02-Basic Principles of Organic Srinu - CW

JEE MAINS - VOL - IV ORGANIC CHEMISTRY - SOME BASIC PRINCIPLES & TECHNIQUES
ORGANIC CHEMISTRY - SOME BASIC

PRINCIPLES & TECHNIQUES

 NH 4CNO 
on tautomerisation
 NH 2CONH 2
SYNOPSIS
ammonium Cyanate Urea
 First organic compound prepared from its
Introduction
elements in the lab is CH 3COOH . It was
 Organic Chemistry is the branch of Chemistry
which deals with study of organic compounds. prepared by Kolbe.
 Lemery (1675) divided the natural chemical  Second organic compound prepared from its
compounds into three classes based on their elements in the lab is CH 4 . It was prepared by
sources as (a) Compounds of mineral origin (b) Berthelot.
Compounds of vegetable origin (c) Compounds
 The ability of carbon atom to form long chains
of animal origin
or rings is known as catenation.
 Lavoisier (1784) showed that all compounds
obtained from vegetable and animal sources  The element with highest catenation ability in
always contained Carbon and Hydrogen, periodic table is carbon.
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sometimes Nitrogen and Phosphorus also  Carbon is tetravalent. Tetravalency of carbon was
 In the reclassification of organic compounds proposed by Vant Haff and Label.
Berzelius (1807) introduced the new terms  Organic compounds are numerous in number
“Organic” & “Inorganic”. (almost 107 ) due to
 The word ‘organic’ has been coined from the
‘organism’ (a) Maximum catenation capacity of carbon
(b) Tetravalency of carbon
Modern definition of organic
(c) Isomerism in organic compound of carbon
chemsitry
(d) Carbon has Tendency to form multiple Bonds
 The simplest orgnic compounds containing
carbon and hydrogen only are called  The main natural sources of organic compounds
hydrocarbons while all other organic compounds are coal, petroleum, natural gas, animals and
are considered to have been derived from them. plants.
Thus, organic compounds may be defined as  Organic compounds are vital for sustaining life
hydrocarbons and their derivatives and the on earth and include complex molecules like
branch of chemisry which deals with the study of genetic information bearing DNA and proteins
hydrocarbons and their derivatives is called that constitute essential compounds of our blood.
Organic Chemistry.  Organic chemicals appear in material like
 According to the Vital Force theory, proposed clothing, fuels, polymers, dyes and medicines.
by Berzelius organic compounds were from living  Formal charge = (group number in the periodic
organisms and they were produced under the table) - (no of bonds) - (no of unshared
influence of a vital force, they cannot be prepared electrons).
in the lab artificially.
 The development of electronic theory of covalent
 Urea is the first organic compound prepared in
bonding helped organic chemistry for its modern
the lab by Wohler. Vital force theory has lost its
shape
significance after synthesis of urea by Wohler.
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ORGANIC CHEMISTRY - SOME BASIC PRINCIPLES & TECHNIQUES JEE MAINS - VOL - IV
Structure and Bonding
State of Carbon in Carbon
compounds
 The ground state electronic configuration of
carbon is 1s2 2s2 2px1 2py1 2pz0
 The excited state electronic configuration of
carbon is 1s2 2s1 2px1 2py1 2pz1
 Energy of excitation is 120 K.cal mol-1 or 501.6
KJ mol-1
 The tetravalence of carbon and the formation of
covalent bonds by it are explained in terms of its
electronic configuration and the hybridisation of
s and p orbitals
 In organic compounds carbon atom undergoes
sp, sp2 and sp3 hybridisations.
 sp3 carbon is called saturated carbon.

 sp and sp2 carbons are called unsaturated
carbons.
 Greater the s - character the lower the energy
and thus near to the nucleus i.e. orbital is smaller.
 The order of size of different orbitals is p > sp3 >
sp2 > sp > s
 The change in hybridisation affects the
electronegitivity of carbon.
 The greater the s character of the hybrid orbitals,
greater is the electronegativity
E.N of carbon with sp > carbon with s p 2 >
carbon with s p 3
% S character  electronegativity of carbon
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 Determination of bond pairs : Number of bp =

 In  (pi) bond formation, parallel orientation of Number of atoms present on central atom of the
the two ‘P’ orbitals on adjacent atoms is species or number of sigma bonds present on
necessary for a proper sidewise overlap central atom of the species.
 In H2C  CH 2 molecule. The ‘P’ orbitals Determination of lone pair of
mutually parallel and both the p orbitals are electrons
perpendicular to the plane of the molecule. Number of lp’s can be determined as follows:
Rotation about C - C double bond in C = C is re i) If carbon has pi bond (s) or positive charge or
stricted. odd electron, then lp on carbon will be zero.
Determination of Hybridisation in ii) If carbon has negative charge, then lp will be
Organic Compounds equal to one.
Hybridisation in organic compounds can be Number of electron pairs tells us the type of
known by follwoing two methods: hybridisation as follows:
A) First method : ep hybridisation ep hybridisation
Number of pi bonds types of hybridisation 2 sp 5 sp3d
2
Zero sp3 3 sp 6 sp3d2
One sp2 4 sp3 7 sp3d3
Two sp Examples:
C H3  C H  C H  C  C C H3 

SP3

SP 2

SP 2

SP

SP

SP3
H 2C  C H

bp  2
B) Second method: Electron Pair method lp  0
ep = bp + lp i) 
where ep  2, sp
ep = electrons pair present in hybrid orbitals
bp = bond pair present in hybrid orbitals
lp = lone pair electrons.
 H|
H 3C  C H  CH 3 H CO  N O
 |
bp  3
lp  1 H
ii)   Final structure
Atom which have fewer electrons than 8 use
ep  4, sp 3
unshared pairs on adjacent atoms to form doubtle

or triple bond to complete the octet.
HC  C It is most stable structure for methyl nitrite

bp  1
lp  1
because
iii)        hydrogen atoms have duplet and all other atoms
have octet
ep  2, sp
H
|
H  C O  N  O
|

H 3C  C  CH 3 H
|
CH 3  calculation of formal (+ve and -ve ) charges
bp  3
lp  0
methyl nitrit has two resonance structures
iv)       
H
ep  3, sp 2 |
H  C O  N  O
|
Writing systematic lewis structures H
 The molecular formula of methyl nitrite is
CH 3 NO 2 . H
| +
H  CO  N O
 All hydrogens are connected to C - atom and |
(M) (T)
the order of atomic connections in the above H
example is CONO structure - I
 Total valence electrons can be counted as : structure - II
H  1 3  03 In the structure-I. there are no formal charges
C  4 1  04 and in
structure-II there are formal charges.the
O  6  2  12
structure -I
N  5 1  05 with no formal charges its more stable than the
------ structure -II with formal charges
24
Formula
------
 Ist partial structure Formal charge, Q f = GN - No. of bonds - No.
6bonds (shared pairs ) equivalent to 12 electrons of unshared electrons
H In the structure - II
|
H  C O  N  O
|
The formal charge on oxygen atoms
H T=6 - 1 - 6 = -1, M=6 - 3 - 2 = +1
 2nd partial structure formal charge on nitrogen atom = 5-3-2=0
provision of an octet for all atoms (exept
hydrogen atom) by using remaining 12 electrons

structural representation of organic Examples of bond line structures

molecules
1. Structures of organic compounds are represented
in several ways. The Lewis structure (or) dot 1. 2. 3 .
structure, dash structure, condensed structure and
bond line structure.
2. Example of complete structural formula
H H H
| | | ..
H  C C H H  C O  H
| | | ..
H H H
3. Examples of condensed structural formula
4. 5.
CH3 CH 3 H2C  CH 2 HC  CH CH 3OH
(ethane) (ethene) (ethyne) (methanol)
similarly CH 3CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3
can be further condensed to CH 3  CH 2 6 CH 3
4. Example of bond line representation
5. The various ways of representing 2 - bromo

butane are: 6.
Br
|
CH 3 CH CH 2 CH3
or
7.
6. In cyclic compounds, the bond - line formulas

may be given as follows

Classification of Organic Compounds
Organic compounds
Acyclic or Open Cyclic or Closed chain

chain compounds or Ring compounds
Saturated Un saturated Homocyclic or Heterocyclic

hydrocarbons hydrocarbons Carbocyclic compounds
compounds
Alicyclic Aromatic Aromatic Non- Aromatic

compounds compounds compounds compounds
Benzenoid Non-Benzenoid
compounds compounds
Cyclic compounds
Acyclic Compounds contains atleast one ring or closed chain of atoms.
these are of two types.
Organic compounds in which all the carbon atoms
are linked to one another to form open chains Homocyclic compounds
(straight or branched) are called acyclic or open cyclic compounds in which the rings are made
chain compounds. up of only one kind of atoms are called
Saturated: homocyclic compounds. However, if all the
atoms in the ring are carbon atoms, they are called
carbocyclic compounds. These are of two types:
CH 3
CH 3CH 2 CH 2 CH 3 | Alicyclic compounds.
CH 3  CH  CH 3 Carbocyclic compounds which resemble
Butane
Iso butane aliphatic compounds in most of their properties
are called alicyclic compounds. For example,
Unsaturated
CH3 CH 2 CH  CH 2
1  Butane
Cyclo propane Cyclo butane
CH 3
|
CH3  C  C  CH
|
CH 3 Cyclohexene
3,3  Dimethyl  1  butyne
b) Aromatic compounds. (b) Aromatic heterocyclic compunds :

Compounds which obey Huckel rule (i.e., Heterocyclic compunds which resemble benzene
and other aromatic compunds in most of their
 4n  2   -delocalised electrons, where properties are called aromatic heterocyclic
n  0,1, 2,.....etc ) are called aromat ic compunds. For example.
compounds. these are of two types
i) Benzenoids. Aromatic compounds and their
alkyl,alkenyl derivatives which contain one or
more benzene rings either fused or isolated in their
molecules are called benzenoids.
Benzene Naphthalene
N
Pyridine
Homologus series
 A series of organic compounds containing same
functional group and show similar properties but
Anthracene differ from the preceding one by CH2 unit.
Phenanthrene  The different members of a homologous series
are called homologues and the phenomenon is
ii) Non-benzenoids called homology.
Aromatic compounds which do not contain a 1. Homologues can be prepared by similar
benzene ring but instead contian other highly methods.
unsaturated rings are called non-benzenoids. For 2. Homologues show similar properties.
example, 3. Homologues show gradation in their physical
properties.
4. Successive members differ by a CH2 group in
molecular formula and molecular weight by 14
5. All homologues have the same general formula
Name of series General formula First member
Azulene Tropone Cyclohepta- Alkane Cn H2n +2 CH4 Methane
Alkene Cn H2n C2H4Ethylene
trienyl cation Alkyne Cn H2n -2 C2H2 Acetylene
Heterocylcic compounds Alkyl halide Cn H2n+1 X CH3 X Methyl
Cyclic compounds containing one or more halide
heteroatoms (e.g. O, N, S, etc.) in their rignhs Alchol CnH2n +1OH CH3OH Methyl
alcohol
are called heterocyclic compunds. These are of carboxylic acid CnH2n+1COOH HCOOH Formic
two types: acid
(a) Alicyclic heterocyclic compunds: Heterocyclic Nomenclature of carbon compounds
compunds which resemble alophatic compunds General Rules for IUPAC
in their propeties are called alicyclic heterocyclic Nomenclature
compunds. For example. IUPAC names usually consists of three parts (or
in many cases two parts) (1)Root word (2) Suffix
O (es) (3) prefix(es)
N Root Word :It represents the number of carbon
O x ir a n e atoms in the chain. For chain C1 to C4 special
H root words are used and for chains C5 onwards
A z ira n e , names of Greek numericals are used

