12.

26 DINESH cOMPANION CH
EXAMPLE 4
Write the IUPAC
names of the following compounas
) CH-ÇH-CH-CH, ( ) (CH)CCHs

CH CH
(iii) CH3-CH-CH-C-CH3 (iv) CH3-CH-CH2-C-CH3
CH2 CH CH CH
CH3
ÇzHs CH3 CH3
(v) CH-ÇH-¢-CH3 (vi') CH3-¢--CH-CH-CH3
CH CH3 H, CH2-CH
CH2-CH3 CH CH2-CH
(vii) CH3-CH-CH-CH2-CH2-CH, (vii) CH3-C-C- -CH-CH3
CH2-CH3 CH CH-CH, CH,
(ix) CH3-CH-CH-CH2-CH2-CH-CH2-CH (CH3)2
CH, CH CH2-CH2-CH2-CH3
CH(CH3)2
) CH3-¢-CH-CH (r CH-CH2-CH-CH2-CH3
CH3 CH-CH2-CH-CH-CH
CH-CH-CH,-CH,
Crii)
(xrii) CH-H-CH-CH-CH, (xii) CH3-CH2-CH-CH-CH2-CH-CH3
CH-H-CH,
CH, CH2 CH3
Solution.
CH-CH-CH
CH3
i) CH3-H-CH-CH3 Gi) H- H2- H,
2 s
CH¢H2 H3
'CHCH
2, 2-Dimethylbutane
3, 4-Dimethylhexane

CH3 iv) 5 CH3

(ii) CH- H- H2-c- H
5CH2 CH3 CH3 CH3
6CH3
2. 2, 4-Trimethylhexane 2. 2.4-Trimethylpentane
 nistry-Some Bas Principles & Techniques 12.27
n i cC h e r

4
CH-CH3 CH CH3
vi) H_ 4
CH-CH--CH,
CH-H-CH3
CH CH3 CH3 CH2-CH3
3.3-Trimethylpentane
3-Ethy1-2, 2. 4-trimethylpentane

CHCH3 5
CH3 CH2-CH3
CH-CH-CH-CH2-CH;-CH3(vi) H,2 H-H3
CH2-CH3 H CH2-CH3 CH3
4-Ethyl-3-methylheptane 3, 3-Diethyl-2, 2, 4-trimethylpentane

CH3
a CH-CH-H-H2-H-H-H2CH-HJ
CH CH3 CH-ÊHHz-CH,
2.3-Dimethy1-6-(2-methylpropyl) decane

1CH3
2CH-CH3
fvi CH3-CH2- H-ÉH2- H3
tCHc- H2- H3 ri')
CH-CH-H-H2-Hg
CH3
2.3, 3-Trimethylpentane 3, 4-Diethylhexane

CH-H-H2-H3 7 6 5 2
4
ti) CH3-CH-CH-CH2-CH3 rin) CHg--H2-CH- CH-CH2CH-CH3
21
CH3-CH-CH3 CH CH2 CH3
HCH-CH3
2, 5-Dimethyl-4-(2-methylpropyl) heptane
3-Ethyl-2, 4, 5-trimethylheptane
for IUPAC Nomenclature of Unsaturated Hydrocarbons (AIkenes and Alkynes)
.In Rules rules are to be followed in addition to the rules already listed.
writing the IUPAC names of such hydrocarbons, following
bond regardless of the fact whether it is longest continuous chain or not. For
he parent chain must include the multiple
ample,

CH-CHCH-CHCH-CH3 CH3-CH2-CH-CH2-CH2-CH3

CH=CH2 CH=CH2
Parent chain excluding double bond has
arent chain including double bond has
six carbon atoms (wrong)
SIX carbon atoms (correct)
In wrling the IUPAC name of a particular member of the alkene or alkyne family, the primary suffir 'ane' of the
Tespondinnumberit
g alkane
. The umbering
ne is replaced by 'ene' or 'yne' respectively.
of the parent chain must be done in such a way that the first C-atom involved in the multiple bond gets
* lowest number.

