Definition of Organic Chemistry (Historical Background) (1); l.

2 Justification of Separate Study of

Organic Compounds (l); 1.3 Sources of Organic Compounds (2); 1.4 Importance of Organic
Compounds (2); 1.5 Bonding in Organic Compounds (2); 1.6 Representation of Organic Molecules (6);
1.7 Polar and Non-Polar Bonds (7); l.8 Hydrogen Bonding in Organic Compounds (9); 1.9
Intermolecular Forces (12); Ll 0 Resonance (12); 1.11 Purification of Organic Compounds (15); 1.12
Criteria of Purity of Organic Compounds (17); Summary (18); Questions (20); Answers (23);
ObjeGtive Questions (25); Assertion-Reason Type Questions (31); Answers Objective Questions (32);
Brain Storming Problems (33); Linked Comprehension Type Questions (36).

Pages

1-38

Molecular Analysis of Organic Compounds 39-65 ;. .,," .. ~ . 2.1 General (39); 2.2 Detection of
Elements (Qualitative Analysis) (39); 2.3 Estimation of Elements (Quantitative Analysis) (42); 2.4
Determination of Molecular Mass (47); 2.5 Empirical Formula and Molecular Formula (51); 2.6
Molecular Formula of G!1seous Hydrocarbons (52); 2.7 Modem Methods of Structure Elucidation
(54); Summary (55); Questions (56); Answers (57); Numerical Problems for Practice (58); Objective
Questi9ns (59); AssertionReason Type Questions (62); Answers Objective Questions (63); Brain
Storming Problems (64); Linked Comprehension Type Questions (65). Q

Classific'iltionand N'omenclature of OrganiC Compounds - 66-116

3.1 Classification of Organic Compounds (66); 3.2 Saturated and Unsaturated Compounds (69); 3.3
Nomenclature of Organic Compounds (69); Trivial System (69); IUPAC System (74); IUPAC
Nomenclature of Organic Compounds in Bond'Line Structures (78); 3.4 IUPAC System of
Nomenclature of Complex Compounds (80); 3.5 IUPAC Nomenclature of Alicyclic Compounds (88);
3.6 Writing the Structural Formula from the given IUPAC Name (91); Summary (94); Questions (95);
Answers (99); Objective Questions (101); Assertion-Reason Type Questions (107); Answers Objective
Questions (108); Brain Storming Problems (109); Linked Comprehension Type Questions (1 i 4).

Isomerism 117-180

4.1 Introduction (117); 4.2 Chain or Nuclear Isomerism (118); 4.3 Position Isomerism (119); 4.4 Ring-
Chain Isomerism (119); 4.5 Functional Isomerism (120); 4.6 Metamerism (120); 4.7 Tautomerism
(121); 4.8 Geometrical Isomerism (125); 4.9 Optical Activity (131); 4.10 Optical Isomerism of Lactic
Acid (134); 4.11 Optical Isomerism in Tartanc Acid (134); 4.12 Number of Possible Stereoisomers in
Compounds Containing Different Number of Asymmetric Atoms (135); 4.13 Resolution of Racemic
Mixtures (137); 4.14 Diastereomers (139); 4.15 Fischer Projec'tion Formulae (139); 4.16 Specification
of Configuration (140); 4.17 Conformational Isomerism (147); Summary, (150); Questions (152);
Answers (156); Objective Q!lestions (160); Assertion-Reason Type Questions (168); Answers
Objective Questions (169); Brain Storming Problems (170); Linked Comprehension Type Questions
(178).

Mechanism of Orgahic Reactions 181-258

5.1 Introduction(181); 5.2 Electronic Displacement in Covalent Bonds (l81); Inductive Effect (l81);
Electromeric Effect (185); Resonance and Mesomeric Effect (185); Hyperconjugation (187); 5.3
Fission or Cleavage or Breaking of a Covalent Bond (190); 5.4 Reaction Intennediates (190); Free
RadIcals (190); Carbocations (192); Carbanions (193); Carbenes (194); Carbylamine Reaction (196);
Reimer-Tiemann Reaction (196); 5.5 Nature of Attacking
(x)

Reagents (199); 5.6 Types of Organic Reactions (200); 5.7 Types of Mechanism (202); 5.8 Mechanism
of Substitution Reactions (203); Free Radical Substitution Reactions (203); Nucleophilic Substitution
(206); Electrophilic Substitution (210); 5.9 Mechanism of Addition Reactions (210); Electrophilic
Addition Reactions (210); Addition Reactions in Alkadienes (213); Nucleophilic Addition Reactions
(215); Free Radical Addition Reactions (216); 5.10 Mechanism of Elimination Reactions (216);
Summary (224); Questions (230); Answers (233); Objectb:.e Questions (236); Asseltion-Reason Type
Questions (248);Answers Objective Questions (249); Brain Storming Problems (250); Linked
Comprehension Type Questions (255).

