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Organic Chemistry Basics

Introduction and classification :
1. Based on their source, chemical compounds are classified into 3 types by Lemery:
i) Mineral source ii) Vegetable source iii) Animal source
Vital force theory :
Lavoiser found that the compounds from vegetable and animal sources contain similar
composition.
Then Berzelius classified the above 3 types into 2 types and he coined the new terms Organic and
Inorganic.
i) Organic compounds: These are present in living beings (plants, animals etc.)
ii) Inorganic compounds: These are present in minerals
But now based on the structure and chemical behaviour, the compounds are classified as
i) Organic compounds ii) Inorganic compounds
Organic compounds are carbon compounds and the study of chemistry of carbon compounds is
called organic chemistry.
Organic compounds contain Carbon, Hydrogen, essentially and Oxygen, Nitrogen, Sulphur,
Phosphorus, Halogen etc frequently.
Father of organic chemistry is Wohler who synthesized the first organic compound in laboratory
from inorganic substances.
KCl
NH4Cl+KCNO
NH4CNO NH2 C NH2
ammonium cyanate ||
O
With the synthesis of urea vital force theory of Berzelius was discarded, according to which
organic compounds cannot be synthesized without any vital force.
Kolbe synthesised CH3COOH from its elements.
Berthelot synthesised CH4
Carbon is tetravalent as it contains four unpaired electrons in its excited state configuration. The
tetravalency of carbon was given by Vanthoff and Lebel who were awarded the first nobel prize in
chemistry.
Ground state configuration of 'C' : 6 C 1s2 2s2 2p1x 2p1y 2poz
Excited state configuration of 'C' : 6 C 1s2 2s12p1x 2p1y 2p1z
Carbon alone forms about 10 millions of organic compounds where as the remaining elements together
could form just about 50000 compounds.
Largest number of compounds formed by carbon because of its marked features.
1) Highest catenation
2) Tetravalency
3) Ease of formation of multiple bonds
Natural sources of organic compounds are coal, petroleum, natural gas, animals and plants.

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 Organic Chemistry
Classification of organic compounds :
Classification based on carbon chain :

Open chain Closed chain

(Aliphatic or Acylic) (Ring or cylic )

Unsaturated Homocylic Heterocyclic

Saturated
(Carbocyclic )
Ex. Alkanes Ex. Alkenes, Ex. Furan,
Alkynes Pyrrole,
Pyridine,
Alicyclic Aromatic Thiophene
Ex. Cycloalkanes Ex. Benzene

Carbon compounds are classified into various types based on the nature of functional
groups:
Functional Name of the functional
Name Formula
group group
1) Alkanes (paraffins) RH CC Single bond
2) Alkenes (olefins) RCH =CH2 > C = C< Double bond
3) Alkynes (acetylenes) R C CH C C Triple bond
4) Alkyl halides
RX X Halogen
(Haloalkanes)
5) Alcohols
R OH OH Hydroxy
(Alkanols)
6) Ethers R OR O Ether
7) Amines (Amino alkanes) R NH2 NH2 Amino
8) Aldehydes
R CHO CHO Aldehyde
(Alkanals)
9) Ketones (Alkanones) R CO R >C=O Keto
10) Carboxylic
R COOH COOH Carboxyl
acids(Alkanonic acids)
11) Esters (Alkyl
R COOR COOR Ester
alkanoates
12) Amides R CONH2 CONH2 Amide
13) Cyanides R CN CN Cyanide
14) Nitro compounds R NO2 NO2 Nitro
15) Sulphonic acids R SO3H SO3 H Sulphonic Acid

Open chain compounds: Carbon atoms are linked to one another to form straight chains or
branched ones but not rings.
Open chain compounds are also called aliphatic compounds. Ex: Alkanes, alkenes, alkynes and
their derivatives.
Cyclic compounds: Carbon atoms are linked to one another to form ring.
Based on the number of rings, they may be monocyclic or polycyclic.
Homocyclic: Ring is formed by carbon atoms only. Ex: Benzene, Phenol, Toluene, Cyclopropane
etc.

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 Organic Chemistry
Heterocyclic: Along with carbons some hetero atom like, N, O, S, P, etc is involved in forming the
ring.