AtAccordi
medthevately nbefore
g to
t o the latest IUPAC convention, the locants for the multiple bonds (double or triple bonds) are placed
suffixes (ene or yne) which they represent. The earlier practice was to place the locant either
the
primary
O r d root or after the name of the primary suffix but it is not regarded as proper. For example,
 12.28 DINESH cOMPANION CHEMIST
STR
CH-CH2-H=CH2 CH--H,
But-1-ene (Correct) But-2-yne (Correct)

1-Butene (Not proper) 1-Butyne (Not proper)

Butene-1 Not proper) Butyne-1 (Not proper)
4 t h e selected principal or parent chain contains two (or three) double or triple bonds, then the primary suiT.
(or triene) or -diyne (or triyne) are used to represent these. In all these cases, ierminal 'a' is also added to the word r
uffiu dien
rool.
example,
CH-H=H-H=CH2 CH,-H,-aH
Penta-1, 3-diene Hexa-1, 4-diyne.
5. If the parent chain includes both double and triple bonds, then the following points must be kept in mind.
(a) The unsaturated compound is always named as a derivative of alkyne i.e., primary sujix "ene' always comesbé
yne. In all such cases, the terminal 'e' of 'ene' is dropped if it is followed by the suffix starting with a, i, o, u, ory.
example,

HC--H2-H=CH, HC-CH2-H2-ÉH=CH
Pent-1-en-4-yne Hex-1-en-5-yne
(preference to the locant for ene) (preference to the locant for ene)
(b) In case, the numbering from two different ends gives two different sets of locants, then the lower set of locms
preferred. For example,

CH-CH-H-aCH HJ-H=H--H
Pent-3-en-1-yne (Correct) Pent-2-en-4-yne (Wrong)
6. 1f the unsaturated hydrocarbon contains a side chain (or substituent) along with the multiple bonds, then the numberig
is
way that the multiple bonds get the lowest set of locants. However.
the in such a
parent or principal chain done
numbering from both ends gives the same set of locants to the multiple bonds, then the locant for the substituent must t
i
minimum. For example,

CH3 CH3
5 4 4
CH=H-CH =C-H3 CH=H-=CH2
4-Methylpenta-1, 3-diene
2-Methylbuta-1, 3-diene
(Lowest set of locants for double bonds) (Minimum locant
for CH3 substituent)
In some cases, more than two double bonds are present in the or hem
hydrocarbon and it is not possible to include all u
in the parent chain. In such cases, the following prefixes are used for the
double bonded groups not involved in the cha
CH2 CH-CH= CH=CH CH-CH-CH
(Methylidene) Ethylidene) (Vinyl or ethenyl)
(Allyl)
A few examples are listed as follows

CH2 CH=CH2
3
CH=H-c-H=H, CH-HH-H=H2
3 4

3-Methylidenepenta-1, 4-diene
3-Vinylpenta-1, 4-diene
(or 3-Ethenylpenta-1, 4-diene)
Note: The prefixes vinyl and allyl are used only in case these are not further substituted.
EXAMPLE 5

Write the IUPAC names of the following:

( (CH)2CH-CH=CH2
CH-CH
(Gi) CH2=CH-H-CH2-C=CH
(i) CH =C-CH-CH-CH=CH-CH (iv) (CH),C-CH=CH
ncChemistry
y-Some Basic Principles & Techniques 12.29

CH3
al HC-CH-CH-C=CH
(vi) CH-C=C-CH-CH-CH=CH2

CH=CH2
niCH-CH-C-C-CH
CH-CH=CH2 (vii) CH2=CH-CH(CH)2
CH2
CH-CH3
CH3
a)CHC-CH-CH (CH=-CH2-CH2-CH3
CH-CH3 CH(CH)2
CH3
CH=CH2
i(CH),C-CH=CH Cxii) CH(CH,)2CH(CH2), CH3
Solution.
CH3 CH2-CH3 5
3 6
CH-CH-H=H2 Gi) CH=H-CH-H2-c=H
3-Methylbut-1-ene 3-Ethylhex-1-en-5-yne
CH3
CH- H- H2- H= H- H, Civ) CHy- H- H,
Hept-5-en-1-yne CH3
3, 3-Dimethylbut-1-ene

