Que. 1 .

Discuss various types of structural isomerism in

organic compound with relevant examples ?
There are two primary types of isomerism, Structural Isomerism and Stereoisomerism.

Chain Isomerism
• It is also known as skeletal isomerism.
• The components of these isomers display differently branched structures.
• Commonly, chain isomers differ in the branching of carbon
• An example of chain isomerism can be observed in the compound C5H12, as illustrated
below.

Position Isomerism
• The positions of the functional groups or substituent atoms are different in position
isomers.
• Typically, this isomerism involves the attachment of the functional groups to different
carbon atoms in the carbon chain.
• An example of this type of isomerism can be observed in the compounds having the
formula C3H7Cl.

Functional Isomerism
• It is also known as functional group isomerism.
 • As the name suggests, it refers to the compounds that have the same chemical formula
but different functional groups attached to them.
• An example of functional isomerism can be observed in the compound C3H6O.

Metamerism
• This type of isomerism arises due to the presence of different alkyl chains on each side of
the functional group.
• It is a rare type of isomerism and is generally limited to molecules that contain a divalent
atom (such as sulphur or oxygen), surrounded by alkyl groups.
• Example: C4H10O can be represented as ethoxyethane (C2H5OC2H5) and methoxy-propane
(CH3OC3H7).

Tautomerism
• A tautomer of a compound refers to the isomer of the compound which only differs in the
position of protons and electrons.
• Typically, the tautomers of a compound exist together in equilibrium and easily
interchange.
• It occurs via an intramolecular proton transfer.
• An important example of this phenomenon is Keto-enol tautomerism.

Ring-Chain Isomerism
• In ring-chain isomerism, one of the isomers has an open-chain structure whereas the other
has a ring structure.
• They generally contain a different number of pi bonds.
• A great example of this type of isomerism can be observed in C3H6. Propene and
cyclopropane are the resulting isomers, as illustrated below.
Que. 2. Draw the potential energy diagram of butane
and discuss it in brief ?
Conformers of Butane
Butane is an alkane with the presence of C-C bonds. Normally, when we rotate the molecule of
butane at the axis of the C-C bond, it shows different conformation isomerism. Generally, Butane
has four conformation isomers which are fully eclipsed, gauche, eclipsed, and anti butane
conformational isomers. Lets us discuss these isomers below.

▪ When we look at the chemical structure of butane, we can see

that it has two substituents which are methyl groups attached to
the two end carbon atoms. The methyl group is comparatively
larger than hydrogen atoms. However, we can also see that
everything on the front side is eclipsing with the structure in the
backside. One methyl group is present in front of the other methyl
group, and the other hydrogen atoms are kept at the back of other
hydrogen atoms. In short, the structure is completely eclipsing or
they are fully eclipsed.
▪ Now, if we rotate the front methyl group by 60° or when the
dihedral angle is 60° then there is a formation of gauche or
staggered conformation. It basically has the presence of identical
groups at 60 degrees from one another. This type of conformation
is more stable as there is a little steric hindrance between the
same molecules.
▪ If we make the dihedral angle as 120° then this form of isomer is
also known as eclipsed conformation. However, this eclipsed
form is quite different from the previous fully eclipsed state. The
basic difference is that in this the methyl group is eclipsing the
hydrogen atom and not the methyl group.
▪ On rotating the isomer at an angle of 180° the two methyl groups
are found to lie exactly opposite to each other. This conformation
is known as staggered conformation or anti conformation.
Usually, each conformer is also interconverted to the same forms by rotating the isomer around
the central carbon single bond. Eclipsed conformer can be converted back into gauche
conformation by rotating it 60 degrees and when an eclipsed is rotated by 180 degrees it forms
anti- conformer. Rotation of anti butane by 120 degrees again leads to the formation of the
gauche conformed.

Ranking of Conformation Isomers

The ranking of the conformational isomers is given below taking into account the energy levels
from lowest to highest. It is given as;
•
o
▪
1. anti
2. gauche
3. eclipsed
4. fully eclipsed
Que. 3. Discuss the synthetic scheme of paracetamol
and discuss it’s use ?
Paracetamol (acetaminophen; N-acetyl-p-aminophenol; APAP) is an analgesic and fever-reducing
medicine:

It is an active ingredient in many widely sold over-the-counter medicines, such as Tylenol and
Panadol. As a prescription pharmaceutical it is also sold in combination with opioid pain medications
for treating more severe pain. It is the most commonly used medication for pain and fever in the
United States. It is on the World Health Organizations List of Essential Medicines.
Introduced in the early 1900s, acetaminophen is a coal tar derivative that acts by interfering with the
synthesis of prostaglandins and other substances necessary for the transmission of pain impulses.
Although its action is similar to that of aspirin, it lacks aspirin's anti-inflammatory and blood-thinning
effects, is less irritating to the stomach, and can be used by people who are allergic to aspirin. Heavy
use has been linked to an increased incidence of liver failure, especially in alcoholic patients.
The original synthesis starts with phenol, which is nitrated with sodium nitrate to yield a mixture of
ortho- and para-nitrophenol. These are then separated by distillation. The nitro group of the para-
nitrophenol is then reduced to an amine, giving para-aminophenol. The amine is then acetylated with
acetic anhydride:
Ques 4: Describe the SN1 mechanism of
substitution reaction?

Step 1

• The carbon-bromine bond is a polar covalent bond.

The cleavage of this bond allows the removal of the
leaving group (bromide ion).
• When the bromide ion leaves the tertiary butyl
bromide, a carbocation intermediate is formed.
• As mentioned earlier, this is the rate-determining
step of the SN1 mechanism.
• It is important to note that the breaking of the
carbon-bromine bond is endothermic.

Step 2

• In the second step of the SN1 reaction mechanism,

the carbocation is attacked by the nucleophile.
• Since water is used as a solvent, an oxonium ion
intermediate is formed.
 • Since the solvent is of a neutral nature, a third step
where deprotonation occurs is necessary.

Step 3

• The positive charge on the carbocation was shifted

to the oxygen in the previous step.
• The water solvent now acts as a base and
deprotonates the oxonium ion to yield the required
alcohol along with a hydronium ion as the product.
• Step 2 and Step 3 of this reaction are fast.
Ques 5: Discuss various ring-opening reactions of
cyclopropane.