No. of carbon atoms in the Root Word No. of carbon atoms Root Word longest chain
in the longest chain
1 Meth 11 Undec
2 Eth 12 Dodec
3 Prop 13 Tridec
4 But 14 Tetradec
5 Pent 20 Eicos
6 Hex 30 Triacont
7 Hept 40 Tetracont
8 Oct 50 Pentacont
9 Non 60 Hexacont
10 Dec 100 Hect/Cent
Note : The generic word for a carbon chain is alk

2) Suffix : The suffix may be
a) Primary suffix and b) secondary suffix.
a) Primary suffix : It indicates the nature of carbon chain i.e., saturated or unsaturated
Root word Pre- suffix Name
Saturated Alk -ane Alkane (eg: ethane )
Unsaturated Alk -ene Alkene (eg : ethene)
- C  C- Alk -yne Alkyne

(eg : ethyne)
If there are more than one C = C or C  C , the terms di, tri and tetra etc . are used before the primary suffix . In case
of more than one C = C or -C  C - modification of root word takes place
No. of carbons Normal root wordModified root word
4 But-` Buta-
5 pent- penta-
6 hex- Hexa-
For example :
4 3 2 1
CH2=CH- CH= CH2
IUPAC name : 1, 3 butadiene
b) Secondary suffix: It represents the functional group present in the organic molecule . This is added to a primary suffix
. The final 'e' in the primary suffix is dropped for a secondary suffix beginning with a vowel (a, e, i, o, u ) but it is retained
for a secondary suffix beginning with a consonant.
Compound Root word Pri suffix Sec- suffix Generic name
Alcohol (saturated) Alk an ol Alkanol
Alcohol (unsaturated, C = C ) Alk en ol Alkenol
Alcohol (unsaturated, C  C ) Alk yn ol Alkynol
Aldehyde (saturated) Alk an al Alkanal
Ketone Alk an one Alkanone
Carboxylic acid (saturated) Alk an oic acid Alkanoic acid
The secondary suffixes used for some important functional groups are listed below

Class Functional group Secondary Suffix
Alcohol -OH - ol Aldehydes -CHO - al
Ketones > C = O - one
Carboxylic acids - COOH - oic acid
Esters-COOR - oate
Acid chlorides - COCl - oyl chloride
Acid amides - CONH2 - amide
Acid cyanide C  N - nitrile
Isocyanides - NC - Carbyl amine
(3) Prefixes : These indicate the substitution of other groups (not regarded as functional groups) in place of
hydrogen atoms in the compound.
Group Prefix
- Cl chloro -
- Br bromo -
-I iodo -
-F fluoro -
- OR (ethers) alkoxy -
- NO2 nitro -
- NO nitroso -
TYPES OF CARBON AND HYDROGEN ATOMS
There are four types of carbon atoms and three types of hydrogen atoms.
i) Primary (1°) carbon : A carbon atom attached to one or no other carbon atoms.
ii) Secondary (2°) carbon : A carbon atom attached to two other carbon atoms.
iii) Tertiary (3°) carbon : A carbon atom attached to three other carbon atoms.
iv) Quaternary (4°) carbon : A carbon atom attached to four other carbon atoms.
Hydrogens attached to primary, secondary and tertiary carbon atoms are termed as primary,
secondary and tertiary hydrogen atoms respectively.
secondary (2o )
CH 3 CH 3 primary (1o )
CH 3  C CH  CH 2  CH 3
CH 3 Tertiary (3o )
Quaternary (4o )
Total number of 1° hydrogen atoms : 15

Alkanes : Alkanes or paraffins are saturated hydrocarbons. The general formula : Cn H2n+2. The word
'alk' indicates the chain length while the suffix 'ane' indicates saturation.
Molecular formula IUPAC name
CH 4 Methane
C2 H 6 Ethane
Alkyl groups : They are monovalent groups obtained by removing one hydrogen atom of alkanes. They
are generally represented by R-. Alkyl groups are named by replacing the suffix - '-ane' of the corresponding
alkane by -yl. General formula of alkyl group is CnH2n+1. Common names and formula of some alkyl
groups are given in the table- (8)
Common and IUPAC names of alkyl groups

Parent Formula of alkane Alkyl group Common IUPAC
alkane (R–H) (R–) name name as substituent
Methane CH4 CH3 – Methyl Methyl–
Ethane CH3–CH3 CH3–CH2 – Ethyl Ethyl–
Propane CH3–CH2–CH3 CH3–CH2–CH2 – n- Propyl Propyl–
CH3–CH–CH3 Isopropyl Methylethyl–
|
Butane CH3–CH2–CH2–CH3 CH3–CH2–CH2–CH2 – n-Butyl Butyl–
CH3–CH2–CH–CH3 sec- Butyl 1-Methylpropyl–
|
Isobutane CH 3  CH  CH 3 CH 3  CH  CH 2  Isobutyl 2-Methylpropyl–
| |
CH 3 CH 3
CH 3
|
CH3  C 
| tert-Butyl 1, 1–Dimethylethyl–
CH 3
Alkenes
 Unsaturated hydrocarbons with double bond are called alkenes or olefins.
 General formula of alkenes is CnH2n. Suffix for alkenes is 'ene'. Longest carbon chain containing the >C
= C < group is chosen.
 Numbering of the chain is done in such a way that doubly bonded carbon get minimum number.
 The compound is then accordingly named. Names of some homologous series are given below :
Formula Common Name IUPAC Name
 Cn H2n Alkene
 C2H 4 Ethylene Ethene
 C3H 6 Propylene Propene
Alkenyl group : The group derived from an alkene by removing a hydrogen atom is called alkenyl
group.
Formula Common name IUPAC Name
 CH2 = CH - Vinyl Ethenyl
 CH2 = CH- CH 2  Allyl Propenyl
 C4H 7 - Butenyl
Alkynes :
 Unsaturated hydrocarbons with - C  C - are called alkynes.
 General molecular formula of alkynes is
CnH 2n-2.

 In common system, they are named as derivatives of acetylene ( H - C  C - H), the first member of the
series.
 In IUPAC system, they are called alkynes, the suffix - ane from alkane is replaced by - yne.
 Cn H2n-2 Alkyne
 C2H 2 Acetylene Ethyne
 C3H 4 Methyl acetylene Propyne
Alkynyl group :
 The hydrocarbon residue derived by removing a hydrogen atom from an alkyne is called alkynyl group :
 CH  C - Acetylide Ethynyl
 CH  C - CH2- Propargyl Propynyl
Alkyl halides :
 The carbon compounds obtained by the replacement of one or more hydrogens of a hydro carbon by
corresponding number of halogen atoms are known as halogenated hydrocarbons.
 Depending on the number of halogens in the molecule they are further divided into mono, di, tri, polyhalogen
derivatives.
 Monohalogen derivatives of alkanes are called alkyl halides. General molecular formula is Cn H2n+1 X or
R - X. In IUPAC system they are given the name halo alkane.
Alkyl halides and IUPAC names
Alcohols :
 In IUPAC system, the alcohols are called alkanols, i.e. by replacing -e from the name of alkane by -ol i.e.,
(Alkane -e+ol=Alkanol)
 Aliphatic hydrocarbons with -OH functional groups are called alcohols.
 General formula is Cn H2n+1 OH.or R - OH
 CH 3  OH Methyl alcohol, Woodspirit, Carbionol Methanol
 CH 3CH 2  OH Ethyl alcohol, Grain, Alcohol, Spirit of wine Ethanol
 CH 3CH 2CH 2  OH n- propyl alcohol Propanol
 CH 3CH 2 CH 2CH 2  OH n - butyl alchol Butanol
 CH 3  CH  CH 2  OH Sec - butyl alcohol 2- Butanol

|
CH 3
CH3
|
 CH 3  C  OH t - butyl alcohol 2 - Methyl - 2- Propanol

|
CH3
Ethers :
 IUPAC name of ether is alkoxy alkane.
 The smaller alkyl group plus the oxygen atom is called as an alkoxy substituent.
 The name of the alkane is prefixed by the name of the alkoxy group and position number.
 General formula is (CnH2n+1)2O.
Formula Common name IUPAC name
CH3OCH3 Dimethyl ether Methoxy methane
CH3OC2H5 Methyl ethyl ether Methoxy ethane
C2H5OC2 H5 Diethyl ether Ethoxy propane
C2H5OCH (CH3)2 Ethyl isopropyl ether 2- Ethoxy propane
Aldehydes
 In IUPAC system , aldehydes are named after the corresponding alkanes suffix-'ane' is replaced by
the suffix - al.
When substituents are present ,the carbonyl carbon is assigned no.1.
General formula is Cn H2nO
Aldehydes contain - CHO functional group
Formula IUPAC name Common Name
H - CHO Methanal Formaldehyde
CH3 -CHO Ethanal Acetaldehyde
CH3 - CH2-CHO Propanal Propionaldehyde
 CH3- CH2- CH2-CHO Butanal n- Butyraldehyde
CH 3  C H  CHO
 | 2 - Methylpropanal Iso-Butylaldehyde
CH3
Ketones
 In IUPAC system longest chain containing the ketonic group is taken as the parent chain.
 In naming the ketone corresponding to the chain, the following procedure is adopted.
 Root word -e+ one i.e , alkanone. In ketones >C= O group is present.
 In ketones the carbonyl carbon is linked with two alkyl groups.
 The general formula is (Cn H2n+1)2 CO or R 2 CO.
Formula Common Name IUPAC name