CH3
CHCH-CH-=H 0oi -i-¢H-H2-H=H
CH=CH2
4-Vinylhept-1-en-5-yne
3-Methylpent-1-en-4-yne (or 4-Ethenylhept-1-en-5-yne)

CH-H-H-H-CH2 (vi) H,=H-H-H

---
1CH2 CH
3-Methylbut-1-ene
2CH-CH3
3CH3-

-(2-Methylpropyl)hept-1-en-4-yne
y CH--CH-CH3 CH- H,- H2- H,
H-CH3
CH-CH 2CH3
2-(1-Methylethy)pent-1-ene

2-Ethy1-3-methylbut-1-ene
CH3
CH-CH,
CHy-CH-CH-CH-CH-CH-CH2-CH,

CH3
3-Propylhept-1-ene
3,3-Dimethylbut-1-ene
 C. IUPAC Nomenclature of the
compounds containing secondary prefixes (or substituents) other tha
alkyl groups
ne list of such substituents is given in the general discussion of IUPAC nomenclature. These are never
principal functional groups or secondary suffixes. These are named in an alphabetical order along with the alkv
present. For example, grouaps
CI CI Br
2 3
CH-C-H2-H3 CH-CHCH-H2-H
2-Chlorobutane 3-Bromo-2-chloropentane

CH3 NO2
CH-CH-H2-CH-H CH-H=H -CH-H3
5

2-Methyl-4-nitropentane 4-Iodopent-2-ene
ÇHCI CHCI CH,Br
CH-CHCH-H2-H, 4 3 2

3-Chloromethylpentane
H-H2-H-CH-CH2-CH3
3-Bromomethyl-4-chloromethylhexane
CH
2 2
CH-0-CH-H2-H; CaHO-CH2-CH2-OC,Hs
2-Methoxybutane
1,2-Diethoxyethane

CI
CH3 CH3
5 4
CHC-H-C-CH3 CH¢-H,¢-CH3
NO2 I
CH 'CH3
3-Chloro-5-fluoro-3, 5-dimethylheptane
3-lodo-3, 5-dimethyl-5-nitroheptane.
CI
CH-CH-H_C-CH, Br Br

2-Chloro-3-ethylpenta-1, 4-diene
CH,-C-E-CH2-CI
D. lUPAC Nomenclature of the 2,3-Dibromo-1, 4-dichlorobut-2-ene
compounds containing one
The IUPAC names of these
compounds are based on the Functional Group
1. Select the following rules.
or
Secondary Suffix.
longest chain containing the carbon
chain or principal chain. atom to which the
functional group is attached. This isis know
known as
CH-CH2-CH-CH2-CH2-CH
CH2-OH
Parent chain does not include the
Cl1-CH-CH-CH2-CH2-ClHl
CH2 OH
functional group bearing carbon Parent
(wrong) functional groupchain includes the
bearing carbon
(correct)
ganic Chem/stry-Som
Some Basic rinciples &
Techniques 12.31

he ring of the carbon atoms in the

parent chain is done in such way that the carbon aton
a Dedr 6
T h e

loHest
number, "
the
weis
for naming the substituents (or side chains) are followed. These are the same as described earlier.
other rules Jor naming
itustrate these rules with the help of a few examples.
Let us u

CH3 CH3
CH-H2-H-H, 21
CH3 OH
CH-H-H,-H,
CH3 OH

4,4-Dimethylpentan-2-ol
2,2-Dimethylpentan-3-o
CH3
CH -H-H2-H CH,-H,-¢H-CH,
CH NH2 H3
CH3
4,4-Dimethylhexan-3-amine 2-Methylpentan-3-one
4 If the organic compound contains terminal functional group (secondary suffix) such as-CHO, -COOH, -COC,

NH-COOR, -C=N etc.. the numbering of the parent chain must start from the group carbon atom.
functional
broer, is number is generally not mentioned in the IUPAC name of the compound. For example,

CH3 CH3
CH-CH-H-CH-H,-H, CH -¢H-H,--OH
CHO CH Br
3-Bromo4, 4-dimethylpentanoic acid
2-Ethy1-3-methylpentanal