N
O N
S
Furan Thiophen H Pyridene
Pyrrole
Alicyclic: These are cyclic compounds but resemble open chain compounds in properties.
Ex.: Cycloalkanes, cycloalkenes, cycloalkynes
Aromatic: The ring compounds which resemble benzene in structure and properties are called
aromatic compounds.
These may be homocyclic or heterocyclic.
Ex.:
OH

Benzene Phenol Napthalene

O S

Furan Thiophene
Bonding in carbon compounds :
In all its compounds, carbon undergoes only
3 types of hybridisation i.e. sp, sp2 and sp3.
The tetravalency of carbon is possible in its excited state configuration, as it contains four
unpaired electrons
The energy required for the promotion of electron from 2s orbital to 2p orbital is 501.6 kJ/mol.
sp3 hybridisation is found in alkanes. sp3 hybrid carbon forms four single bonds or four sigma
bonds. The ratio of s character to p character in each sp3 hybrid orbital is 1 : 4. sp3 hybrid
carbon forms C C and C H bonds. Shape of the molecule is tetrahedral and bond angle is
109.
sp2 hybridisation is found in alkenes. sp2 hybrid carbon forms 3 sigma bonds and 1pi bond or
one double bond and two sigma bonds. The ratio of s character to p character in sp2 hybrid
orbital is
1 : 2. Shape of molecule is trigonal planar and bond angle is 120.
sp hybridisation is found in alkynes and cumulative dienes. SP hybrid carbons forms 2 and 2
bonds i.e. 1 triple and 1 single or 2 double bonds.
The ratio of s character to p character in sp hybrid orbital is 1 : 1.
Shape of molecule is linear and bond angle is 180.

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 Organic Chemistry
3. STRUCTURAL FORMULAE (OR) CARBON SKELETON DIAGRAMS

1. In bond line diagrams the atoms other than C & H are only shown. Hydrogen atoms if they are
bonded to Hetero atoms like N & O are shown.

2. CH 3 CH 2 CH 2 CH 3
Butane

CH 3 CH 2 CH 2 CH 2 NH 2
Butanamine

3.
Cyclo propane

Cyclo propane

Cyclo butane

5.

Chloro cyclo pentane

6.

7.

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 Organic Chemistry

8.

4.METHODS OF PURIFICATION OF ORGANIC COMPOUNDS

Methods of purification of organic Compounds:
Organic compounds obtained either from natural sources or synthetic processes in the laboratories
are contaminated with impurities. These are purified by different methods.
I. Methods of purification of solids:
1.Crystallisation:-
This method is useful to purify the solid organic compounds.
The principle involved in this method is that the compound should be insoluble at low
temperature but soluble at higher temperatures in the given solvent. Impurities are either insoluble
or soluble and go into filtrate.
The insoluble impurities are removed by filteration in hot condition.
The crystals of the compound are seperated by filtering under reduced pressure using Buckner
funnel.
Repeated crystallisation is required and the coloured impurities are removed by adsorbing them
with activated charcoal.

2. Sublimation : -
It is used to purify activated solid organic compounds which undergoes sublimation.
If the compound is sublimating the impurity should not sublimate.
If the compound to be purified has high vapour pressure below its melting point and sublimates
readily on heating and the impurities dont sublimate.
The pure compound is seperated by scratching the watch glass.
If the sublimating substances have a low vapour pressure or decompose on heating before
sublimation, then the sublimation is carried out under low pressure.

II. Methods of purification of liquids:-

1.Simple distillation:- The vapourisation of a liquid by heating and subsequent condensation of
vapours by cooling is known as distillation.
This process is useful for purification of liquids contaminated with non volatile impurities.
The liquids that have boiling point difference greater than 400 C can be purified by this method.

2.Fractional distillation:-
This process is useful for the purification of liquids having boiling point difference less than 400C.
In this process, liquid with high b.p. is collected in the condenser and liquid with low b.p. is
collected in the receiver.
3.Distillation under reduced pressure:-
This method is useful to purify liquids that have very high boiling points and those which
decompose at or below their boiling points.
At reduced pressure the boiling point of a liquid is also reduced. Hence its decomposition is
prevented.