CH3 CO CH3 Acetone Propanone
CH3 -COCH2CH2CH3 Methyl Propyl ketone 2 -Pentanone
CH3- CH2-CO CH2 CH3 Diethyl ketone 3 - Pentanone
CH2 = CH - CO-CH3 Methylvinyl ketone 3-Butene -2-one
Carboxylic acids
 In IUPAC system acids are named as alkanoic acids (alkane -oic - acid).
 The name is derived by replacing 'e' of the corresponding alkane by -oic acid.
 General formula is R-COOH or Cn H2n+1 COOH
H-COOH Formic acid Methanoic acid
CH3-COOH Acetic acid Ethanoic acid
CH3 -CH2-COOH Propionic acid Propanoic acid
CH3 -CH2 -CH2 -COOH Butyric acid Butanoic acid
CH3 -CH2 -CH2-CH2-COOH Valeric acid Pentanoic acid
Acid chlorides:
 IUPAC name is alkanoyl chloride.
 It is derived from the corresponding alkane by replacing 'e' with 'oyl' halide.
 General formula is R- COCl . Cn H2n+1 COCl
H- COCl Formyl chloride Methanoyl chloride
CH2- COCl Acetyl chloride Ethanoyl chloride
CH3 -CH2 - COCl Propionyl chloride Propanoyl chloride
Amines :
 Aliphatic amines are the alkyl derivatives of ammonia .
 Monoalkyl derivatives of ammonia are called primary amines, (R - NH2).
 Dialkyl derivatives of ammonia are called secondary amines, (R - NH-R).
 Trialkyl derivatives of ammonia are called tertiary amines (R3 - N).
 IUPAC name of primary amine is amino alkane, secondary amine is N - alkyl amino alkane and tertiary
alkane is N, N-dialkylamino alkane.
Primary amines
CH3 -NH2 Methylamine Aminomethane or Methanamine
CH3 -CH2 -NH2 Ethyl amine Aminoethane or Ethanamine
CH3 -CH2 -CH2 -NH2 n - propylamine 1- Aminopropane or 1-propanamine
Secondary amines
CH3 - NH- CH3 Dimethyl amine N - methyl aminomethane or
N- methyl methanamine
CH3 -CH2-NH- CH3 Ethyl methyl amine N -methyl aminoethane or
N-methyl ethanamine
CH3 -CH2 CH2 -NH -CH3 Methyl propylamine N -methyl amino propane
Tertiary amines
(CH3)3 N Trimethyl amine N, N-dimethyl - aminomethane
(CH3)2 NC2 H5 Dimethyl ethyl amine N, N-dimethyl - aminoethane
(CH3)2CH - CH2 N(CH3)2 Dimethyl isobutylamine N, N- dimethyl - 2 - methyl -
1-propanamine

Nitro compounds :
 The functional group is - NO2. If 'N' of -NO2 is linked to the alkane it is named as nitro alkane.
 If 'O' of - NO2 group is linked to the alkane it is named as alkylnitrate
Formula Common Name IUPAC name
CH3.NO2 Methylnitrate Nitromethane
C2H5.NO2 Ethylnitrate Nitroethane
C3H7.NO2 Propylnitrate Nitropropane
NOMENCLATURE OF BRANCHED CHAIN ALKANES
 To sum of IUPAC name of an organic compound consists of following arragement word-root suffixes and
prefixes.
IUPAC NAME = 20 prefix + 10 prefix + word root + 10 suffix + 20 suffix.
2 3
1 4
O Br
For example ,
6 5
4 Bromo + Cyclo + Hex + an(e)* + 1-one = 4 - Bromocyclohexan - 1 - one or 4-

(20 prefex) (10 prefix) (Word (10 suffix) (20 suffix) Bromocyclo - hexanone
root) (IUPAC name)
I) longest chain rule
 The longest continuous chain of carbon atoms in the molecule is selected as a root word
1 2 3
CH3 - CH2 - CH -CH2 -CH3
|4 5 6
CH2 - CH2 - CH3
correct selection ( 6 C atoms)
1 2 3 4 5
CH3 - CH2 - CH - CH2 - CH3
|
CH2 - CH2 - CH3
wrong selection (5 C atoms)
 If two different chains of equals lengths are possible , the chain with maximum number of side chains or
alkyl groups is selected. For example:
1 2 3 4
CH 3  CH 2  CH  CH  CH 2  CH 2  CH 3
| |5 6 7
CH 3 CH  CH  CH 3
|
CH 3
correct selection (Longest chain of 7C atoms with three branches)
1 2 3 4 5 6 7
CH 3  CH 2  CH  CH  CH 2  CH 2  CH 3
| |
CH 3 CH  CH  CH 3
|
CH 3
wrong selection (Longest chain of 7C atom with two branches)

II. Lowest number or lowest sum rule.

 Numbering of the carbons in the parent chain as 1, 2, 3..... etc. starting from the end which gives the least
number to the carbon atoms carrying the substituent (S).
S
4 3 |2 1
C - C - C - C,
(correct)
S
1 2 |3 4
C-C- C- C
(wrong)
When several substituents are involved, the lowest number means (i) lowest sum of numbers (ii) lowest
individual numbers (iii) lowest number for the first named group, in the order of preference.
S S S
| | |
C C C C C C C
1 2 3 4 5 6 7
2+5+6 =13 ( wrong numbering)
S S S
| | |
C C C C C C C
7 6 5 4 3 2 1
2+3+6 = 11 (correct numbering)
III. Presence of more than one substituents
 If the same substituent is repeated in the chain that is indicated by prefixes such as di, tri, tetra etc. indicate
number of such groups or atoms
CH3
|
H3 C - C - CH3
|
CH3
( 2, 2 dimethyl propane)
IV. Alphabetical order
 If two or more substituents are present on the parent chain , they are named in the alphabetical order along
with their appropriate positions.
CH3 CH2 - CH3

1 |2 3 |4 5 6 7
H 3 C -C H - CH2 - CH - CH2 - CH2 - CH3
4 -ethyl - 2 methyl heptane
V. Numbering of carbon atoms
 Alkyl group substituents containing sub branch substituted alkyl groups are named as substituted alkyl
groups.

 The numbering is done as shown below:  If the parent chain is hydrocarbon it includes both
CH 3  CH 2  CH 2  CH 2  CH  CH 2  CH 2  CH 2  CH 3 'ene' and 'yne'. Then the orders of preference
1 3 4 |5 6 7 8 9
2 'ene' > 'yne'
1' CH 2
|
CH 3  C ' CH 3 HC  C - CH 2 - CH = CH2
|2
3' CH 3
5 4 3 2 1
pent -1- en-4 -yne
5-(2', 2' -dimethylpropane) nonane
 Priority Principle: If the compound is poly
VI. If two equally long chains are possible, the chain
functional compound, the selection of the
with maximum number of side chains is selected
principle functional group follows the sequence.
as parent chain.
Acids > acid derivatives except nitriles > nitriles
CH 3 > aldehydes > ketones > alcohols > amines >
| ether ``> double bond > triple bond.
CH 3  C  CH 3 Examples .
eg : | C2 H5
CH 3  CH 2  CH  CH 2  CH 3
|
3–Ethyl–2, 2–dimethyl pentane. 1. CH3 - CH2 - C = CH- CH3
Nomenclature of Organic compounds 3 - ethyl pent - 2- ene
containing functional group
C2 H5
COOH  SO3 H  COOR  |
COCl  CONH 2  CN  CHO  2. CH2= CH-CH-CH=CH2
Pripority order : CO  OH  SH  NH 2  OR  3 - ethyl pent- 1,4 - diene
N  N  NO2  NO  X CH3 CH3
| |
. The longest parent carbon chain is selected in 3. CH3 -CH -C  C - CH -CH3
such a way as to include in it. 2,5 - dimethyl hex -3- yne
Ex: CH3
|
CH 3
| 4. CH  C-C- CH = CH2
CH 2 |
5 4 3 |2 1 CH3
H 3C - H 2 C - H 2 C- C = CH 2 3,3 - dimethylpent -1- en - 4 -yne
correct chain CH3
|
Ex:
5. CH3 - C -CH = CH -CHO
|
6 CH 3
| CH3
5 CH 2 4, 4 - dimethyl - 2- pentenal
1 2 3 |4
H 3C - H 2 C - H 2 C- C = CH 2 6. CH3 - CH2 - CH - CH3
Wrong chain |
OH
 The numbering of atoms in the parent chain is
2 - butanol
given in such a way that carbon atoms containing
functional group gets the lowest number.

7 HC  C - CH2 OH 19 CH3 -CH2 -O -CH2 - CH2 Cl

2 - propynol or prop - 2- yn- 1- ol 2 - chloro -1- ethoxy ethane
CH3
| 20 CH3
8 CH3 -C- CH2- CH - CH3 |
| | CH3 -O - C- CH3
CH3 OH |
4, 4- dimethyl pentan -2-ol CH3
9 CH3- CH - CH - CH2- COOH 2 - methoxy -2- methyl propane
| | Writing the structure of the
CH3 OH
compound whose name is given
3 - hydroxy - 4 methyl pentanoic acid
 Observe the root word and write the continuous
10 CH3 - CH2 -CH = CH. COOH
carbon chain.
pent 2- enoic acid
 Number the carbon atoms in a suitable way and
11 CH3 - CH - CH2 -CHO
attach the functional groups, substituents and
|
multiple bonds at their respective carbon atoms.
OH
 Carbon has tetravalency. Attach the required
3 - hydroxy butanal
number of hydrogen atoms at each carbon atom
12 CH3 - CH = CH- CHO
to satisfy its tetra valency. Now the structure is
2 - Butenal
completed.
CH3 CH3
Example :
| |
13 CH3- CH - CH - CH2 - C  N 3  Bromo  2  Methyl pentan  2  ol
3,4 - dimethyl pentane nitrile a) As per the word root pent we have
14 CH3 -C - CH2 - C -CH3 1 2 3 4 5
C C C C C
|| ||
O O OH
pentane - 2,4 -dione |
1 2 3 4 5
25 CH3 - CH2 - CH -CH2 - COCH3 CC C CC
b) As per the name | |
| CH 3 Br
NH2
4- amino 2- hexanone c) To satisfy the tetravalency of each carbon atom
16 CH3 -C -CH = CH2 hydrogen atoms ate added to each carbon atom
|| as per requirement.
O H OH H H H
but 3- ene- 2- one | | | | |
17 CH3 - CH2 -CH -COOC2 H5 H C C C C C  H
| | | | |
| H CH 3 Br H H
CH3
ethyl 2- methyl butanoate Hence, the structure is complete.
Cl Rules for IUPAC nomenclature of alicyclic
| compounds
18 CH3 - CH - CH - CH3 The follwoing rules are generally followed.
|  The names of alicyclic compounds are obtained
CN by adding the prefix ‘cyclo’ to the name of the
3 - chloro -2- methyl butanenitrile corresponding straight chain hydrocarbon
(alkane, alkene or alkyne).
Cyclobutane
Cyclohexene Cyclohexyne
 If two or more alkyl groups or other substituent groups are present in the ring. their positions are indicated
by arabic numerals, i.e., 1, 2, 3, 4,... etc. While numbering the carbon atoms of the ring, the substitutent
which comes first in the alphabetical order is given the lowest number provided it does not violate the
lowest locant rule. For example,
1
1 2 6 2
5 2 3 1
3
5
4 3 4 5 4
1, 2-Dimethylcyclopentane 1-Ethyl-2-methyl cyclohexane 3-Ethyl-1,1-dimethyl cyclohexane
 If the ring contans more or equal number of carbon atoms as the alkyl group attached to it, it is named as
a derivative of cycloalkane and the alkyl group is treated as a substituent group, otherwise it is named as a
derivative of alkane and the cycloalkyl group is considered as a substituent group. For example.
Hexyl cycloexane
1- (2-Butyl) cyclohexane 2-Cyclopropylpentane
 If, however, the side chain contains a multiple bond or a functional group, the alicyclic ring is treated as the
substituent irrespective of the size of the ring. Exampl.
NO 2
2
3
3 1
2
4 5 1
3 -Cy clopropylprop -1-ene 1,5-Dimethylcyclopent-1-ene 3-Nitrocy clohex-1-ene