6.1 Hydrocarbons (259); 6.2 Saturated Hydrocarbons (259); 6.3 Structural Isomerism in Alkanes
(260); 6.4 Natural Sources (occurrence) of Alkanes (260); 6.5 General Methods of Preparation (260);
6.6 General Characteristics of Alkanes (265); 6.7 Petroleum (272); LPG and CNG (Petroleum Gases)
(274); 6.8 Artificial Methods for Manufacture of Petrol or Gasoline (274); 6.9 Knocking and Octane
Number (275); 6.10 CetaneNumber (276); 6.11 Flash Point (277); 6.12 Petrochemicals (277);
Summary (277); Questions (280); Answers (282); Problems Based on Properties and Structure (284);
Objective Questions (287); Assertion~Reason Type Questions (293); Answers Objective Questions
(293); Brain Stonning Pr.oblems (294); Linked Comprehension Type Questions (296).

7.1 Introduction (298); 7.2 Nomenclature of Alkenes (298); 7 j Isomerism inAlkenes (299); 7.4
Stability' of Alkenes (299); 7.5 General Methods of Preparat~on of Alkenes (300); 7.6 General
Characteristics of Alkenes(306); 7.7 Alkynes (323); 7.8 Isomerism inAlkynes (324); 7:9 General
Methods of Preparation ofAlkynes (324); 7. 10 General Characteristics ofAlkynes (325); 7.11 Tests of
Un saturation (333); Degree of Un saturation (334); 7.12 Inter, conversions (335); 7.13 Separation of
Alkane, Alkene and Alkyne (336); 7.14 Distinction Between Alkanes, Alkenes .~ -and Alk:ynes(337);
7.15 Cycloalkanes (342); 7.16 Baeyer's Strain Theory (343); 7.17 Cycloalkenes(344)~7.18 Dienes
(34,4); Summary (350); Questions (356);Answers (361); Problems Based on Structure and Properties
(363); Objective Questions (365); Assertion-Reason Type Questions (375); Answers Objective
Questions (376); Brain Storming Problems (377); Linked Comprehension Type Questions (386).

8.1 Halogen Derivatives of Alkanes (388); 8.2 Isomerism in Monohalogen Derivatives.(390); 8.3
General Methods of. Preparation of Monohalogen Derivatives (392); 8.4 Properties of Alkyl Halides
(395); 8.5 Di-halogen Derivatives (401); 8.6 Tri-halogen Derivatives, Chloroform (402);8.7 Iodoform
(405); 8.8 Carbon Tetrachloride (406); 8.9 Unsaturated Halides (407); 8.10 Some More Important
Halogen Derivatives (408); 8.11 Organometallic Compounds (411); Summary (413); Questions (418);
Answers (423); Problems Based on Structure and Properties (425); Objective Questions (428);
Assertion-Reason Type Questions (438); Answers Objective Questions (439); Brain Storming
Problems (440); Linked Comprehension Type Questions (445). '

4484682;",

9.1 Introduction (449); 9.2 Monohydric Alcohols (449); 9.3 Nomenclature (450); 9.4 Isomerism (451);
9.5 General Methods of Preparation of Monohydric Alcohols (453); 9.6 General Characteristics of
Alcohols (460);9.7 Methods of Distinguishing Between Primary, Secondary and Tertiary Alcohols
(469); 9.8 Analytical Tests for Alcohols (470); 9.9 Some Commercially Important Alcohols, Methyl
Alcohol (470); Ethyl Alcohol (471); 9.10 Alcoholic Beverages andAlcoholometry,(473); 9.11
Interconversions (474); Conversion of Ethyl Alcohol into Various Compounds (476); 9.12 Ethylene
Glycol (477); 9.13 Glycerol ( 479); 9.14 Estimation of the number of Hydroxyl Groups in a Polyhydric
Alcohoh(4-84);9.15 Unsaturated Alcohols (484); Summary (491); Questions (495); Answers (502);
Problems Based .on Structure and Properties (505); Objective Questions (506); Assertion-Reason
Type Questions (517); Answers Objective.Questions (518); Brain Stonning Problems (519); Linked
Comprehension Type Questions (530) ..

(xi)

·.'·353~565

10.1 Introduction (533); 10.2 Nomenclature (533); 10.3 Isomerism (534); lOA General Methods
oL.Preparation (534); 10.5 General Characteristics of Ethers (537); 10.6 Diethyl Ether or Ethoxy
Ethane (541); 10.7 Epoxides (Oxiranes)(544);10.8 Crown Ethers (545); Summary (546); Questions
(548); Answers (553); Objective Questions (554); Assertion-Reason Type Questions (558); Answers
Objective Questions (559); Brain Storming Problems (560); Linked Comprehension Type Questions
(564).