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 Organic Chemistry

4. Steam distillation:-
The liquids insoluble in water possess high boiling point and steam volatile and the impurities are
not steam volatile are purified by this method.
Principle in steam distillation is - sum of the vapour pressure of organic liquid (P1) and that of
water (P2) is equal to atmospheric pressure (P) and mixture boils.
The water layer and the organic liquid layer are seperated using separating funnel.
Ex:- Aniline is purified by this method from Aniline - water mixture
Relative masses obtained in steam distillation process is calculated by a formula =
WA nA M A p A0 M A
= = ; Where WA and WB are the masses of A and B
WB nB M B p 0B M B
M A and M B are the molecular masses of A and B
PA0 and PB0 are the vapour pressures of A and B
At 98.50 C water and aniline have vapour pressures 717 torr and 43 torr. In steam distallation at
WH 2O 717 18
98.50 C , the relative masses obtained are = = 3.23
WAniline 43 93
5. Solvent extraction( differential extraction) :-
In this method, organic compound is separated from its aqueous solution by using its solubility
which is different with organic solvent and water.
6. Chromatography:-
It was discoverd by Tswett in (1906). He separated chlorophyll and Xanthophyll and other
compounds by using adsorbent CaCO3 .
It is classified into three types based on the physical states of stationary phase and mobile phase.
Chromatography involves the three steps
a) Adsorption and retention of a mixture of substances on the stationary phase and separation of
adsorbed substances by the mobile phase to different distance on the stationary phase.
b) Recovery of the substances separated by a continuous flow of the mobile phase (known as
elution)
c) Qualitative and quantitative analysis of the eluted substances

S.No. Chromatography Process Stationary Phase Mobile Phase

1. Column chromatography (Adsorption) Solid Liquid

Liquid liquid partition

2. Liquid Liquid
chromatography

3. Paper chromatography Liquid Liquid

4. Thin layer chromatography (TLC) Liquid (or) solid Liquid

5. Gas liquid chromatography (GLC) Liquid Gas

6. Gas solid chromatography (GSC) Solid Gas

7. Ionic change chromatography Solid Liquid

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 Organic Chemistry

Important chromatography techniques are

1) Adsorption chromatography : a) Column chromatography, b) Thin layer chromatography
2) Partition chromatography : a) Paper chromatography
a) Column Chromatography
The principle used in this method is differential adsorption.
In the column chromatography the components of a mixture are separated by a column of
adsorbent (stationary phase) packed in a glass tube.
The mixture to be adsorbed on the adsorbent is placed at the top of the stationary phase.
A suitable eluant, either a single solvent or a mixture of solvents is allowed to flow down the
column slowly.
The most readily adsorbed substances are retained near the top and others come down
accordingly to various distances.
b)Thin layer chromatography (TLC):
This also based on the adsorption differences.
The glass plate which is coated with adsorbent (Eg : Silica gel, alumina) as a thin layer (0.2mm
thick) is called TLC plate or chromoplate.
The plate is then kept in a closed jar containing the eluant.
The relative adsorption of a component of the mixture is expressed in terms of RETARDATION
FACTOR (Rf) value.
Distance moved by the substance from base line (X)
Rf =
Distance moved by the solvent from base line (Y)
The colourless compounds which fluorescence are detected with ultraviolet light.
Spots of compounds are even detected by allowing them to adsorb iodine, when they give brown
spots.
Some times an appropriate reagent is sprayed, as ninhydrin solution to detect aminoacids.
c) Partition Chromatography
This is based on continuous differential partitioning of components of a mixture between the
stationary phase and the mobile phase.
In paper chromatography, a special paper called chromatography paper contains water trapped in
it which acts as the stationary phase.
The chromatography paper spotted with the solution of the mixture at the base is suspended in a
suitable solvent or a mixture of solvents. This solvent (s) acts as the mobile phase.
The solvent rises up the paper by capillary action and moves over the spot.
The paper selectively retains different components as per their differing partition in mobile and
stationary phases and is known as chromatogram.
The spots of the separated coloured compounds are detected.

5. QUALITATIVE ANALYSIS OF ORGANIC COMPOUNDS

Qualitative analysis of organic compounds
1) Detection of carbon and hydrogen
Carbon and hydrogen are detected with - CuO (Cupric Oxide)
If carbon is present, its forms CO2 gas. The CO2 gas turns lime water milky
C + 2CuO 2Cu + CO2
Ca ( OH)2 + CO2 CaCO3

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 Organic Chemistry
If hydrogen is present in the compound it forms H2O vapour. H2O vapours when passed over
white anhydrous CuSO4 turns it blue by forming CuSO45H2O.
2H + CuO Cu + H2O
CuSO 4 + 5H2 O CuSO4 5H2 O
( white ) (blue )