Nomenclature of Bicyclo Compounds: of the compound with the principal funcitonal

 Many Hydrocarbons and the derivatives contains group at position.
two fused rings. The Carbon atoms common to  If all the functional groups present in the benzene
both rings are called bridge head atoms and each ring are such which are normally treated as
bond or chain of carbon atoms connecting both substituent groups, the various groups are
the bridge head atoms is called as bridge. The arragned in alphabetical order with the group
bridge may contain 0, 1, 2 ..., etc carbon atoms. named first in the alphabetical order getting the
 These bicyclic compounds are named by lowest locant provided it does not violate the
attaching the prefix ‘bicyclo’ to the name of the lowest locant rule for all the substitutents.
hydrocarbon having the same total number of
carbon atoms as in the two rings. The number of
carbon atoms in each of the three bridges
connecting the two bridge head carbon atoms is
indicated by arabic numerals, i.e., 0, 1, 2... , etc.
These arabic numerals are arranged in
descending order ; separated from one another
bhy full stops and then enclosed in square Methylbenzene Met hoxybenzene
brackets. The complete IUPAC name of the Bromobenzene
hydrocarbon is then obtained by placing these
square brackets containing the arabic numerals

between the prefix bicyclo and the name of the
alkane. For example:
1, 2-dibromobenzene 1, 2-dichlorobenzene
1-chloro-4-nitro Benzene Benzene

benzene carbaldehyde carboxylic acid
 If a substituent is present, the bicylic ring system
is numbered. The numbering beings with one of
the bridge head atoms.
Nomenclature of Aromatic Compounds:

 When an aromatic compound contains two or 1, 2-dimethyl hydroxy benzene Acetophenone
more functional groups, it is named as a derivative benzene
 Substituent of the base compound is assigned give the lowest locant at the first point of
number 1 and then the direction of numbering is difference.
chosen such that the next substituent gets the
lowest number. The substituents appear in the
name in alphabetical order.
example
Example :
4-ethyl-1-fluoro-2-nitrobenzene
Consider
 If benzene ring is named as substituent it is named
as phenyl  C6 H 5  . Similarly an arene is named
It is named as 2, 4, 6 - trinitro toluene taking
toluene as the base name. as aryl.
Similarly is named as
4-ethyl - 2 - fluroanisole. 2-phenylethanol

chloro phenyl methane
(Benzyl Chloride)
 When no simple base name other than benzene STRUCTURAL ISOMERISM
is possible, the positions are numbered so as to Isomerism
 The existence of two or more compounds with
the same molecular formula is known as
isomerism. The different compounds are known
as isomers .Isomerism is classified into two types
namely structural isomerism and Stereo
isomerism

Structural isomerism 1- Butene 2- Butene

 When the isomerism is due to difference in the CH3-CH2-C  CH and CH3 - C  C- CH3
arrangement of atoms with in the molecule, 1-Butyne 2-Butyne
without any reference to space, the phenomenon The above pairs are examples for position
is known as structural isomerism. isomers
 In this type of isomerism, the isomers possess
CH 3 CH 3 CH 3 CH 2Cl
the same molecular formula but different structural
formula. Cl
Chain Isomerism
1. Chain isomerism arises due to difference in Cl
o-chloro Toluene
the arrangement of atoms in the carbon chain. m-chloro Toluene Benzyl chloride
Cl
2. For a substance to show chain isomerism it p-chloro Toluene
must contain at least four carbon atoms
The above are the Examples for position isomers
3. Butane has two chain isomers namely n-Butane
& iso butane . Cl Cl Cl
4. Pentane has 3 chain isomers namely n-
Cl
pentane,isopentane and neopentane .
5. As the number of carbon atoms increases the
number of chain isomers increases.
Cl
6. Ethyl benzene and xylenes are chain isomers o-dichloro Benzene m-dichloro Benzene
Cl
p-dichloro Benzene
Alkane No. of possible isomers
The above are the Examples for position isomers
C4 H10 2 Functional Isomerism
C5 H12 3 Functional isomerism arises due to difference in
the functional group.
C6 H14 5 C2 H5 OH & CH3- O -CH3
C7 H16 9 ethyl Alcohol Dimethyl Ether
C8 H18 18 O
C9 H 20 35 CH3-CH2 -CHO & C H 3  C  CH 3

C10 H 22 75 Propanaldehyde Acetone
CH3-COOH & HCOO-CH3
Positional Isomerism Acetic acid Methyl Formate
 Positional isomerism arises due to difference in The above pairs are examples for functional
the position of a substituent (or) C = C (or) C isomers
 C bond or functional group  Functional isomerism is shown by genarally
A. Alcohols - Ethers
OH B. Aldehydes - Ketones
C. Carboxylic acids - Esters
CH3-CH2-CH2- OH CH 3  CH  CH 3 D. Cyanides and Isocyanides
1-propanol 2- propanol CH 3CN - ethane nitrile, CH 3 NC -methane
(n- propyl alcohol) (isopropyl alcohol) isonitrile
CH3- CH2- CH = CH2 and CH3- CH = CH -
CH3
E. Nitroalkanes and alkyl nitrites : Ring Chain Isomerism
CH 3 NO2 - nitro methane, CH 3ONO - methyl  If one isomer has open chain structure and the
nitrite other has cyclic structure then isomers known as
F. Alkadiene and alkyne ring chain isomers and the isomerism is
Ring chain isomerism
: C H 2  C H  CH  C H 2  1, 3  butadiene ,
Ex:-
CH 3  C  C  CH 3  2-Butyne
1. CH 3  CH 2  C  CH and
G. Primary, secondary and tertiary amines
CH 3  CH 2  CH 2  NH 2 CH 2  CH
CH 3  CH 2  NH  CH 3 CH 2  CH
1-amino propane N - methyl, amino ethane
2. CH 2  CH  CH 2OH and
 CH 3 3 N
N, N - dimethyl amino methane CH 2  CH 2
H. Alcohol and phenol
CH 2  O
phenyl methanol 2-methyl phenol

3. CH 3  CH  CH 2 and
I. Glucose and Fructose are functional group
c y clo p ro p an e
isomers
C6H 12O 6 & C6H12O6 Ring chain isomers are always functional isomers
Glucose [Aldehyde] Fructose [Ketone] Tautomerism
Metamerism:  Tautomerism is a phenomenon in which a single
 Isomerism arises due to the difference in nature compound exits in two readily inter convertable
of alkyl groups attached to the same functional structures that differ in the relative position of at
group is called metamerism and such isomers are least one hydrogen. The different structures are
called metamers. Metamerism is exhibited by known as tautomers
ethers, ketones, sec- amines, esters and  Some times the term tautomerism is also called
anhydrides as desmotropism (greek desmos -bond, tropos-
1. C5 H10 O (two metamers) turn), since the interconversion of the two forms
involves a change of bonds or dynamic isomerism
H 3C  CH 2  C  CH 2  CH 3 H 3C  C  CH 2  CH 2  CH 3
as the two forms are in dynamic equilibrium with
O O each other. Tautomerism is other wise called as
kryptomerism, allelotropism or merotropy
diethyl ketone methyl, n - propylketone
There are several types of tautomerism of which
(3- pentanone) ( 2 -pentanone)
keto-enol tautomerism is the most important
 C4 H10 O(three metamers) It is caused by the wandering nature (1,2 or
mainly 1,3 migration) of mobile hydrogen atom
C2H5  O  C2H5 CH3  O  CH2  CH2  CH3 between two polyvalent atoms within the same
(diethyl ether ) 1methoxy propane molecule.
If the hydrogen atom oscillates between two
CH 3O  CH  CH 3
|
polyvalent atoms linked together, the system is a
CH3 dyad and if the hydrogen atom travels from first
(2methoxy propane ) to third in a chain, the system is a triad.
 Hydrocyanic acid is an example of dyad system

O OH
in which hydrogen atom oscillates between
carbon and nitrogen atoms.
H – C N C N–H
Triad system 7. 
i) Keto–enol system (Keto-enol tautomerism) :
A ketone exists in equilibrium with its enol
tautomer. The two constitutional isomers are
tautomers because they differ in the location of a O
double bond and a hydrogen OH
O OH
8. 
R  CH 2  C  R  R  CH  C  R O O
(Keto) (Enol)
Tautomerism is not possible in C6 H 5CHO and
Condition for tautomerism C6 H 5COC6 H 5 because of abscence of
 For any compound to show tautomerism
 - Hydrogen.
a) Compound should have electron withdrawing
Analysis of enolic content
groups like
O
 The percentage of enolic content in the
equilibrium mixture of keto and enol form
C , N O2 ,C  N , etc.
depends on the stability of keto and enol form
b) Compound should have atleast one  -H, The stability of enol depends upon the following
i.e., H attached to  –Carbon. factors
 Examples: 1) Structural factors (Hydrogen bond,
Conjugation,Aromatisation, Stearic factor)
2) Nature of solvent
1. 3) Temperature
 Generally keto form predominates and enol form
2. is in traces because of greater strength of carbon-
oxygen double bond as compared to that of
carbon-carbon double bond.
If enol form is stabilized by intra molecular
3.
hydrogen bonding and by conjugation etc then
enol percentage increases
O
Ex:-
4. CH 2  CH  OH  CH  C  H O
3
1. CH 2  CH  OH  CH  C  H
3
5.
(Vinyl alcohol) (Acetal dehyde)
( 2  103% )
6.

