarboxylic acids called
aldaric acids. For example,
D-glucose gives D-glucaric
acid.
Reduction
The carbonyl group of aldoses and ketoses can
be reduced by various reagents, the products
are polyols called alditols. For example,
catalytic hydrogenation or reduction with
sodium borohydride (NaBH4) converts D-
glucose to D-glucitol (also called sorbitol).
Sorbitol is useful in pharmaceutical application.
Commonly used in chewable tablets because of
its sweet taste, as plasticizer for gelatin in
capsule formulation, as a laxative to relieve
constipation. Also in cosmetic products like
creams, toothpastes, facemask, hair sprays,
mouthwashes etc as humectants.
What is the difference in
functional group(s) between D-
glucose and D-glucitol
(sorbitol)?
Summary:
In this part, we have learnt that;
i. Carbohydrates are polyhydroxy aldehyde or ketones or compounds that
can be hydrolyzed to them. Chemically, the carbon, hydrogen, and
oxygen bond together in the ratio 1:2:1 (Cx(H2O)y,

ii. Carbohydrates are a major source of metabolic energy eg Glucose. Others

occur as structural material in plants eg cellulose. And as storage in plants
and animals as starch and glycogen.

iii. Carbohydrates can be monosaccharides, disaccharides, oligosaccharides

and polysaccharides. All can be hydrolysed to simpler forms, with the
exception of glucose.
iv. If a monosaccharide contains an aldehyde group, it is
known as an aldose; if it contains a ketone group, it is known
as a ketose. And depending on the number of carbon atoms it
contains, it can be a triose, tetrose, pentose and hexose.

v. All monosaccharides are reducing sugars. Most

disaccharides are reducing sugars except sucrose (common
table sugar).

vi. Carbohydrates exhibit stereoisomerism, optical activity,

epimerism, anomerism etc.
vii. Carbohydrates are expressed in two forms;
open chain and closed-ring form.

viii. Carbohydrates exhibit certain chemical

reactions, characteristics of the functional groups
present. For example, oxidation and reduction.
D-glucose is oxidized to D-gluconic acid. It is
also reduced to sorbitol.
Extended questions
1. Which of the following in an example of an aldopentose?
a) D-Ribose b) Glyceraldehyde c) Fructose d) Erythrose
2. Which of the following in an example of a ketohexose?
a) D-Ribose b) Glyceraldehyde c) Fructose d)
Erythrose
3. Which of the following in an example of an aldotetrose?
b) Glyceraldehyde b) Mannose c) Erythrose d) Ribose
4. Name two aldohexoses and aldopentoses each.
5. Draw the Haworth projection of α-D-Glucose.
6. With chemical equation, show how D-glucose reacts with
concentrated nitric acid. Give the name of the derivative of D-
glucose formed.
7. Show the conversion of D-glucose to D-gluconic acid
8. Show the formation of sorbitol from D-glucose
9. What is the difference between gluconic and glucaric acid?
10. Oxidation of D-glucose with bromine water in the presence of
silver ion gives what product? Show the reaction.
11. Reduction of D-glucose leads to the formation of Sorbitol,
outline the reaction.
TO BE CONTINUED
MODULE 2