2) Detection of halogen, nitrogen and sulphur ( Lassaignes test or sodium extract test)
In Lassaignes test, the compound is heated strongly in an ignition tube to fuse with sodium metal.
Here nitrogen present in the organic compound is converted as .CN
Na + C + N NaCN
from organic compound sodium cyanide
If sulphur is present in the organic compound is converted as S 2
2Na + S Na2 S
sodium sulphide
If halogens are present in the organic compound are converted as X
2Na + X 2 2NaX(X = Cl, Br, I)
The above obtained fused mass is extracted with water by plunging the red hot ignition tube in
distilled water and the contents are boiled for 10 minutes and filtered. The filtrate is called
sodium extract.
i) Test for nitrogen:
Take a portion of the sodium extract, if it is not alkaline add NaOH solution to it and then freshly
prepared ferrous sulphate solution.
Now add 2 or 3 drops of FeCl3 solution, cool, acidify with conc HCl.
A prussian blue or green precipitate (or) coloration is observed if nitrogen is present.
FeSO4 + 2 NaOH Fe ( OH )2 + Na2 SO4
6 NaCN + Fe ( OH )2 Na4 Fe ( CN )6 + 2 NaOH
sodium ferrocyanide
3 Na4 Fe ( CN )6 + 4 FeCl3 Fe4 Fe ( CN )6 + 12 NaCl
3
Ferric ferrocyanide (prussian blue)

ii) Test for sulphur :

To a portion of the Na extract add freshly prepared sodium nitroprusside solution.
A deep violet colouration takes place.
2 4
S 2 + Fe ( CN )5 NO Fe ( CN )5 NOS
nitroprusside violet
If N,S both are present gives thiocyanate, Na + C + N + S NaSCN
thiocyanate
3
To this if FeCl3 solution is added, Fe3+ + SCN Fe ( SCN )6 .
It gives only blood red colour.
No Blood red colour or prussian blue colour indicates that there are no N or S. If sodium fusion is
carried out with excess of Na the thiocyanate decomposes to yield CN and S2.
Na SCN + 2 Na NaCN + Na2 S

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 Organic Chemistry
Sodium fusion extract is acidified with acetic acid and then lead acetate solution is added
Pb 2 + S 2 PbS
black ppt
iii) Tests for halogens: The sodium fusion extract is acidified with nitric acid. Now it is treated
with AgNO3 solution. Ag + + X AgX
If white precipitate is formed that is soluble NH 4OH in solution, the halide is Cl . Hence
chlorine is present.
If pale yellow precipitate, sparingly soluble NH 4OH in solution is formed it is bromide ( Br )
and the halogen is bromine.
If an yellow precipitate, almost insoluble in NH 4OH solution is formed it is ( I ) iodide and the
halogen is iodide.
c) Detection of phosphorus:
The compound is heated with an oxidising agent say sodium peroxide. The P in the organic
3
compound is oxidised to PO4 . The solution is boiled with HNO3 and treated with ammonium
molybdate.
A canary yellow precipitate formation indicates the presence of phosphorous in the compound.
. Na3 PO4 + 3HNO3 H 3 PO4 + 3 NaNO3
H 3 PO4 + 12 ( NH 4 )2 MoO4 + 21 HNO3 ( NH 4 )3 PO4 .12 MoO3 + 12 H 2O
ammonium phosphomolybdate

d) Detection of oxygen:
There is no direct test for oxygen.
The organic compound when heated in pure nitrogen atmosphere if water droplets are formed on
the walls of the test tube oxygen is detected.
Otherwise after determining the % composition of all elements in the compounds if it does not
come to 100%, the remaining is of oxygen.
Even by detecting functional groups like OH , CHO, COOH , NO etc oxygen is detected.

6. QUANTITATIVE ORGANIC ANALYSIS

Quantitative Organic Analysis

1. Estimation of Carbon and hydrogen:- (Leibig method)
A known weight of the organic substance is taken and completely burnt in excess of air &
Copper (II) oxide. Carbon changes to CO2 and hydrogen changes to H2O as follows.
y y
CxHy + x + O2 xCO2 + H2 O
4 2
The CO2 and H2O obtained are passed through weighed U tubes Containing anhydrous CaCl2
and caustic potash respectively. The increased weight of these two tubes give the weight of H2O
formed and weight of CO2 formed.
12 Wt.of CO2 formed
% of C = 100
44 Wt. of Organic compound
2 Wt.of H2 O formed
% of H= 100
18 Wt. of Organic compound