'H56~55

ILl Introduction (566); 11.2 NomenclatUre (567); 11.3 Isomerism (568); llA General Methods of
Preparation of AldehYQes and Ketones (569); 11.5 General Characteristics (578); 11.6 Tests of
Aldehydes and Ketones (Distinction) (601); 11.7 Some Commercially Important' Carbonyl
Compounds; Formaldehyde (601); Acetaldehyde (604); Acetone (606); 11.8 POlymerisation and
Condensation (608); 11.9 Acrolein (612); Summary (613); Questions (618); Answers (627); Problems.
Based on Structure and Properties (630); Objective Questions (632); Assertion-Reason Type
Questions (643); Answers Objective Questions (644); Brain Storming Problems (645); Linked
Comprehension Type Questions (652); .

.(;66&;-712

12.1 Introduction (656); 12.2 Nomenclature (657); 12.3 Isomerism (657); 12.4 General Methods of
Preparation (658); 12.5 General Physical Properties (662); 12.6 Acidity of Carboxylic Acids (663); 12.7
General Chemical Characteristics of Fatty Acids (664); 12.8 General Tests for Carboxylic Group (669);
12.9 Formic Acid (669); 12.10 Acetic Acid (670); 12.11 Interconversions (673); 12.12 Dicarboxylic
Acids (677); 12.13 Higher Fatty Acids (677); . 12.14 Substituted Carboxylie Acids (679); Summary
(681); Questions (683); Answers (687); Problems Based on Structure and Properties (689); Objective
Questions (693); Assertion-Reason Type Questions (701); An§wers Objective Questions (701); Brain
Storming Problems (702)~ Linked Comprehension Type Questions (711).

13.1 Derivatives of Carboxylic Acids (713); 13.2 Nomenclature (714); 13.3 Acetyl Chloride (715); 13A
Acetie Anhydride (718); 13.5 Acetamide (719);.13:6 Ethyl Acetate (722)i 13.7 Urea or Carbamide
(727); 13.x FatR, Oils and Waxes (732); 13.9 Soap (735); 13.10 Non-soapy Detergents (736); 13.1 1
Waxes (738); Summary (739); Questions (743); Answers (747); Problems Baseq on Structure and
Properties (750); Objective Questions ('754); AssertionReason Type Questions (760); Answers
Objective Questions (760); Brain Storming Problems (761); Linked Comprehension Type Questions
(768).

14.1 Introduction of AliphatiC Amines (770); 14.2 Nomenclature (771); 14.3 Isomerism (772); 14A
Basic 'nature of Amines (772); 14.5 General Methods of Preparation (774); 14.6 Distinction Between
Primary, Secondary and Tertiary Amines (784); 14.7 Conversions (785); 14.8 Introduction of Cyanides
and Isocyanides (786); 14.9 Alkyl Cyanides (786); 14.10 Alkyl Isocyanides (788); 14.11 Alkyl Nitrites
and Nitro-Alkanes (790); Ethyl Nitrite (790); Nitro Compounds (790); Distinction Between Ethyl
Nitrite and Nitroethane (792); Summary (794); Questions (796); Answers (798); Objective Questions
(802); Assertion-Reason Type Questions (808); Answers Objective QU,estions (809); Brain Storming
Problems (810); Linked Comprehension TypeQuestions (815~.

15.1 Introduction (817); 15.2 Carbohydrates (817); 15.3 Monosaccharides (819); Configuration of
Monosaccharides (820); Glucose (821); Fructose (826); Comparison of Glucose and Fruetose (827);
15.4 Interconversions of Monosaccharides (827); 15.5 Disaccharides (829); 15.6 Polysaccharides
(Starch and Cellulose) (831); 15.7 Proteins and Amino Acids (832); 15.8 Nucleic Acids (839); 15.9
Funetions of Nucleic acids (842); 15.10 Lipids (843); 15.11

(xii)

Our Food (844); 15.12 Balanced Diet (846); Table of Vitamins (847); Summary (848); Questions (850);
Answers (853); Objective Questions (855); Assertion-Reason Type Questions (867); Answers
Objective Questions (868); Brain Storming Problems (869); Linked Comprehension Type Questions
(872).

