Module – 3 (part – 2)

Introduction to reactions involving

Addition

Elimination
Organic Reaction Oxidation
Reduction

Cyclization
Ring Openings
Substitution Reactions
In a substitution
reaction, generally, one
atom or a group of
atoms take place of
another atom or a
group of atoms which
leads to the formation of
an altogether new
substance.
SN2 Mechanism
SN2 reactions are bimolecular in rate of reaction and have
a concerted mechanism.
The process involves simultaneous bond formation by the
nucleophile and bond cleavage by the leaving group.
For reactivity using an SN2 mechanism, primary >>
secondary >> tertiary carbon centers.
SN1 Mechanism
 Unimolecular in rate of reaction
 Two steps
 First step – Bond Cleavege by Leaving group (LG)
 Generate a carbocation intermediate.
 Second step, the electronegative nucleophile attacks the carbocation
to form the product.
 The nucleophile can attach either side of the carbocation, which
adopts an sp2-hybridized orbital with a trigonal planar geometry,
 For reactivity using an SN1 mechanism, tertiary >> secondary >>>
primary carbon centers.
Addition Reaction
The most common chemical transformation of a carbon-carbon
double bond is the addition reaction.
Oxidation and reduction Reaction
Oxidation - Addition of Oxygen or removal of hydrogen
Reduction – Removal of Oxygen of addition of Hydrogen
 Heteroatoms such as oxygen and nitrogen
are more electronegative than carbon, so when a
carbon atom gains a bond to a heteroatom, it
loses electron density and is thus being
oxidized.
Conversely, hydrogen is less electronegative
than carbon, so when a carbon gains a bond to a
hydrogen, it is gaining electron density, and
thus being reduced.
 Two important reagents for the reduction of aldehydes and
ketones to alcohols are sodium borohydride (NaBH4) and lithium
aluminum hydride (LiAlH4)
Elimination Reactions
There are certain reactions which involve the elimination
and removal of the adjacent atoms. After these multiple
bonds are simultaneously formed and there is a release of small
molecules as products as a result.
One of the examples of a typical elimination reaction is the
conversion of ethyl chloride to ethylene.
CH3CH2Cl → CH2= CH2 + HCl
In the above reaction, the eliminated molecule is HCl, which can
form out of the combination of H+ from the carbon atom which
is on the left side and Cl– from the carbon atom which is on the
right side.
[Link]
E1 type
 two-step removal mechanism process
 also known as unimolecular elimination
 formation of an intermediate
 the reaction rate is proportional to the concentration of the
compound to be transformed – first-order kinetics
 regioselective and follows Zaitsev’s rule, i.e., favors the
formation of Zaitsev product
E2 type
 one step removal mechanism process
 also known as bimolecular reaction
 carbon-leaving group and carbon-hydrogen bonds break off
simultaneously
 the reaction rate is proportional to both the compound to be
transformed and the transferring agent – second-order kinetics
 stereoselective and regioselective
Ring-Opening
Epoxides are three-membered rings containing an oxygen atom. They are
associated with high ring tension and this is the basis of their reactivity
towards nucleophiles despite lacking a good leaving group
Epoxide Ring-Opening by Other Nucleophiles
cyclization reaction
The Nazarov cyclization reaction (often referred to as simply
the Nazarov cyclization) is a chemical reaction used in organic
chemistry for the synthesis of cyclopentenones.
Cyclization reaction (Dieckmann condensation)
The Dieckmann condensation is the intramolecular chemical
reaction of diesters with base to give β-ketoesters.
It is named after the German chemist Walter Dieckmann
(1869–1925).

cyclic β-keto esters,

Ref.:
[Link]
nic_Chemistry)/Reactions/Organic_Reactions/Dieckmann_Condensation
Paracetamol (Acetaminophen)

para-acetaminophenol

Paracetamol (Panadol, Calpol, Alvedon) is an analgesic and antipyretic drug that is used to
temporarily relieve mild-to-moderate pain and fever. It is commonly included as an
ingredient in cold and flu medications and is also used on its own
Paracetamol is available over-the-counter (OTC) and also as a prescription
medication. It is used for the relief of:
 Headache
 Tension headache
 Migraine
 Backache
 Rheumatic and muscle pain
 Mild arthritis/osteoarthritis
 Toothache
 Period pain (dysmenorrhea)
 Colds and flu symptoms
 Sore throat
 Sinus pain
 Post-operative pain
 Fever (pyrexia)
Aspirin is prepared by chemical synthesis from salicylic
acid, through acetylation with acetic anhydride.
Aspirin is an oral non-steroidal anti-inflammatory drug
(NSAID) that is rapidly absorbed from the stomach and
the small intestine.

Aspirin is used to reduce fever and relieve mild to moderate pain from conditions such as
muscle aches, toothaches, common cold, and headaches.
Ibuprofen
Ibuprofen is used to relieve pain from various conditions such as headache, dental
pain, menstrual cramps, muscle aches, or arthritis. It is also used to reduce fever and to
relieve minor aches and pain due to the common cold or flu. Ibuprofen is a nonsteroidal anti-
inflammatory drug (NSAID)

2-(4-Isobutylphenyl)propanoic acid
 Amoxicillin
Amoxil (amoxicillin) is a penicillin-type antibiotic used to treat infections
caused by bacteria that are b-lactamase negative (b-lactamase positive bacteria are
usually resistant to amoxil); these infections usually occur in the skin, lungs, urinary
tract and eye, ears, nose, and throat.

(2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-
azabicyclo[3.2.0]heptane-2-carboxylic acid