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 Organic Chemistry
After calculating the percentage composition all C and H in the compound if their sum is not
100, then the difference is assumed as oxygen.
2. Estimation of Nitrogen:
There are two methods to estimate nitrogen in the given compound. They are
i. Dumas method ii. Kjeldahls method

i. Dumas method:-
In this method a known weight of organic compound is heated strongly with dry curpic oxide.
Carbon and hydrogen get oxidised to carbondioxide and water vapour. Nitrogen if present is
converted to N2 is collected over KOH solution and its volume is determined at S.T.P
y y z y
CxHyNz + 2x + CuO xCO2 + H2O + N2 + 2x + Cu
2 2 2 2
28 Volume of Nitrogen at S.T.P
% of N = 100
22400 Weight of organic compound
ii. Kjeldahls method:-
In this method the given organic compound is treated with Conc.H2SO4 in the presence of small
amounts of CuSO4 to convert nitrogen into ammonium sulphate. Then ammonium sulphate is
treated with excess of NaOH to liberate NH3 gas.
The ammonia evolved is neutralised with excess of Conc H2SO4. which is relatively more in
amount than that is required to neutralise NH3 gas. Now, the excess of acid is titrated with
standard alkali solution. From this the amount of H2SO4 used to neutralise NH3 formed is
calculated and from that
percentage of nitrogen is calculated.

Oraganic compounds + H2SO4 (NH4 )2 SO4

(NH4 )2 SO4 + 2NaOH Na2SO4 + 2H2O + 2NH3
2NH3 + H2SO4 (NH4 )2 SO4
1.4 N V
% of N =
Wt.of organic compound
Where N = Normality of acid
V = Volume of acid (ml) neutralised by ammonia
3. Estimation of halogens (Carius method)
In this method a known weight of organic compound is heated with fuming nitric acid in the
presence of Ag NO3 in a hard glass tube called Carius tube.
Carbon and hydrogen of the compound are oxidised to CO2 and H2O. Halogen forms Silver
halide (AgX). It is filtered, washed dried & weighed.
At.wt of X Wt.of Ag X
% of Halogen ( X ) = 100
Mol.wt of AgX Wt of Oraganic compound
35.5 Wt.of AgCl formed
% of Cl = 100
143.5 Wt of Oraganic compound
80 Wt.of AgBr formed
% of Br = 100
188 Wt of Oraganic compound
127 Wt.of Ag I formed
% of I = 100
235 Wt of Oraganic compounds

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 Organic Chemistry

4. Estimation of sulphur:-
A known weight of organic compound containing sulphur is heated with Na2O2 or fuming HNO3
in a carius tube. The sulphur in it is oxidised to H2SO4. The acid is precipitated as BaSO4 by
adding excess of BaCl2 solution. The precipitate is filtered, washed, dried and weighed.
32 Wt. of BaSO 4
% of S = 100
233 Wt.of Oraganic compound

5. Estimation of Phosphorus:
To estimate phosphorus in the given organic compound, a known mass of organic compound is
heated with fuming nitric acid in a Carius tube. Phosphorus is oxidised to phosphoric acid. The
acid is precipitated as ammonium phosphomolybdate ( NH 4 )3 PO4 .12MoO3 by adding ammonia
and ammonium molybdate solutions.
Sometimes, the acid is precipitated by adding magnesia mixture.
Magnesia mixture is obtained by dissolving 100.0g. of MgCl2. 6 H2O and 100.0g.of NH4Cl in
water, then adding 50.0 ml of conc.NH4OH and diluting the solution to 1000 ml.
A Precipitate of magnesium ammonium phosphate ( Mg NH 4 PO4 ) is formed which on ignition
gives magnesium pyrophosphate (Mg2P2O7).
2 31 Wt. of Mg 2 P2 O7
% of P = 100 (or)
222 Wt.of Oraganic compound
31 Wt. of ( NH 4 )3 PO 4 .12MoO3
% of P = 100
1877 Wt.of Oraganic compound

6. Estimation of Oxygen:
The percentage of oxygen in an organic compound is found indirectly by the difference between
100 and total percentage of other elements.
In the direct method, a known mass of organic compound is decomposed by heating in a stream
of nitrogen gas. The mixture of gaseous product containing oxygen is passed over red hot coke to
convert all oxygen in those oxides to CO. Then the mixture is passed through warm iodine
pentoxide ( I2 O5 ) to convert CO to CO2 and liberating iodine.
Compound Heat
N2
O2 + other gaseous products ;
2C + O2
1373 K
2CO ; I 2O5 + 5CO I 2 + 5CO2
Homologous series :
The series of organic compounds having a common difference of CH2 between any two
successive members is called homologous series.
The classification and study of the members of the homologous series is called homology and the
members of the series are called homologues.
Characteristic features of homologous series :
i) There is a common difference of CH2 between two successive members. There is a common
difference of 14 in molecular weight between two successive members.
ii) They possess similar chemical properties.
iii) There is regular gradation in their physical properties
iv) They can be prepared by similar methods.
v) They can be represented by a general molecular formula.