CH 3  C  CH 2  C  OC2 H 5  keto form 92%  OH

|| ||
O O O


4.
OH O
| ||
(A rom atic)
CH 3 C  CH  C  OC2 H 5  Enol8% 
keto form > enol form enol form > keto form
Keto form (92%) Enol form (8%)
Double Bond Equivalents and
 Aceto acetic ester shows properties of both
ketonic group as well as enolic group. Number of Structural Isomers
Presence of keto form of aceto acetic ester is  Sometimes, the problem on structural isomerism
evidenced by the usual reactions of carbonyl can be more easily solved if we know the number
group with of Double Bond Equivalents(D.B.E.) or the
Index Number (i.e., the index of hydrogen
NH 2OH , C6 H5 NHNH2 , HCN , NaHSO3 etc.
deficiency).
Where as enolic form is evidenced by
decolourisat ion of Br2 wat er and D.B.E =
 n(v  2)  1
2
decolourisation of FeCl3 . where n = number of atoms, v = valency of the
 Analysing the acidity of hydrogen atom of active atom.

methylene group, the order of enolic content has
For example , D.B.E of C 4 H 6 is 2 as calculated
been found to be
below :
 -ketoacid<  -ketoester<  -di ketone
4(4  2)  6(1  2)
<  -ketoaldehyde D.B.E = 1
2
This is because the order of electron with
drawing effect is 860
= 1  2
-COOH<-COOR<-COCH 3  CHO 2
If D.B.E is 2, the molecule may contain :
Solvent Effect on Enol Content
(i) two double bonds or one triple bond or
 The keto form is more polar than enol form
(ii) one ring and one double bond or
therefore according to the concept of like
(iii) two rings.
dissolves like, The polar solvent favours keto
The following examples will illustrate the above
form while non polar solvent favours enol form.
rule.
Other Common Examples of Example : Write all the acyclic and cyclic isomers
Tautomerism
having the molecular formula C3H 6O ?
Solution : D.B.E =
1.
3  4  2   6 1  2   1 2  2 
1
2
2. 660
= 1  1
2
O OH Since, the D.B.E. is 1, therefore ,the isomers may
contain either adouble bond or a ring. Further
3.  since the molecular formula contains an oxygen
(non aromatic) (anti aromatic)
atom, therefore, the isomers may contain a 4. The first carbon compound prepared from
C = C or C = O double bond. If a C = C double its elements is
bond is present, then the oxygen atom must be 1) Urea 2) Acetic acid
present either as an either or as an achool. Thus, 3) Methane 4) Benzene
the various isomers are : 5. Main source of most of the organic
a. Acylic isomers are : compounds is
1) Coal tar 2) Petroleum
O
3) Both 1 & 2 4) Ammonia
6. The first organic compound was synthesized
i) C H 3  C  CH 3
in laboratory by
A c e to n e
1) Wohler 2) Kolbe
O 3) Berzelius 4) Neil Barthlot
7. The tetrahedral structure of carbon was
ii) C H 3  C H 2  C  H proposed by
Propionaldehyde 1) Kekule 2) Wohler
3) Vant Hoff and Le-Bel 4) Berthlot
iii) CH 2  CH  CH 2OH 8. The first organic compound synthesised in
the laboratory from an inorganic compound
iv) CH 2  CH  O  CH 3
is
Prop-2-en-1-ol
Methoxyethene 1) NH 4 NCO 2) NH 2  CO  NH 2
b. Cyclic isomers are : 3) CH 3COOH 4) CH 4
v) o vi) o 9. When a mixture of potassium cyanate and
CH 3 ammonium chloride is heated, it gives
Oxetane Methyloxirane 1) Urea 2) Methanmide
3) Ethanamide 4) Ethanamine
10. Organic compounds are numerous since
vii)H OH
1) Carbon has high catenation ability
2) Tetravalency of carbon
Cyclopropanol 3) Isomerism of organic compounds
4) All of these
CONCEPTUAL 11. Marsh gas mainly contains
1) C2 H 4 2) C2 H 4
INTRODUCTION 3) CH 4 4) C2 H 6
12. Which of the following contains acetic acid?
1. Organic compounds can be formed by 1) Vinegar 2) Molasses
1) Plants only 2) Animals only 3)Coal tar 4) Butter
3) Plants and Animals 4) Plants, animals and
can be synthesized in laboratory STRUCTURE AND BONDING
2. Generally organic compounds are
1) Amorphous 2) Complexes 13. Energy required for the excitation of carbon
3) Covalent 4) Electrovalent atom is
3. The vital force theory was proposed by 1) 501. 6 KJ/ mol 2) 827.0 KJ/ mol
3) 341.0 KJ/ mol 4) 610.0 KJ/ mol
1) Wohler 2) Berthlot
3) Berzelius 4) Kolbe
14. Hybridisation at 2nd carbon in 27. The total number of structural isomers for
CH2 = CH - CH3 is the compound of the formula C4 H10O is
1) sp 2) sp2 3) sp3 4) sp3d
1) 7 2) 6 3) 4 4) 3
15. Which of the following has maximum C - H
28. The number of primary alcoholic isomers
bond length
1) C2H4 2) C2H2 3) C2H6 4)C6H6 with the formula C4 H10O is
16. Which of the following is linear in shape ? 1) 1 2) 2 3) 3 4) 4
1) Methane 2) Ethane 29. The compound which is not isomeric with
3) Ethene 4) Ethyne diethyl ether is
1) n-propyl methyl ether 2) Butan-1-ol
STRUCTURAL ISOMERISM 3) 2- Methylpropan-2-ol 4) Butanone
30. The number of isomeric amines possible for
17. Number of possible position isomers for the formula C3 H 9 N
Dichlorobenzene is 1) 4 2) 3 3) 5 4) 6
1) 2 2) 3 3) 4 4) 5
18. n- Butane and isobutane are a pair of KEY
1) chain isomers 2) position isomers
3) metamers 4) functional isomers CONCEPTUAL
19. Alkanols and Alkoxyalkanes are 1) 4 2) 3 3) 3 4) 2 5) 3
1) Functional isomers 6) 1 7) 3 8) 2 9) 1 10) 4

2) Keto-enol tautomers 11) 3 12) 1 13) 1 14) 2 15) 3
3) Geometrical isomers 16) 4 17) 2 18) 1 19) 1 20) 1
4) Not isomers at all 21) 3 22) 4 23) 3 24) 4 25) 1
20. n-propyl alcohol and isopropyl alcohol are 26) 1 27) 1 28) 2 29) 4 30) 1
examples of
1) Position isomerism 2) Chain isomerism
3) Tautomerism 4) Geometrical isomerism HINTS
21. The number of structural alcoholic isomers
for C4 H10O is CONCEPTUAL
1) 2 2) 3 3) 4 4) 5
22. In the following the isomers are O
9. ||
1) Ethanol and ethoxy ethane KCNO  NH 4Cl 
 KCl  NH 2  C  NH 2
2) Methanol and methoxy methane
15. Due to Sp3  S bond
3) Propionic acid and ethyl acetone
4) Propanal and acetone 16. due to ‘sp’ hybridisation
23. Primary, secondary and tertiary amines are 17. they differ in length of carbon chain
1) Chain isomers 2) Position isomers 19. Alcohols & ethers are functional isomers
3) Functional isomers 4) Tautomers 20. due to difference in the position of - OH gruop
24. Cycloalkanes are isomeric with C  C  C  C  OH , C  C  C  C , C  C  C  OH
| |
21.
1) Alkadienes 2) Alkynes OH C
3) Aromatic compounds 4) Olefins C
|
25. Number of possible monochloro benzenes is C  C  OH
1) 1 2) 3 3) 5 4) 6 & |
C
26. Diethylether and n - propyl methylether are
1) Metamers 2) Chain isomerism 22. having same MF
3) Geometrical isomerism 4) Position isomerism 23. 10 , 20, 30 anines are functional isomers
24. Alkenes and Cyclo Alkanes are functional 8. C  C  C bond angle in benzene is about
isomers 1) 1090 28 ' 2) 1800
25. only one form is possible
3) 1200 4) 1000
26. Ethers show metamerism
27. Alcohols isomers =4 & ether isomers=3
28. C-C-C-C-OH, C-C-C-OH STRUCTURAL FORMULAE (OR)
| CARBON SKELETON DIAGRAMS
C
29. verification of moleculer formula
30. 10 , 20, 30 amines are functional isomers 9. structure is
LEVEL – I
STRUCTURE AND BONDING 1)
1. Which hybrid orbitals are involved in the

CH 3  CH  CH  CH 3 compound OH CH 3
| |
1) sp and sp3 2) sp2 and sp3 2) H 3C  CH  CH 2  CH 2  CH  CH 3
|
3) sp and sp2 4) only sp3 CH 2

2. The ratio of pure and hybrid orbitals |
CH 3
H 2C  CH  CH  CH 2
1) 7 : 12 2) 14 : 13 3) H 3C  CH 2  CH 2  CH 2  CH 2  CH 3
|
3) 12 : 10 4) 5 : 6 OH
3. The hybridisation of central carbon in
OH
CH 2  C  CH 2 |
4) H 3C  CH 2  CH  CH  CH 3
1) sp 2) sp2 3) sp3 4) all
3. Which of the following bonds is strongest?
1) 2)  C  C  10. contains how many carbon atoms
|
1) 9 2) 10 3) 11 4) 8
3)  C|  C|  4)  C  C 
5. The cylindrical shape of alkynes is due to
1)Three  C  C bonds CLASSIFICATION OF
2) Three  C  C bonds CARBON COMPOUNDS
3) Two  C  C and two  C  C bonds
11. According to Huckel’s rule a compound is
4) One  C  C and two  C  C bonds said to be aromatic if it contains
6. The number of  electrons in anthracene is 1) 4n bonds 2) 4n atoms
1) 6 2) 10 3) 12 4) 14 3) (4n+2)atoms 4)(4n+2)  electrons
7. The number of carbon atoms arranged 12. Which of the following is an aromatic
linearly in the molecule compound
CH 3  C  C  C  CH
|
2 1) Phenol 2) Naphthalene
H 3) Pyridine 4) All
1) 5 2) 4 3) 3 4) 2
13. Which is a saturated compound?
1) alkanes 2) alkenes 23. IUPAC name of CH 2OH  CH 2OH is
3) alkynes 4) cyclo alkenes 1) 1, 2 - dihydroxy ethane
14. Which is an alicyclic compound 2) Ethylene glycol
1) benzene 2) cyclohexane 3) Ethane - 1, 2- diol
3) pyridine 4) pyrrole 4) Ethane - 1, 2 - dial
15. Which of the following is not a cyclic 24. IUPAC name of CH  C  CH  CH 2 is
compound? 1) But - 3 - ene - 1- yne
1) Anthracene 2) Pyrrole 2) But - 1 - ene - 3 - yne
3) Phenol 4) Isobutylene 3) But - 1- yne - 3- ene
4) But - 3- yne - 1- ene
NOMENCLATURE OF 25. In IUPAC system of naming of organic
CARBON COMPOUNDS compounds. Which of the following functional
group has more preference than others (in
16. Functional group present in amides is a poly functional compound)
1) - COOH 2) -NH2 1) OH 2) CHO
3) -CONH2 4)- COO -
3) CO  4) CONH 2
17. O
|| 26. The IUPAC name of OH CH 3 is
| |
- C - group is present in CH 3  CH  CH 2  CH  CHO
1) ketones only 2) aldehydes only 1) 4-hydroxy -2- methyl pentanal
3) Carboxylic acid only 4) All the above 2) 2-hydroxy -4- methyl pentanal
18. Which of the following group is always 3) 4-hydroxy-2-methyl pentanol
represented by prefixes in the nomenclature 4) 2-hydroxy-4- methyl pentanol
1)  NH 2 2) CN 27. The functional group present in acylchlorides
3) CHO 4)  NO2 is
19. I.U.P.A.C name of ester is O
||
1) Cl 2)
1) Alkoxy alkane 2) Alkyl alkanoate  C  Cl
3) Alkanoyl halide 4) Alkanoic anhydride O
20. I.U.P.A.C name of methyl cyanide is 3) ||
4) CH 2  OCl
1) Cyano methane 2) Ethanenitrile  C  OCl
3) Methane nitrile 28. 3 - methyl penta-1,3- diene is
4) Methyl-n-butyl amine 1) CH 2  CH  CH 2  2 CH 3
21. The suffixes for alcohols, aldehydes and
ketones, according to IUPAC system are 2) CH 2  CHCH  CH 3  CH 2CH 3
respectively
1) -ane , - al - keto 2) -ol -al - keto 3) CH 3CH  C  CH 3  CH  CH 2
3) -al , - ol, - one 4) -ol, -al , -one 4) CH 3  C  CH  CH 3  2
22. The correct IUPAC name of
29. The structural formula of methyl amino
CH3 - C = C - CH3 is
methane is
| |
CH3 C2 H5 1)  CH 3 2 CH NH 2 2)  CH 3 3 N
1) 1,2 -diethyl butene
2) 2 - ethyl -3- methyl pentene 3)  CH 3  2 NH 4) CH 3 NH 2
3) 3 , 4 - dimethyl hex -3- ene
4) 2 , 3 - dimethyl pent -2- ene
30. Formula of phenyl carbinol and chloral are

