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PDF&Rendition 1
PDF&Rendition 1
An asymmetric carbon atom is one that is bonded to four different groups or atoms. This
tetrahedral arrangement around the carbon atom results in a non-superimposable mirror image.
Let's consider a simple example of a molecule with one chiral center, represented by a carbon
atom. If this carbon is bonded to four different substituents or groups, such as A, B, C, and D,
we have two possible configurations: R and S.
The R and S configurations are assigned based on the Cahn-Ingold-Prelog priority rules. These
rules assign priority to the substituents based on the atomic number of the atoms directly
bonded to the chiral carbon. By assigning priorities, we can determine the spatial arrangement
of the molecule and label it as either R (from the Latin "rectus," meaning "right") or S (from the
Latin "sinister," meaning "left").
When we have a molecule with two chiral centers, the complexity increases. Each chiral carbon
can have two possible configurations (R or S), resulting in four possible stereoisomers. These
stereoisomers can be designated as RR, RS, SR, and SS, depending on the configuration of
the two chiral centers.
The study of chirality is crucial in fields like organic chemistry, medicinal chemistry, and drug
development. It is essential to understand the chiral nature of molecules and the potential
differences between their enantiomers to ensure the development of safe and effective drugs.
Geometrical and optical isomerism are two types of stereoisomerism that occur in organic
chemistry. Stereoisomers are molecules that have the same molecular formula and connectivity
of atoms but differ in the arrangement or orientation of atoms in space. Geometrical isomerism
arises due to restricted rotation around a bond, while optical isomerism is related to the
presence of chiral centers in a molecule.
Geometrical Isomerism:
Geometrical isomerism occurs when different groups or atoms are arranged differently around a
rigid bond or a double bond in a molecule. It is also known as cis-trans isomerism or E-Z
isomerism. The two main factors responsible for geometrical isomerism are:
a. Cis-Trans Isomerism: This type of isomerism is observed in molecules that have a rigid
double bond (C=C) or a ring structure. In cis isomers, the substituent groups or atoms are on
the same side of the double bond or ring, while in trans isomers, they are on the opposite sides.
Cis and trans isomers have different physical properties and may exhibit different biological
activities.
b. E-Z Isomerism: This type of isomerism is observed in molecules with restricted rotation
around a bond due to the presence of bulky groups or a double bond. The E (entgegen) isomer
refers to the arrangement of substituents on opposite sides of the double bond, while the Z
(zusammen) isomer refers to the arrangement of substituents on the same side of the double
bond. The E-Z nomenclature is used when the priority of the substituents is determined
according to the Cahn-Ingold-Prelog priority rules.
Optical Isomerism:
Optical isomerism, also known as enantiomerism, occurs when a molecule has one or more
chiral centers. Chiral centers are carbon atoms that are attached to four different substituent
groups. Optical isomers are non-superimposable mirror images of each other and exist in pairs
called enantiomers. These enantiomers have identical physical properties, except for their
interaction with plane-polarized light.
The enantiomers are labeled as R or S based on the Cahn-Ingold-Prelog priority rules, which
assign priorities to the substituents around a chiral center. When a plane-polarized light passes
through a solution of a chiral compound, it can be rotated either clockwise (dextrorotatory,
labeled as +) or counterclockwise (levorotatory, labeled as -), depending on the enantiomer
present. Compounds that rotate plane-polarized light are called optically active, while those that
do not rotate are called optically inactive or racemic mixtures.
It is important to note that while geometrical isomers can have different physical properties,
optical isomers have identical physical properties except for their interaction with
plane-polarized light and their behavior in chiral environments
1. Monosaccharides:
Monosaccharides are the simplest form of carbohydrates and cannot be hydrolyzed into smaller
sugar units. They are classified based on the number of carbon atoms they contain, with the
most common ones being trioses (3 carbons), tetroses (4 carbons), pentoses (5 carbons), and
hexoses (6 carbons). Glucose, fructose, and galactose are examples of monosaccharides. They
are usually colorless, crystalline solids and are sweet-tasting.
2. Disaccharides:
Disaccharides are formed by the condensation reaction (dehydration synthesis) between two
monosaccharide units. This reaction leads to the formation of a glycosidic bond. The most
well-known disaccharides include sucrose (glucose + fructose), lactose (glucose + galactose),
and maltose (glucose + glucose). Disaccharides are soluble in water and have a sweet taste.
3. Polysaccharides:
Polysaccharides are complex carbohydrates composed of many monosaccharide units joined
together by glycosidic bonds. They are generally polymers of glucose and serve as energy
storage molecules or structural components. Some important polysaccharides include:
● Starch: It is the storage form of glucose in plants and consists of amylose (unbranched
chain) and amylopectin (branched chain). Starch is found in grains, potatoes, and other
plant-based foods.
● Cellulose: It is the most abundant polysaccharide on Earth and forms the structural
component of plant cell walls. Unlike starch, cellulose is indigestible by most organisms
due to the different glycosidic bond orientation.
● Solubility: Monosaccharides and small disaccharides are generally soluble in water due
to their hydrophilic nature. However, as the size of the carbohydrate molecule increases,
solubility decreases.
● Structural roles: Polysaccharides like cellulose and chitin provide structural support to
plants and animals, respectively.
Carbohydrates have diverse functions and are essential for the proper functioning of biological
systems.
Glucose and fructose are monosaccharides that exist in both open-chain and cyclic forms. They
undergo a process called intramolecular cyclization, where the carbonyl group (either an
aldehyde in glucose or a ketone in fructose) reacts with a hydroxyl group in the same molecule,
forming a cyclic structure.
1. Glucose:
a. Open-chain structure: In the open-chain form of glucose, also known as the straight-chain or
acyclic form, it exists as an aldehyde. Glucose has six carbon atoms, and the carbon atom
containing the aldehyde group is known as the anomeric carbon. The open-chain structure of
glucose can be represented as:
H-(CHO)-(CHOH)-(CHOH)-(CHOH)-(CHOH)-(CH₂OH)
α-glucose:
HO-CH₂-(CHOH)-(CHOH)-(CHOH)-(CHOH)-H
β-glucose:
H-(CHOH)-(CHOH)-(CHOH)-(CHOH)-CHO
2. Fructose:
a. Open-chain structure: In the open-chain form of fructose, it exists as a ketone. Fructose has
six carbon atoms and a ketone group on the second carbon atom. The open-chain structure of
fructose can be represented as:
H-(CHOH)-(C=O)-(CHOH)-(CHOH)-(CHOH)-H
b. Cyclic structure: Fructose also undergoes intramolecular cyclization to form a cyclic structure.
The ketone group reacts with the hydroxyl group on the fifth carbon atom, resulting in the
formation of a hemiketal. Fructose forms a five-membered ring called a furanose ring. Similar to
glucose, fructose also exists as α-fructose and β-fructose, depending on the configuration of the
hydroxyl group attached to the anomeric carbon.
α-fructose:
HO-(CHOH)-(C=O)-(CHOH)-(CHOH)-H
β-fructose:
H-(CHOH)-(C=O)-(CHOH)-(CHOH)-OH
The cyclic forms of glucose and fructose are the predominant structures found in aqueous
solutions, as they are more stable compared to the open-chain forms. These cyclic structures
are important in carbohydrate chemistry and have implications for the biological functions and
properties of glucose and fructose