Organic chemistry textbook

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Pharmacy Exam

Guide

Step I

PHARMACEUTICAL

CHEMISTRY-I 

(ORGANIC-I)  

st
1  Edition

(p1c2)

Conjugation 1
 

Chapter 1 Conjugation …………………………………………………………………………………………………………………….. 3

Chapter 2 Hyper Conjugation ……………………………………………………………………………………………………………. 5

Chapter 3 Steric Effect …………………………………………………………………………………………………………………….. 6

Chapter 4 Inductive Effect ………………………………………………………………………………………………………………… 7

Chapter 5 Mesomeric Effect ……………………………………………………………………………………………………………… 8

Chapter 6 Hydrogen Bonding ……………………………………………………………………………………………………………. 9

Chapter 7 Theory of Resonance ………………………………………………………………………………………………………. 11

Chapter 8 Keto-Enol Tautomerism …………………………………………………………………………………………………… 12

Chapter 9 SN Reaction ……………………………………………………………………………………………………………………. 13

Chapter 10 Electrophilic Substitution Reaction ……………………………………………………………………………………. 14

Chapter 11 Baeyer Villiger ………………………………………………………………………………………………………………… 16

Chapter 12 Diel- Alder Reaction ………………………………………………………………………………………………………… 17

Chapter 13 Fredel Craft Reaction ………………………………………………………………………………………………………. 18

Chapter 14 Metal Hydride Reduction …………………………………………………………………………………………………. 19

Chapter 15 Wolf Kishner Reduction …………………………………………………………………………………………………… 20

Chapter 16 Perkin Condensation ……………………………………………………………………………………………………….. 21

Chapter 17 Cannizaro Reaction …………………………………………………………………………………………………………. 22

Chapter 18 Organometallic Compound ………………………………………………………………………………………………. 23

Chapter 19 Carbonium Ions ………………………………………………………………………………………………………………. 24

Chapter 20 Pinacol- Pinacolone Rearrangement ………………………………………………………………………………….. 25

Chapter 21 Wager-Merwein Rearrangement ………………………………………………………………………………………. 26

Chapter 22 Hoffman’s Rearrangement ………………………………………………………………………………………………. 27

Chapter 23 Beckmann Rearrangement ………………………………………………………………………………………………. 28

Chapter 24 Aldol Condensation …………………………………………………………………………………………………………. 30

Chapter 25 Favorskii Rearrangement …………………………………………………………………………………………………. 31

Chapter 26 Witting Reaction …………………………………………………………………………………………………………….. 32

Chapter 27 Stereochemistry ……………………………………………………………………………………………………………… 33

Chapter 28 Free Radical ……………………………………………………………………………………………………………………. 42

Chapter 29 Alcohol, Phenol and Ethers ………………………………………………………………………………………………. 44

Chapter 30 Alcohol ………………………………………………………………………………………………………………………….. 44

Chapter 31 Phenol …………………………………………………………………………………………………………………………… 46

Chapter 32 Ethers ……………………………………………………………………………………………………………………………. 47

Chapter 33 Aldehyde and Ketones …………………………………………………………………………………………………….. 48

Chapter 34 Carboxylic Acid ……………………………………………………………………………………………………………….. 49

Chapter 35 Amide and Amine …………………………………………………………………………………………………………… 50

Chapter 36 Lactones ………………………………………………………………………………………………………………………… 51

Chapter 37 Lactam ………………………………………………………………………………………………………………………….. 52
 

Chapter 38 Diazonium Ion & Diazonium Salt ………………………………………………………………………………………. 53

Chapter 39 Heterocyclic Compounds …………………………………………………………………………………………………. 55

Chapter 40 Azole …………………………………………………………………………………………………………………………….. 58

Pharmacy Exam Guide 
 

Conjugation 2
 

 

Chapter 41 Furan (Oxole) …………………………………………………………………………………………………………………. 60

Chapter 42 Indole ……………………………………………………………………………………………………………………………. 62

Chapter 43 Pyridine (Azine) ……………………………………………………………………………………………………………… 63

Chapter 44 Quinoline ………………………………………………………………………………………………………………………. 65

Chapter 45 Thiole ……………………………………………………………………………………………………………………………. 67

 
 

 

Pharmacy Exam Guide 
 

Conjugation 3
 

 

Chapter 1 Conjugation
 
 Electron density shifts from one place to

another
 

 
 Delocalization of electron is the shifting of 

electron density. It is done to make a  Each carbon atom have p-orbitals, electrons
molecule more stable. are in motion. They make bonds by jumping.
 Thus electron density may increase or

Shelf Life: Shelf Life is the time interval between date decrease around the three carbon atoms. So
of manufacturing of a drug and the date of expiry of molecule may become like    – CH2 – CH = CH2  

2
that drug.  Similarly, in benzene, each carbon atom is sp  
It is increased to keep the medicine available for use hybridized and it’s structure is planar (one at
for a longer period of time. specific angle)
 

 Molecules possessing CH2= CH2 (multiple Each carbon atom in Benzene is “planar”
bond/degree of unsaturation), conjugation 
occurs.  If angles are not specific then electron density
CH2= CH2 (have got one sigma and one pi- cannot shift. Each carbon atom forms 3 sigma

2
bond) → sp hybridization. bonds, 2 with adjacent carbons and one with

 This electron density cannot shift because hydrogen and it also possess one
electronegativity difference between both the unhybridized p-orbital. Since all six carbon
carbons is same.  atoms possess six unhybridized p-orbitals, two

 Pi bonds are formed because half electron forms are possible.
density is above and half is below.  

 If electron density shifts then it is called
“delocalized” and if it cannot shift then it is
called as “localized”

DEFINITION
 The process of electron density shifting from

one place to another is known as conjugation
in which electron density decreases at one
place and increases correspondingly at some
other place.

 
1.1 EXPLANATION 

 In case of sigma bond, the electron pair is CONDITIONS FOR CONJUGATION
shared between the two nuclei while in pi-

1) There must be p-orbitals on 3 adjacent atoms
bond the electron density exists above and

2) The atoms having p-orbitals must be in same plane
below the bond axis. If it is not able to shift it
is called “localized” e.g. Ethene (CH 

2 = CH2).
While in compounds having more than 3-p CHARACTERISTICS
orbitals on adjacent atoms, may cause  The conjugated ion, radical and molecule are
electron shifting as in allyl radical or benzene. more stable than non-conjugated system.

  The difference in energy between conjugated
Radical: Radical is a specie available for molecule and theoretical unconjugated
attachment or reaction 

molecule (analogue) is called “delocalized or
CH2 = CH-   (Vinyl radical) resonance energy”
CH2 = CH2-CH2-  (Allyl radical)  The molecule in which conjugated orbital is

linear are said to be “linear conjugated”

Pharmacy Exam Guide 
 

Conjugation 4
 

 

molecule while in which it’s branched is called
“cross conjugated”