respectively METAMERISM
1) C6 H 5CH 2CH 2OH and CHCl2CHO
36. The compound which is not isomeric with
2) C6 H 5CH 2OH and CCl3CHO diethyl ether is
3) C6 H 5OH and CH 2Cl.CHO 1) n-propyl methyl ether 2) 1-Butanol
3) 2-Methyl-2-propanol 4) Butanone
4) C6 H 5CHO and CHCl2CHO
31. The structure of isoprene is TAUTOMERISM
1) CH 3  CH  C  CH 2
37. Which of the following pairs of compounds are
CH 3 tautomers?
|
2) CH 2  C  CH  CH 2 1) Propanol & propanone
2) Ethanol & vinyl alcohol
CH 3 3) Ethanol & allyl alcohol
| 4) Vinyl alcohol & ethanal
3) HC  C  C  CH 2
KEY
CH 3
LEVEL - I
|
4) CH 2  C  CH 2  CH  CH 2 1) 2 2) 4 3) 1 4) 4 5) 4
6) 4 7) 2 8) 3 9) 1 10) 2
STRUCTURAL ISOMERISM 11) 4 12) 4 13) 1 14) 2 15) 4
16) 3 17) 4 18) 4 19) 2 20) 2
CHAIN ISOMERISM
21) 4 22) 4 23) 3 24) 2 25) 4
26) 1 27) 2 28) 3 29) 3 30) 2
32. Number of structural isomers for C4 H10O 31) 2 32) 2 33) 3 34) 3 35) 2
are 36) 4 37) 4
1) 6 2) 7 3) 4 4) 5
33. The simplest alkane capable of exhibiting
HINTS
chain isomerism has ___ carbon atoms
1) Three 2) Five 3) Four 4) Six
LEVEL - I
POSITION ISOMERISM
C C C
34. Which of the following alkanes can form only 3. 2
SP SP SP 2
two monochloro derivatives
1) Hexane 2) 2-Methyl pentane 11. Aromatic compounds contain  4n  2  e 
2) 2,3-Dimethyl butane 4) 3-Methyl pentane
O
FUNCTIONAL ISOMERISM 16 CONH2 group contain || and  NH 2
C 
group
35. Which of the following is the functional
isomer of methyl acetate? O
17. || group is present in R-CO-R, R-CHO,
1) Ethyl acetate 2) Propanoic acid
C 
3) Ethyl formate 4) Propanone
R-COOH
19. alkyl alkanoates are esters 4. Toluene has
CH 3  CN 1) 6 - and 3 - bonds
20. 2 |
2) 9 - and 3 - bonds
21. by rules
3) 9 - and 6 - bonds
1 2 3
C C  C C 4) 15 - and 3 - bonds
22.
| | 5. In which of the following compounds, carbon
C C2 H 5 uses SP 3 hybrid orbitals only for bonding?
4, 5
1) HCOOH 2) CH 3CHO
CH 2OH  CH 2OH 3)  C H 3 3 C O H 4)  N H 2  2 CO
23. 1 2
6. In which of the compound given below
C  C C  C contains more than one kind of hybridization
24. 4 3 2 1
(sp, sp 2 , sp3 ) for carbon
O
|| 1) C H 3 C H 2 C H 2 C H 3
25. CONH 2  CHO  C  OH
2) CH 3  CH  CH  CH 3
OH C
26. | | 3) CH2  CH  CH  CH2
C  C  C  C  CHO
5 4 3 2 1 4) H  C  C  H
7. The percentage of s- character of the hybrid
1 2 3 4 5
28. C  C C  C C orbitals in ethane, ethene and ethyne are
| respectively
CH 3
1) 50, 75, 100
29. CH 3  NH  CH 3 2) 10, 20, 40
30. C6 H 5CH 2OH is phenyl carbinol 3) 25, 33, 50
CCl3CHO is chloral 4) 25, 50, 75
LEVEL – II STRUCTURAL FORMULAE (OR)

CARBON SKELETON DIAGRAMS
STRUCTURE AND BONDING
1. The no. of  &  bonds present in C2 H 2 8. which of the following explains

respectively are
1) 1,2 2) 2, 1 3) 5, 2 4) 3, 2 this structure
2. The number of  electrons present in
CH 3
phenanthrecene |
1) 10 2) 14 3) 12 4) 16 1) 2) CH 3  CH 2  CH  NH 2
3. Which of the following statement is not

correct? CH3 CH 3
| |
1) Double bond is shorter than a single bond 3) NH 2  C  CH 2  CH 2 4) NH 2  C  NH 2
2) Sigma bond is weaker than  (Pi) bond | |
CH3 CH 3
3) Double bond is stronger than hydrogen bond
4) Covalent bond is stronger than hydrogen bond
16. The IUPAC name of the compound
NOMENCLATURE OF
CARBON COMPOUNDS is
9. Which of the following compounds does not 1) 3 - Chloro - 3 - phenyl - 1 - propene

have any tertiary hydrogen atoms 2) 3 - Benzyl - 3 -chloro - 1 - propene
1) (CH3)3CCH2CH3 3) 3 - phenyl - 3 - chloro - 1 - propane
2) (CH3)2CHCH2CH3 4) 3 - Chloro propene benzene
3) (CH3)2CHCH(CH3)2 17. The IUPAC name of the given structure
4) (CH3)3CH is
10. The functional group present in Anisole is 1) 1,2 -dimethyl cyclopropane
1) Ketone 2) Aldehyde 2) cyclopropane -1, 2 - dimethyl
3) Amine 4) Ether 3) 1 -methyl -1-methyl cyclopropane
11. The number & type of carbon atoms present 4) cyclopentane
in neopentane are 18. The IUPAC name of the given compound
1) four 10 carbons , one 40 carbon
2) two 10carbons , two 20 carbons or is
3) one 10 carbon , one 40 carbon 1) 2-methyl butane 2) 3-methyl butane
4) one 10 carbon , one 40 carbon 3) Pentane 4) Isopentane
CH 3 19. The IUPAC name of the given structure

12. The IUPAC name of CH  C|  CH  COOH
3
or is
is
1) 2 - Methyl - 2 - butenoic acid 1) 2,2 - Dimethyl butane 2) Isohexane
2) 3 - Methyl -3 - butenoic acid 3) 2,3 - Dimethyl butane 4) Di isohexane
3) 3 - Methyl - 2 - butenoic acid 20. The IUPAC name of the given compound
4) 2 - Methyl - 3 - butenoic acid
13. The IUPAC name of Cinnamaldehyde is is
1) 3 - Phenyl prop - 2 -enal
2) 1 - Phenyl - prop - 1 - enal 1) Octyl cyclopentane
3) 1 - Phenyl - prop - 2 - enal 2) 3- cyclopentyl octane
4) 3- Phenyl - prop - 1 - enal 3) Cyclopentane octane
14. The IUPAC name of the compound 4) 6- cyclopentyl octane
CH 3  CH  OH   COOH is 21. The IUPAC name of is

1) Lactic acid 1) but - 2 - ene - 2, 3- diol
2) 2 - Hydroxy propanoic acid 2) pent- 2 -ene -2, 3- diol
3) 3 - Hydroxy propanoic acid 3) 2 - methyl but- 2 - ene- 2,3-diol
4) Carboxy propanol 4) hex -2 - ene -2, 3 -diol
15. The IUPAC name of the compound 22. The IUPAC name of the compound
CH 3
|
CH 3  CH 2  CH  COOC2 H 5 is is
1) 2 - Ethyl - ethyl acetate
1) 2 - Methyl - 4 - hexanamine
2) Ethyl - 3 - methyl butanoate
2) 5- Methyl - 3 - hexanamine
3) Ethyl - 2 - methyl butanoate
3) 2 - Methyl - 4 - amino hexane
4) 2 - methyl butanoic acid
4) 5 - Methyl - 3 - amino hexane
WRITING THE STRUCTURE STRUCTURAL ISOMERISM

OF THE COMPOUND CHAIN ISOMERISM
WHOSE NAME IS GIVEN
26. Which isomer of C6 H14 has two isopropyl
23. The structure of 3-bromoprop-1-ene is groups
Br 1) 2-Methylpentane
|
2) 3-Methylpentane
1) CH 3  C  CH 2
3) 2,3-Dimethylbutane
2) CH 3  CH  CH  Br 4) 2,2-Dimethylbutane
3) CH 3  C  CH  Br
| POSITION ISOMERISM
Br
4) Br  CH 2  CH  CH 2 27. Number of dibromo derivatives possible for