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 Organic Chemistry
Ex. Alkanes CnH2n + 2
Alkenes CnH2n
Alkynes Cn H2n 2
Alkyl halides CnH2n+1 X
Alcohols and ethers CnH2n+2O
Aldehydes and ketones CnH2nO
Carboxylic acids and esters CnH2nO2
Types of Carbons and Hydrogens :
Primary Carbon (1 carbon) : It is bonded to just one another carbon or to no other carbon.
Secondary carbon (2 carbon) : It is bonded to two other carbons.
Tertiary carbon (3 carbon) It is bonded to three other carbons.
Quaternary carbon (4 carbon) : It is bonded to four other carbons.
Types of hydrogens :
Primary hydrogen : Hydrogen attached to primary carbon.
Secondary hydrogen : Hydrogen attached to secondary carbon.
Tertiary hydrogen : Hydrogen attached to tertiary carbon.
1
CH3
1 2 3 | 1
Ex. CH3 CH2 CH C CH3
| |
CH3 CH 3
1 1

In the above structure, five primary carbons, one secondary carbon, one tertiary carbon and one
quaternary carbon are present. Similarly, the number of primary hydrogens 15, secondary
hydrogens 2, tertiary hydrogen 1, and there is no quaternary hydrogen.
IUPAC nomenclature:
IUPAC name of compound consists of
i) Root word ii) Suffix iii) Prefix
Root word gives the number of carbons in parent skeleton
Suffix gives the nature of the functional group
Prefix gives the nature of the substituent.
Side chains:
i) Alkyl: It contains one hydrogen less than that of alkane. Ex.
CH3 Methyl
C2H5 Ethyl
CH3 CH2 CH2 n propyl
CH3 CH
| iso propyl
CH3
CH3 CH2 CH2 CH2 nButyl
CH3 CH CH2
| Iso butyl
CH3
CH3 CH CH2 CH3
| Sec butyl

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 Organic Chemistry
CH3
|
CH3 C CH3 ter butyl
|
CH3 CH2 CH2 CH2 CH2 n pentyl (Amyl)
CH3 CH CH2 CH2
| Iso pentyl
CH3 (Iso amyl)
|
CH3 C C2H5
| Ter-Pentyl
CH3
CH3
|
CH3 C CH3 Neo Pentyl
|
CH3
Alkenyl : It contains one hydrogen less than that of Alkene.
Ex : CH2 = CH Ethenyl ( Vinyl)
CH3 CH = CH 1Propenyl
CH2 = CH CH2 Allyl
CH3 CH2 CH = CH 1Butenyl
Alkynyl: It contains one hydrogen less than that of alkyne
Ex: HC C ethynyl
H3C C C 1 propynyl
H3C CH2 C C 1 butynyl
When all the carbons are present in a straight chain, the alkane is called normal alkane.
When all the carbons are not present in straight chain, it may be called iso alkane.
Ex: CH3 CH2 CH2 CH3 n Butane
CH3 CH CH3 Iso butane
|
CH3
Root word :
No. of carbons: Root word
1 Meth
2 Eth
3 Prop
4 But
5 Pent
6 Hex
7 Hept
8 Oct
9 Non
10 Dec

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 Organic Chemistry
1. Longest chain rule : Select the continuous chain of carbons having maximum number of carbon
atoms.
2. Lowest sum rule: Gives the lowest possible numbers to the substituents and functional groups.
3. Longest chain rule can be violated to include the double bonds triple bonds, functional groups.
4. If two or more functional groups are present, senior functional group is given suffix and junior
functional group is given prefix.
5. If two or more different substituents are present at various positions, consider the lowest sum
irrespective of the nature of substituents.
6. If two similar substituents are present at identical positions from opposite ends, then follow
alphabetical order to give lowest number.
7. If two or more carbon chains having the same number of carbons are present then the chain having
more number of branches is selected as parent chain.
8. If the compounds contact more than one functional group the principal group form the suffix while
the other functional group is considered as the substitutent.
9. The preference order is COOH > Acid derivatives > CHO > CN > C = O > OH > NH2 > O
> C = C > C C.
Name Formula Suffix Prefix
Carboxylic acid COOH oic acid carboxy
Acid chloride COCl oyl chloride Chloro formlye
Acid amide CONH2 Amide Carbomyl
Ester COOR ate Alkoxy carbonyl
Aldehyde CHO al Aldo or formyl
Cyanide CN nitrile Cyano
Ketone C = O one Keto or oxo
|

Alcohol OH ol Hydroxy
Amine NH2 amine Amino
Ether O Alkoxy
C = C
Alkene | | ene ene
Alkyne C C yne yne

Substituents: Which are given only prefixes:

X (Cl, Br, I) halo
ONO nitrite
NO2 nitro
NO nitroso
OR Alkoxy
R Alkyl

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 Organic Chemistry
EXERCISES :
Structure IUPAC name
CH3
|
1. CH3 CH C CH3 2, 2, 3 trimethyl butane
| |
CH3 CH3
CH3 CH CH2 CH3

2. CH 2, 3 dimethyl pentane
CH3 CH3
CH3 CH CH CH
3. | | 2, 3 dimethyl pentane
CH3 C2H5
CH3 CH2 CH CH CH2 CH3
4. | | 3ethyl 4 methyl hexane
CH3 C2H5
CH3 CH2 CH2 CH CH2 CH2 CH3

5. CH 4 (1 methyl ethyl ) heptane

CH3 CH3
CH3 CH2 CH2 CH CH2 CH2 CH3

CH CH3 CH3
2, 3, 6 trimethyl 4 propyl
6.
CH CH3 heptane
CH3
CH3 CH2 CH2 CH2 CH CH2 CH2 C2H5

CH CH3
5 (1, 2, 2 trimethyl propyl)
7.
CH3 C CH3 nonane

CH3
CH3 CH CH2 CH3
8. 3 methyl pent 1 ene
CH = CH2
9. CH2 = CH CH = CH2 But 1, 3 diene
CH3 CH2 CH2 CH CH2 CH2 CH3
10. 3 propyl hex 1 ene
CH CH2
11. CH C CH = CH CH3 Pent 3 ene 1 yne
12. CH C CH = CH2 But 1 en 3 yne
CH3 CH CH CH3
13. | | 2 Bromo 3 chloro butane
Cl Br

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 Organic Chemistry
CH3 CH CH CH CH CH2 CH2 CH3
| | | 4 bromo 3 chloro 2 nitro
14.
NO2 Cl Br octane
15. CH3 O C2H5 Methoxy ethane
16. C2H5 O C2H5 Ethoxy ethane
CH3 O CH CH3
17. | 2 Methoxy propane
CH3
CH3 CH = CH CH CH2 CH3
18. | 4 Ethoxy hex 2 ene
OC2H5
CH3 CH CH3
19. | propan 2 ol
OH
CH3 CH CH = CH CH3
20. | pent 3 en 2 ol
OH
CH3
|
21. CH3 C OH 2 methyl propan 2 ol
|
CH3
CH3 CH CH CH2 CH3
22. 2 Methoxy pentan 3 ol
OCH3 OH
O
||
23. H C Methanal
|
H
24. CH3 CHO Ethanal
CH3 CH CHO
25. | 2 Methyl propanal
CH3
OH CH3
26. | | 3 Hydroxy 2 Methyl Butanal
H3 C CH CH CHO
CH2 CH CH CHO
27. | 2 Hydroxy But 3 enal
OH
CH3 C CH3
28. || Propanone
O
O
||
29. H3 C C CH CHO 3 keto 2 Methyl Butanal
|
CH3

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 Organic Chemistry
O
||
30. H C Methanoic acid
|
OH
CH3
31. | 2 Methyl propanoic acid
H3 C CH COOH
CHO
|
32. H3 C CH2 CH CH COOH 3 Aldo 2 Methyl pentanoic acid
|
CH3
COOH
33. | Ethan dioic acid
COOH
H C OCH3
34. || Methyl methanoate
O
35. CH3 COOC2 H5 Ethyl ethanoate
CH3 CH C O CH3
36. | || Methyl 2 chloro propanoate
Cl O
37. CH3 CH2 NH2 Ethanamine
CH3 CH CH3
38. | Propan 2 amine
NH2
CH3 CH CH CH3
39. | | 3 Amino Butan 2 ol
OH NH2

40. CH3 NH CH3 N methyl amino methane

41. CH3 NH C2 H5 N Methyl amino ethane
CH3 N CH3
42. | N, N Dimethyl amino methane
CH3
CH3 N C2 H5
43. | N, N Dimethyl amino ethane
CH3

44. H CN Methane nitrile

45. CH3 CN Ethane nitrile
CH3 CH CN
46. | 2 methyl propane nitrile
CH3
CH2 CH2
47. | | butane 1, 4 Dinitrile
CN CN

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 Organic Chemistry
CH2 CH2 CH2
48. | | | 3cyano pentane 1, 5 dinitrile
CN CN CN
COOCH3
CH2
49. Dimethyl propane dioate
COOCH3
CH2 COOCH3
50. Ethyl methyl butane dioate
CH2 COOC2H5

