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Chemistry-Theory (Cyi 101) Organic Chemistry

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CHEMISTRY-THEORY(CYI 101)

Organic Chemistry
Parthasarathi Das
Department of Chemistry
Indian Institute of Technology (ISM) Dhanbad
Dhanbad-826004
Email: partha@iitism.ac.in
9419227993

7th Dec 2020/Sec G/H


CYI 101 CHEMISTRY-THEORY (Common) (3-0-0)

UNIT –II

Aromaticity [2L]
Aromatic, non-aromatic and anti-aromatic compounds

Stereochemistry [4L]
Concept of chirality, Axial chirality, enantiomers and diastereomers, specific rotation,
optical purity, Racemic modification and resolution, R/S, D/L and E/Z nomenclature

Pericyclic reactions [4L]


Definitions, Classifications, photochemical [2+2] and thermal [4+2] cycloaddition,
Sigmatropic rearrangement

Macromolecules [4L]
Introduction to peptides and proteins. Basics of Polymer Chemistry, Polymerization
techniques, natural and synthetic polymer
Recommended Books:
1. Organic Chemistry, J. Clayden, N. Greeves, S. Warren, P. Wother, Oxford University
Press, 2000.
2. Principles of polymerization, George G. Odian, 4th Edn, John Wiley & Sons, Inc.,
Publication, 2004.
3. Lehninger Principles of Biochemistry 6th Edition by David L. Nelson; Michael M.
Cox, Macmillan International Higher Education
COVID-19 Management

Hydroxy
chloroquine Favipiravir

Dexamethasone

Remdesivir
Paracetamol
Aspirin

Dichlorodiphenyltrichloroethane (DDT)/
Insecticide Azo dye
Kekulé’s First Structure of Benzene

1865 - Proposes a cyclic structure


for benzene with alternating single
and double bonds

1890- Benzene Fest - Kekulé’s Dream


August Kekulé
(1829-1896)
Aromaticity
Aromatic/Heteroaromatic
Aromaticity
• The molecule must be Cyclic
• Every atom in the ring must be conjugated
• The molecule must be Flat
• The molecule must contain 4n+2 p electron

Hückel's Rule
Among planar, cyclic, completely conjugated polyenes, only those with 4n + 2
p electrons possess special stability are aromatic

So for n = 0 , we have [4 (0) + 2] = 2


for n = 1 , we have [4 (1) + 2 ] = 6
for n = 2, we have [4 (2) + 2 ] = 10
for n = 3, we have [4 (3) +2 ] = 14
for n=4, we have [4 (4) +2 ] = 18
Aromaticity

• Where [4n + 2] is a formula describing the number series: 2, 6, 10, 14, 18, 22, 26….
• These are “magic numbers” for aromaticity; the number of pi electrons in the molecule in order for the
molecule to be aromatic
(We often call number must be in this series in this series, “Huckel numbers”)
Heterocyclic
Anti-Aromaticity
Cyclopentadiene Vs Cyclopentadienyl anion

Base

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