Aromatic Compounds (Benzene and its Derivatives) 874-1032

16.1 Meaning of the Term Aromatic (874); 16.2 Sources of Aromatic Hydrocarbons and Aromatic
Compounds (876); 16.3 General Characteristics of Aromatic Compounds (876); 16.4 Isomerism and
Nomenclature of. Benzene Derivatives (878); 16.5 Benzene (881); 16.6 Structure of Benzene (888);
16.7 Directive Influence of Functional Group in Monosubstituted Benzene (892); 16.8 Mechanism of
Aromatic Substitution (894); ·16.9 Aromatic Hydrocarbons (Arenes) (899); 16.10 Aromatic Halogen
Compounds (910); 16.11 Aromatic Sulphonic Acids (917); 16.12 Aromatic Nitro Compounds (922);
16.13 Aromatic Amino Compounds (926); 16.14 Some Important Derivatives of Aniline (936); 16.15
Aromatic Hydroxy Compounds (938); Derivatives of Phenol (946); 16.16 Aromatic Aldehydes and
Ketones (950); Benzaldehyde (950); 1.6.17 Acetophenone (958); 16.18 Aromatic Carboxylic Acids
(959); 16.19 Some Important Aromatic Acids (963); 16.20 Effect ofSubstituents on Acid Streng;th of
Substituted Aromatic Acids (967); Some Typical Aromatic Conversions (968); Questions (978);
Answers (988); Problems Based on Structure and Properties (994); Objective Questions (997);
Assertion-Reason Type Questions (1022); Answers Objective Questions (1023); Brain Storming
Problems (1024); Link~d Comprehension Type Questions (1030).

Organi(; Compounds in the Service of Mankind. 1033-1077

17.1 Polymers and Polymerization (1033); 17.2 Classification of Polymers (1035); 17.3 Some
Important Polymers (1040); 17.4 Rubber (1043); 17.5 Molecular Mass of Polymers (1045); 17.6
Biopolymers and Biodegradable Polymers (1046); 17.7 Why Do We See Colour (1047); 17.8 Dyes
(1047); 17.9·Classification of Dyes (1049); 17. \0 Introduction to Drugs and Chemotherapy (1052);
17.11 Antipyretic and Analgesics (1052); 17.12 Antiseptics and Disinfectants (1053); 17.13 Antibiotics
(1054); 17.14 Antimicrobials (1056); 17.15 Anaesthetics (1056): 17.16 Tranquillizers (l057); 17.17
Anti-Malarials (1057); 17.18 Antacids (1057); 17.19 Anti-Histamines (1058); 17.20 Chemicals in Food
(l058); 17.21 Rocket Propellants (1059); Questions (1061); Answers (l064); Objective Questions
(1065); Assertion-Reason Type Questions (1073); Answers Objective Questions (1073); Brain
Storming Problems (1074); Linked Comprehension Type Questions (1076) . .m Problems Based upon
Structure and,Reactions of Organic C~mpounds 1078-1095 Aliphatic Compounds (1079); Some
Solved Problems (1082); Aromatic Compounds (1088); Some Solved Problems (\090). .

Multiple Matching Problems for IIT .. JEE Aspirants

1
·INTRODUCTION. TO ORGANIC CHEMISTRY

1.1 DEFINITION OF ORGANIC CHEMISTRY (HISTORICAL BACKGROUND)

A large number of organic compounds*have been discovered and isolated from natural sources by
the first quarter of nineteenth century but till then none of the organic compounds could be
prepared in laboratory. This led to believe that organic compounds followed laws. of fonuation
different from inorganIc compounds. Berzelius assumed that some vital force (life force) was
necessary to prOduce organic compounds and synthesis of these compounds iIi the laboratory was
impossible due to the absence of this vital force which only existed in living organisms. . The vital
force theory suffered the first deathblow, in 1828, when·. ,¥ohler synthesised first organic
compound, urea, in the laboratory by heating ammonium cyanate (an inorganic compound).

Heat . NH4CNO -~~) NH2CONH2 . Ammonium cyanate Urea

Undergo isomeric change, i.e., (molecular rearrangement)

Heat . [(NH4hS04 + 2KCNO ) 2NH4CNO+ K2S04] [Pb(~Oh + 2NH40H Heat) 2NH4CNO+Pb(OHh]

[NH4CI + KCNO Heat) NH4CNO + KCI] A further blow to vital force theory was·given by Kolbe, in
1845, when he synthesised acetic acid, the first organic compound, in ·laboratory from its elements
and . later by Berthelot, in 1856, who synthesised methane.

2C + H2 Electric) HC=CH Dil. H2S04) arc Acetylene HgS04

CH

3 CHO Oxidation) CH

3 COOH Acetaldehyde Acetic acid Modern definitiou of organic chemistry : Since, carbon is an
.essential constituent of all organic compounds, organic chemistry is defined as the chemistry of
carbon compounds. Simplest ~rganic compounds are those which are . composed of carbon and
hydrogen only and are called hydrocarbons. Other organic compounds maybe regarded as
derivatives of hydrocarbons obtained by replacement· of hydrogen by any other element or group.
Thus, organic chemistry may also be defined as the chemistry of hydrocarbons and their derivatives.

1.2 JUSTIFICATION OF SEPARATE STUDY OF ORGANIC COMPOUNDS

Organic compounds are studied separately because of the