Common Name Structure

1. Acetic acid CH3 COOH
2. Formic acid HCOOH
3. Acetaldehyde CH3CHO
CH3 C CH3
4. Acetone ||
O
5. Vinyl cyanide CH2 = CH CN
6. Vinyl alcohol CH2 = CH OH
7. Acetonitrile CH3 CN
8. Methyl carbinol CH3 CH2 OH
CH3
|
9. Trimethyl carbinol CH3 C OH
|
CH3

CH3
|
10. Ter Butyl alcohol CH3 C OH
|
CH3
CH3 C Cl
11. Acetyl chloride ||
O
CH3 C NH2
12. Acetamide ||
O
13. Methyl acetylene CH3 C CH
14. Pyrene CCl4
15. Formaldehyde HCHO
16. Phenyl isocyanide C6H5 NC
CH3 C CH3
17. Dimethyl ketone ||
O
18. Ethyl acetate CH3OOC2H5
CH3 CH CH2 CHO
19. Aldol |
OH

18
 Organic Chemistry
20. Marsh gas CH4
CH3
|
21. 2, 2, 4 Trimethyl pentane H3 C C H2 C HC CH3
| |
CH CH
3 3
OHC HC = CH H2C H2C H2C
22. Hept 2 enal
CH3
23. Pent 3 en 1 yne HC C HC = CH CH3
HOOC HC H2C CH3
24. 2 Hydroxy Butanoic acid |
OH
CH3 CH CH3
25. 2 methoxy propane |
OCH3
OHC H2C H2C C CH3
26. 4 Keto pentanal ||
O
27. Ethyl methanoate HCOOC2H5
28. Ethoxy ethane C2H5 O C2H5
CH3 C Cl
29. Ethanoyl chloride ||
O
CH3 C NH 2
30. Ethanamide ||
O
CH3 CH CH3
31. Propan 2 amine |
NH2

32. N ethyl amino ethane C2H5 NH C2H5

C 2H5 N CH 2 CH 2 CH3
33. N, N diethyl amino propane |
C2H5

34. Ethane nitrile CH3 CN

35. Methyl carbyl amine CH3 NC

WRITING THE STRUCTURE OF THE COMPOUND WHOSE NAME IS GIVEN

(a) Observe the word root and write the continuous carbon chain.
(b) Number the carbon atoms in a suitable way and attach the functional groups, substituents and
multiple bonds at their respective carbon atoms.
(c) Carbon has tetravalency. Attach the required number of hydrogen atoms at each carbon atom to
satisfy its tetra valency. Now the structure is complex.
Example : 3 Bromo 2 Methyl pentan 2 ol
1 2 3 4 5
a) As per the word root pent we have C C C C C

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 Organic Chemistry
OH
|
1 2 3 4 5
C C C C C
b) As per the name | |
CH 3 Br
c) To satisfy the tetravalency of each carbon atom hydrogen atoms ate added to each carbon atom
as per requirement.
H OH H H H
| | | | |
HCCCCCH
| | | | |
H CH 3 Br H H
Hence, the structure is complete
Let us see the nomenclature of cyclic compounds.

Cyclohexene 3-Chlorocyclohexene Cyclohexyne Cyclohexan 1-ol

Nomenclature of substituted benzene compounds

The common names of the above compounds are given in brackets wherever necessary.
Substituents are mentioned in alphabetical order giving lowest number to the first substituent.

1) Methylbenzene IUPAC 2) Methoxybenzene 3) Bromobenzene

(Toluene) (Anisole)

4) 1, 2-dibromobenzene 5) 1, 3-dichlorobenzene 6) 1-chloro-4-nitrobenzene

(orthodibromobenzene) (metadichlorobenzene)

7) Benzene carbaldehyde 8) Benzene carboxylic acid 9) Styrene

(benzaldehyde) (benzoic acid)

10) Phenol 11) Acetophenone

20
 Organic Chemistry

Dimethyl derivatives of benzene are called Xylenes.

1, 2-dimethyl benzene (O - xylene)

Consider

It is named as 2, 4, 6 - trinitro toluene taking toluene as the base

name. Similarly is named as 4-ethyl - 2 - fluroanisole.

When no simple base name other than benzene is possible, the positions are numbered so as to
give the lowest locate at the first point of difference.

Example :

1-Chloro-2, 4-dinitrobenzene 4-ethyl-1-fluoro-2-nitrobenzene

(not 4-chloro -1, 3-dinitrobenzene)

If benzene ring is named as substituent it is named as phenyl . Similarly an arene is named as

aryl.

2-phenylethanol Benzyl Chloride

21