24. Neo-heptyl alcohol is correctly represented propane are
as 1) 2 2) 3 3) 1 4) 4
CH 3 28. The number of aromatic isomers possible for
|
1) CH 3  C  CH  CH 2  CH 3 C7 H 8O is
| |
CH 3 OH 1) 2 2) 3 3) 4 4) 5
FUNCTIONAL ISOMERISM
CH 3
|
2) CH 3  C  CH 2  CH 2  CH 2  CH 3 29. Which of the following compounds is
|
OH isomeric with trimethyl amine?
1) 1-Propanamine 2) 2-Propanamine
CH 3 3) Both 1 and 2 4) 2-Butanamine
|
3) CH 3  C  CH 2  CH 2  CH 2  OH 30. Isomers of propanoic acid are
|
CH 3
1) HCOOC2 H 5 and CH 3COOCH 3
2) H  COOC2 H 5 and C3 H 7 COOH
C2 H 5 3) CH 3COOCH 3 and C3 H 7 OH
|
4) C2 H 5  C  OH 4) C3 H 7 OH and CH 3COCH 3
|
C2 H 5
METAMERISM
25. The structure of allylene is
1) CH 3  CH  CH 2 31. Which of the following compounds will show
2) CH 3  CH  CH  CH 3 metamerism?
1) CH 3  CO  C2 H 5
3) CH 3  CH 2  CH  CH 2
2) C2 H 5  S  C2 H 5
4) CH 3  C  CH
3) CH 3  O  CH 3
4) CH 3  O  C2 H 5

TAUTOMERISM
20.
32. The molecules

LEVEL - III
and are 1. The type of isomerism found in urea
1) Geometrical isomers 2) Tatutomers molecule is
3) Diastereomers 4) Metamers 1) Chain 2) Position
3) Tautomerism 4) Geometrical
KEY 2. A compound with molecular formula C4 H 4O
LEVEL - II has all the four carbon atoms and the oxygen
1) 4 2) 2 3) 4 4) 4 5) 3 atom in the ring. It also has two double
6) 2 7) 3 8) 1 9) 1 10) 4 bonds. The compound is
11) 1 12) 3 13) 1 14) 2 15) 3 1) Homocyclic and aromatic
16) 1 17) 1 18) 1 19) 3 20) 2 2) Heterocyclic and aromatic
21) 2 22) 2 23) 4 24) 3 25) 4 3) Homocyclic but not aromatic
26) 3 27) 4 28) 4 29) 3 30) 1 4) Heterocyclic but not aromatic

31) 2 32) 2 3. Which of the following sets contains only
carbocyclic compounds?
1) Thiophene, Oxirane, Pyrrolidine
HINTS 2) Piperidine, Cyclohexane, Benzene
3) Naphthalene, Cyclopropane , Bi-phenyl
LEVEL - II 4) Pyridine, Thiophene, Oxetane
4. IUPAC name of CH 3  CH  OCH 3   CH 2  NH 2
1. H  C  C  H contains 3 & 2 1) 2 - methoxy propanamine
2. Naphthalein has 5 bonds 2) 1- amino - 2- methoxy propane
7. %S character is Sp 3  Sp 2  Sp 3) 1- amino - 2- methyl - 2- methoxy ethane
4) 1- methoxy - 2- amino propane
8. ter. butyl amine
CH 2  CH  CH 2
C 5. IUPAC name of | | |
| CN CN CN
C C C
11. | 1) 3 - cyanopentane -1, 5- dinitrile
C 2) Propane -1,2,3 - tri nitrile
3) 1,2,3 - tri cyano propane
4) Propane - 1,2,3 - tricarbonitri le
17. 6. IUPAC name of
HOOC  CH 2  CH  CH 2  COOH
|
COOH
18.
1) 3 - Carboxylic pentane - 1, 5 - dioic acid
2) Propane - 1,2,3 - trioic acid
3) 1, 2, 3 - tricarboxylic propane
19. 4) Propane- 1,2,3 - tricarboxylic acid

7. Which of the following statement is 13. The IUPAC name of the following compound
incorrect?
1) - CH2 - contains secondary carbon atom
2) IUPAC names depend on structure is
3) Root word indicates number of carbon atoms
1) 1-Chloro -2, 4 - dinitro benzene
in the parent chain
2) 2 - Chloro -1, 4-dinitro benzene
4) Sum of numbers indicating position of
3) 1, 3 - Dinitro - 2 - chloro benzene
substituents must be minimum in IUPAC system.
4) 4 - Chloro -1, 3-dinitro benzene
8. The correct decreasing order of priority for
the functional groups of organic compounds
in the IUPAC system of nomenclature is
(AIEEE-2008) C 2 H 5  C  C H 2O H
||
1) -COOH,-SO3 H,-CONH2 ,-CHO
CH 2
2) -SO3 H,-COOH,-CONH 2 ,-CHO
1) 2 - Ethyl prop-2-en-1-ol
3) -CHO,-COOH,-SO3 H,-CONH2 2) 2- Hydroxymethyl butan-1-ol
4) -CONH 2 ,-CHO,-SO3 H,-COOH 3) 2- Methylene butan-1-ol
9. The IUPAC name of the following compound 4) 2- Ethyl - 3hydroxyprop-1-ene
15. The IUPAC name of
CH 3  C  CH 3  2  CH 2  CH  CH 2 is
CH 3 O
1) 2, 2- Dimethyl-4-pentene | || is
CH  CH  C  CH  C H 2O H
2) 4, 4- Dimethyl-1-pentene 3 2
3) 1, 1, 1-trimethyl-3-butene 1) 1- Hydroxy- 4-methyl-3-pentanone

4) 4, 4, 4-trimethyl-1-butene 2) 2-Methyl -5-hydroxy-3-pentanone
10. The IUPAC name of 3) 4-Methyl -3-oxo-1-pentanol
OH 4) Hexanol-1-one -3
|
CH 3  C  CH 2  C H  CH 3 16. The number of possible alkynes with
| | is
CH 3 CH 3 molecular formula C5 H 8 is
1) 2, 4 -Dimethyl pentanol -2 1) 2 2) 3 3) 4 4) 5
2) 2, 4 - Dimethyl pentanol -4 17. The number of possible open chain (acyclic)
3) 2, 2 - Dimethyl butanol - 2 isomeric compounds for molecular formula
4) Butanol -2 C5 H10 would be
11. The IUPAC name the compound
1) 8 2) 7 3) 6 4) 5
CH 3  CH  CH  CH 2
OH
| |
OH
|
OH is 18. What is the IUPAC name of the following
1) Butane - 2, 3, 4-triol Cl
2) Butane-1, 2, 3-triol
3) Pentane -1, 2, 3-triol
4) 2, 3- dihydroxy butanol
is
1) 3 - chloro cyclo hexa - 1, 5 - diene
(AIEEE-2004)
1) 3, 3- Dimethyl -1-cyclohexanol
3) 1 - chloro cyclo hexa - 2 , 5 - diene
2) 1, 1-Dimethyl -3- hydroxy cyclohexane
3) 3 , 3- Dimethyl -1- hydroxy cyclohexane
4) 1, 1-Dimethyl -3-cyclohexanol
19. What is the IUPAC name of the following 1) 3 - cyano - 2 - carboxy benzaldehyde
2) 2 - cyano - 6 - formyl benzaoic acid
3) 6 - cyano - 2 - formyl benzaoic acid
4) 2 - formyl - 6 - cyano benzaoic acid
23. What is the IUPAC name of the following
O CH 3
1) 1,2,3,4 - tetra ethyl cyclo butane

2) 1,1,2,4 - tetra ethyl - 3 - methyl cyclo butane
3) 3 - methyl -1,1,2,4 - 3 - tetraethyl cyclo butane
4) 1-sec butyl-2, 4 - diethy-3-methyl cyclo
butane O
1) 4 - acetyl cyclo hexanone
CHO
2) 4 - oxo - 1- acetyl cyclo hexane
HO
3) 4 - oxo - 1 - methanoyl cyclo hexane
4) 4 - methanoyl - cyclohexane
CH 2
1) 6 - hydroxy cyclohex - 2 - ene - 1 - al
2) 4 - hydroxy cyclohex - 1 - ene - 3 - al
3) 2 - hydroxy cyclohex - 5- ene - 1 - al
4) 1 - formyl cyclohex - 5 - ene - 2 - ol
Cl
Br 1) Ethenyl cyclo pentane

2) cyclopentyl ethene
3) cyclopentyl ethylene
4) vinyl cyclopentane
N O2
KEY
1) 1 - chloro - 2 - bromo - 4 - nitrobenzene
2) 1 - bromo - 2 - chloro - 4 - nitrobenzene LEVEL - III
3) 3 - bromo - 4 - chloro - nitrobenzene
4) 2 - bromo - 1 - chloro - 4 - nitrobenzene 1) 3 2) 2 3) 3 4) 1 5) 4
22. What is the IUPAC name of the following 6) 2 7) 2 8) 1 9) 2 10) 1
COOH 11) 2 12) 1 13) 1 14) 1 15) 1
OHC 16) 2 17) 3 18) 2 19) 2 20) 1
CN
21) 4 22) 2 23) 1 24) 2

4. How many sigma and Pi bonds are present
HINTS
in the following molecule
LEVEL - III HC  C  CH  CH  CH 3
1) sigma C-C bonds =4, sigma C-H bonds = 6,
pi C-C bonds = 3
3 2 1
C  C  CH 2  NH 2 2) sigma C-C bonds =5, sigma C-H bonds = 4,
4. | pi C-C bonds = 2
OCH 3 3) sigma C-C bonds =4, sigma C-H bonds = 2,
5. Like functional group like rule pi C-C bonds = 5
6. Like functional group like rule 4) sigma C-C bonds =4, sigma C-H bonds = 4,
pi C-C bonds = 4
6 5 4 3 2 1
5. How many sigma and pi bonds are present
C  C  C  C  C2 H 5
9. | | in the following molecule
CH 3 C2 H 5 CH 2  C  CH  CH 3
13 1) sigma C-C bonds =5, sigma C-H bonds = 5,
C2 H 5  C  CH 2OH pi C-C bonds = 4
|| 2) sigma C-C bonds =3, sigma C-H bonds = 6,
14. CH 2 pi C-C bonds = 2

3) sigma C-C bonds =4, sigma C-H bonds = 5,
O pi C-C bonds = 2
||
15. C  C  C  C  CH 2OH 4) sigma C-C bonds =4, sigma C-H bonds = 6,
5 4 3 2 1 pi C-C bonds = 4
LEVEL - IV MCQ’S WITH MORE THAN ONE

