Smoc2223006 Paper 2 (Sankalp)

DEPARTMENT OF
CHEMISTRY
Topic: Radicals in Synthesis
Name: Sankalp Sagar Katale

Msc Part 2
Roll no: SMOC2223006
Sr.no. Content
1 Introduction
2 Inter and intra molecular C-C bond formation via,
tin hydride, mercuric hydride,thiol donar.
3 Cleavage of C-X, C-Sn, C-Co, C-S, O-O bonds.

4 Oxidative coupling, C-C bond formation in aromatics:
SNAr
5 Name reactions: Hunsdiecker reaction, Sandmeyer

reaction.
6 Research paper
7 Bibliography
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Inter and Intra molecular C-C bond
formation via
Tin hydride:-
AIBN =
TBTH =

formation via
Reaction:

Baldwin’s Rule
Nomenclature:
Tetrahedral (sp3) - tet

Trigonal (sp2) - trig
Diagonal (sp) - dig
Exo 5-exo-trig
5-exo-trig > 6-endo-trig
(7-endo-trig, 8-endo-trig) > 5-exo-trig
Endo 6-endo-trig

formation via
Reaction:
Mechanism:

formation via
Mercuric hydride:-
Alkyl mercury halides reduces to alkyl mecury hydrides which is to unstable
at r.t. due to very weak Hg-H bond.

formation via
Reaction:
Mechanism:

formation via
: :

formation via
Thiol donar:-
:
Cleavage of C-X
The bond dissociation energies of carbons – halogen bond increases in
the order C-I < C-Br < C-Cl < C-F.
In the following reaction involves cleavage of C-X bond.

Cleavage of C-Sn
Reaction:
Mechanism:

Cleavage of C-Co
Reaction:

Cleavage of C-S
Reaction:

Cleavage of O-O
Peroxides, a radical initiators which on thermolysis or photolysis
undergo cleavage of O-O single bond generates peroxide radical.
Oxidation of organic molecule in presence of molecular oxygen leads

to the formation of hydro peroxides, this is know as autoxidation.

Cleavage of O-O
Reaction:

Oxidative Coupling
 It is a coupling reaction in which two molecular entites are coupled through
oxidation process. Many of this reaction involves C-C formation.

Aromatic Nucleophilic Subtsitution
Through Radical Intermediate (SNAr)
• A certain substituent in an aromatic compound is replaced by a
nucleophile through an free radical intermediate species.
Deactivating group on aromatic ring favours the regular nucleophilic

substitution reaction (ionic).It is not required.

Aromatic Nucleophilic Subtsitution
Through Radical Intermediate (SNAr)
Mechanism:- Examples:-

C-C Bond Formation In Aromatics

Name reaction: Hunsdiecker reaction
General Reaction:-
Examples:-

Name reaction: Sandmeyer reaction

Name reaction: Sandmeyer reaction
Examples:

Research paper
Abstract:-Free radicals and other oxidants have gained importance in the field of biology due to their central role in various
physiological conditions as well as their implication in a diverse range of diseases. The free radicals, both the reactive oxygen
species (ROS) and reactive nitrogen species (RNS), are derived from both endogenous sources (mitochondria, peroxisomes,
endoplasmic reticulum, phagocytic cells etc.) and exogenous sources (pollution, alcohol, tobacco smoke, heavy metals, transition
metals, industrial solvents, pesticides, certain drugs like halothane, paracetamol, and radiation). Free radicals can adversely affect
various important classes of biological molecules such as nucleic acids, lipids, and proteins, thereby altering the normal redox
status leading to increased oxidative stress. The free radicals induced oxidative stress has been reported to be involved in several
diseased conditions such as diabetes mellitus, neurodegenerative disorders (Parkinson’s disease-PD, Alzheimer’s disease-AD and
Multiple sclerosis-MS), cardiovascular diseases (atherosclerosis and hypertension), respiratory diseases (asthma), cataract
development, rheumatoid arthritis and in various cancers (colorectal, prostate, breast, lung, bladder cancers). This review deals
with chemistry, formation and sources, and molecular targets of free radicals and it provides a brief overview on the pathogenesis
of various diseased conditions caused by ROS/RNS.
Bibliography
Organic Chemistry, Clayden Greeves Warren and Wothers Oxford
Press (2001), Chp-39, Pg. No.- 1040-1050.
Advanced Organic Chemistry Part B: Reaction and Synthesis Fifth
Edition, Francis A. Carey and Richard J. Sunberg, Chp-10- (956-989).
Modern Methods Of Organic Synthesis, Willam Carruthers and Iain
Coldham, Fourth Edition, Cambridge (268-279).
https://www.researchgate.net/publication/272015922_Free_Radicals_
Properties_Sources_Targets_and_Their_Implication_in_Various
_Diseases

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DEPARTMENT OF

Topic: Radicals in Synthesis

Name: Sankalp Sagar Katale

3 Cleavage of C-X, C-Sn, C-Co, C-S, O-O bonds.

5 Name reactions: Hunsdiecker reaction, Sandmeyer

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Tetrahedral (sp3) - tet

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Oxidation of organic molecule in presence of molecular oxygen leads

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Deactivating group on aromatic ring favours the regular nucleophilic

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