ANSWER
1. The hybridisation of carbon atoms in C  C
single bond is HC  C  CH  CH 2 is 6. Compounds having equal no of hybrid
orbitals among the following are
1) Sp3  Sp3 2) Sp 2  Sp3
1) 2)
3) Sp  Sp 2 4) Sp 3  Sp
3) 4)
2. Which of the following order regarding the
size of hybrid orbital of carbon is correct? 7. The following is a structure of
2 3 2 3
1) Sp  Sp  Sp 2) Sp  Sp  Sp 1) diethyl ether 2) dimethyl ether
3) Sp  Sp 2  Sp 3 4) Sp  Sp 2  Sp 3 3) ethoxy ethane 4) ethoxy methane
3. Which of the following orders regarding the 8. The corect statements about C6 H5 COCl is
electronegativity of hybrid orbital of carbon 1) The IUPAC name of the compound is
is correct? Benzene carbonyl chloride
1) Sp  Sp 2  Sp 3 2) Sp  Sp 2  Sp 3 2) The IUPAC name of the compound is Benzoyl
chloride
3) Sp  Sp 2  Sp 3 4) Sp  Sp 2  Sp 3
3) It’s an aromatic compound
4) It’s an aliphatic compound
9. The correct IUPAC name of the compound 18. Tautomerism is shown by
CH 2 -COOH 1) R-C  N 2) R-NO 2
| is
CH 2 -COOH 3) R-CHO 4) R-COOH
1) 1,4-Butane dioicacid 19. Which are functional isomers?
2) Ethane-1,2-dicarboxylic acid 1) Butan-2-ol and Ethoxy ethane
3) Succinic acid 2) Ethanal and vinyl alcohol
4) 1,2-Ethane dioic acid
3) Acetaldehyde and acetone
10. Correct statements about CH3 -CH 2 -CN is
4) Ethanoic acid and methyl formate
1) common name of the compound is ethyl
20. Only two isomeric monochloro derivatives
cyanide
are possible for:
2) IUPAC name of the compound propane-1-
1) n-Butane
nitrile
3) secondary suffix of the compound is nitrile 2) 2,4-Dimethyl pentane
4) IUPAC name of the compound is ethane nitrile 3) Benzene
11. Which of the following are heterocyclic 4) 2-Methyl propane
aromatic compounds? 21. Which of the following is (are) having Sp 2
hybridisation
1) 2)
1) Benzene 2) Ethane
3) Ethyne 4) Ethene
3) 4) 22. The structure represents
12. Carbocyclic compounds among the following 1) Propane oxide 2) Oxirane
1) cyclohexane 2) naphthalene 3) Epoxide 4) ethylene oxide
3) pyrrole 4) cyclopropene
13. Which of the following is (are) unsaturated 23. The structure has
compounds?
1) Three Sp3 carbon atoms
1) Benzene 2) Hexane
3) cyclohexene 4) Propene 2) two Sp 2 carbon atoms
14. Which is isomer of diethyl ether? 3) two Sp carbon atoms
1) Methyl-n-propyl ether
4) eight Sp3 -S sigma bonds
2) Butan-1-ol
3) Butan-2-ol 4) MATRIX MATCH TYPE

15. Which cannot show tautomerism?
24. What is the type of Hybridisation of each
1) 2) carbon in the following compounds?
a) CH 3Cl p) sp 2
3) CCl3 -CHO 4)
16. Metamerism is shown by b) (CH 3 ) 2 CO q) sp3 , sp 2 , sp 2 , sp
1) Diethylether 2) Diethylketone c) CH 3CN r) sp 3
3) Diethylamine 4) Dimethylether
17. C4 H10 O can exhibit d) HCONH 2 s) sp 3 , sp
1) Positional isomerism 2) Chain isomerism e) CH 3CH  CHCN t) sp 3 , sp 2
3) Optical isomerism 4) Functional isomerism
25. MATRIX MATCH Answer the following questions based on the
SET-I SET-II above paragraph
a) Benzene p) dihydric alcohol 29. How many Sp 2 -Sp2 bonds are between the
b) Pyridine q) heterocyclic carbons in above structure
c) Alkylcyanide r) aromatic
1) 3 2) 4 3) 1 4) 2
d) Glycol s) alkane nitrile
30. The bond line diagram of the given compound
t) carbocyclic
is
26. MATRIX MATCH
SET-I SET-II
a) n-Butane p) Carbocyclic 1) 2)
b) Pyrrole q) Aromatic
c) Naphthalene r) Heterocylic
d) 30 -Butyl alcohol s) Bicylic
t) Saturated 3) 4)
27. MATRIX MATCH
SET-I SET-II 31. How many pure orbitals are present in the
a) Alkanes p) Cn H 2n-2 above compound?
b) Alkynes q) Cn H 2n+2 1) 9 2) 10 3) 14 4) 12
c) Alcohols r) Saturated 32. The ratio between the pure and hybrid
hydrocarbons orbitals is?

1) 7:10 2) 8:7 3) 5:9 4) 1:2
d) Ethers s) Sp3 hybridized
oxygen atom 33. The ratio between the Sp 2 carbons and
t) Secondary suffix Sp 3 carbon atoms is ?
is - al 1) 2:1 2) 1:2 3) 1:4 4) 4:1
28. MATRIX MATCH
SET-I
COMPREHENSION
a) Cyclic and saturated
b) Cyclic and unsaturated The conversion of a keto form into enol is
c) Aromatic and carbocyclic enolisation. It depends on structural factor,
d) Aromatic and heterocyclic temperature and nature of solvent. Resonance
SET-II and hydrogen bonding increases enol content.
p) Cyclo propene, Cyclobutene Enolic form of phenol is more stable than keto
q) Benzene, Naphthalene, Anthracene form by -13 kcal/mole of energy hence phenol
r) Pyridine, Pyrrole, Furan exist exclusively as an enol. Enolic tautomer is
s) Cyclopentane, Cyclohexane less polar due to intramolecular hydrogen bonds
than the corresponding keto form. Any polar
COMPREHENSION
solvent would decrease the enolisation and favour
In the Analysis of an organic compound, it was
keto form intramolecular hydrogen bonding
found that. It contains 7 carbon atoms, there
stablized enol form by 7kcal/mole and resonance
are two C = C bonds and one C  C bond. This
stabilizes enol form by 15 kcal/mole.
compound is a hydrocarbon. Hydrocarbons have
34. The enol content of ethyl acetoacetate is
only carbon and hydrogen elements.
maximum in
On structural analysis it was found that it is
covalent in nature and expected structure is 1) water 2) acetic acid
3) ethanol 4) hexane

35. Which one of the following compounds has

maximum enol content
1) CH3 COCH 2 COOCH 3
2) CH 3COCH 2 COOC2 H 5
3) CH 3COCH 2 COCH 3
4) C6 H5 COCH 2 COC6 H 5
36. Ketonic form predominates in
1) CH3 COCH3
2) C6 H 5 COCH 2 COCH3
3) CH 3COCH 2 COCH 3
4) CH 3COCH 2 COOC2 H 5
KEY
LEVEL - IV
1) 3 2) 2 3) 1 4) 1
5) 2 6)1,3 7) 1,3 8) 1
9) 1,2 10) 1,2,3 11) 2,3,4
12) 1,2,4 13) 1,3,4

14) 1,2,3 15) 1,2,3
16) 1,2,3 17) 1,2,4
18) 2,3 19) 1,2,4
20) 1,4 21) 1,4
22) 2,3,4 23) 1,2,4
MATRIXMATCHTYPE
24) a-r, b-t, c-s, d-p, e-q

25) a-r,t; b-q,r ;c-s; d-p
26) a-t, b-q,r c-q,s d-t
27) a-q,r b-p, c-s, d-s
28) a-s, b-p,q c-q, d-r
COMPREHENSION
29) 4 30) 2 31) 3

32) 1 33) 4 34) 4
35) 4 36) 1

02-Basic Principles of Organic Srinu - CW

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JEE MAINS - VOL - IV ORGANIC CHEMISTRY - SOME BASIC PRINCIPLES & TECHNIQUES

ORGANIC CHEMISTRY - SOME BASIC

NISHITH Multimedia India (Pvt.) Ltd., 27

 sp3 carbon is called saturated carbon.

28 NISHITH Multimedia India (Pvt.) Ltd.,

 Determination of bond pairs : Number of bp =

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structural representation of organic Examples of bond line structures

5. The various ways of representing 2 - bromo

6. In cyclic compounds, the bond - line formulas

NISHITH Multimedia India (Pvt.) Ltd., 31

Acyclic or Open Cyclic or Closed chain

Saturated Un saturated Homocyclic or Heterocyclic

Alicyclic Aromatic Aromatic Non- Aromatic

b) Aromatic compounds. (b) Aromatic heterocyclic compunds :

NISHITH Multimedia India (Pvt.) Ltd., 33

Note : The generic word for a carbon chain is alk

Unsaturated Alk -ene Alkene (eg : ethene)

- C  C- Alk -yne Alkyne

34 NISHITH Multimedia India (Pvt.) Ltd.,

Total number of 1° hydrogen atoms : 15

Common and IUPAC names of alkyl groups

36 NISHITH Multimedia India (Pvt.) Ltd.,

 CH 3  CH  CH 2  OH Sec - butyl alcohol 2- Butanol

 CH 3  C  OH t - butyl alcohol 2 - Methyl - 2- Propanol

Formula Common Name IUPAC name

NISHITH Multimedia India (Pvt.) Ltd., 39

4 Bromo + Cyclo + Hex + an(e)* + 1-one = 4 - Bromocyclohexan - 1 - one or 4-

wrong selection (Longest chain of 7C atom with two branches)

II. Lowest number or lowest sum rule.

CH3 CH2 - CH3

NISHITH Multimedia India (Pvt.) Ltd., 41

42 NISHITH Multimedia India (Pvt.) Ltd.,

7 HC  C - CH2 OH 19 CH3 -CH2 -O -CH2 - CH2 Cl

44 NISHITH Multimedia India (Pvt.) Ltd.,

Nomenclature of Bicyclo Compounds: of the compound with the principal funcitonal

square brackets containing the arabic numerals

1-chloro-4-nitro Benzene Benzene

Nomenclature of Aromatic Compounds:

4-ethyl - 2 - fluroanisole. 2-phenylethanol

46 NISHITH Multimedia India (Pvt.) Ltd.,

Structural isomerism 1- Butene 2- Butene

C9 H 20 35 CH3-CH2 -CHO & C H 3  C  CH 3

phenyl methanol 2-methyl phenol

 Hydrocyanic acid is an example of dyad system

NISHITH Multimedia India (Pvt.) Ltd., 49

CH 3  C  CH 2  C  OC2 H 5  keto form 92%  OH

 Analysing the acidity of hydrogen atom of active atom.

1) Functional isomers 6) 1 7) 3 8) 2 9) 1 10) 4

STRUCTURE AND BONDING 1)

1. Which hybrid orbitals are involved in the

3) sp and sp2 4) only sp3 CH 2

30. Formula of phenyl carbinol and chloral are

LEVEL – II STRUCTURAL FORMULAE (OR)

1. The no. of  &  bonds present in C2 H 2 8. which of the following explains

3. Which of the following statement is not

9. Which of the following compounds does not 1) 3 - Chloro - 3 - phenyl - 1 - propene

CH 3 19. The IUPAC name of the given structure

CH 3  CH  OH   COOH is 21. The IUPAC name of is

WRITING THE STRUCTURE STRUCTURAL ISOMERISM

4) Br  CH 2  CH  CH 2 27. Number of dibromo derivatives possible for

58 NISHITH Multimedia India (Pvt.) Ltd.,