CH-CH-ÉH2--NH2 CH-CH-H2--C
CH-CHs Br

3-Bromobutanoylchloride
3-Methylpentanamide
4
2 CHy-CH-H,--oCH,
CH3-CH-H2-=N
Butanenitrile CaHs
Methyl-3-methylpentanoate

the numerical prefxes di, tri, tetra etc. are used to indicate
contains two or more similar (like) groups,
andmpound inal 'e"from the primary suffix is retained while writing the IUPAC name. For example,
the termina

H-HH CH- H- H2 CH-ÉH-H

OH OH OH ÖH NH2 NH2
OH Propane-1, 3-diamine
Propane-1, 3-diol Propane-1, 2, 3-triol

HO-C H2- H,- -OH CH-H2--H

Pentane-2, 4-dione
Butanedial Butanedioic acid
 DINESH COMPANION CHEMISTRY
12.32
terminal groups (Special cases)
more than two similar
TOPAC names for compounds containing
all of them are directly attached to th
he
than two similar terminal groups and
lt the organic compound contains more suffixes are used to name these.
chain. Special
then of them forms a part of the parent
parent or principal chain, none

Special Sufix
Functional group
Carboxylic acid
-COOH

-CHO Carbaldehyde
Carbonitrile
-C=N
Carboxamide
-cONH2
are not counted in the principal or parent chain,
terminal groups
It may be noted that the carbon atoms of these
A few examples of such compounds are given:

CHO COOH
OHC-CH-H2-CH-H2-CHO HOOC-H-H-H2-CoOH
Butane-1, 3, 4-tricarbaldehyde Propane-1, 2, 3-tricarboxylic acid

CN cONH2
N=C-H-CH-H-CoN H,NOC-CH2-CH-CH-CONH2
Propane-1, 2, 3-tricarbonitrile Propane-1, 2, 3-tricarboxamide.

Note: If any one of these terminal groups is not directly attached to the parent chain and forms the part of the side

chain, then the chain is selected in a such a way so as to include two such similar groups at its two ends. T
longest
groups present in the side chain are treated as substituents and are indicated by suitable prefixes. For example,

CH2-COOH CHCHO
HOO-ÉH2-CH-H2-ooH OHC-CHCH-CH2-HO
3-(Carboxymethyl) pentane dioic acid 3-(Formylmethyl) pentanedial

EXAMPLE 6

Write the IUPAC names of:

CH2=CH-CH-CH3 (i) CH3-CH-CH-CH-CH3

OH NO2 OH

OCH3
(ii) CH30-CH-CH2-CH3 (iv) CH-CH2-0-CH2-CH2-Br

(v) CH2-CH-CH--H (vi) CH-CH=CH-CHO

NO2

(vii) CHs-CH=CH-CoOH (vii) CH3-CH--CH-OCH

CH3 CH3
(ix) CH-CH=CH-CH-NH2 () CHyCH)NH;
 Principles &Techniques 12.33
-Some Basic
ic Cnemistry-Some

a i C H - C H - C O - C H
(rii) CH3-CH-CH-CH3

CHs CH3 COOH

CH3
CH-CO-CH-CH-CH2-CI (Cxiv) CH3-CH2-CH-C-CH-CI
Br Br
CH-CO
in) C H - C H - C H - C O C
(rvi)
CH-CH-co
Solution.
CH
(in CH-CH-CH-CH-CH3
oH,=H-H-H
OH
NO, i OH
But-3-en-2-ol 3-Iodo-4-nitropentan-2-o
OCH3 2
CH,0- H-- H2- H, iv) CH3-CH2-0-CH-CH2-Br
1, 1-Dimethoxypropane
1-Bromo-2-ethoxyethane

CH-H-ÉH --H (CH-H-H-HO

NO2 But-2-enal
4-Iodo-3-nitrobutanal

3l 4
(vil) CHg- H- -CH-OCH
i cyH,-CH=H-COOH
H SCH3
2-Methy1-4-methoxypentan-3-one
3-Phenylprop-2-enoic acid
2
)CcHs-CH,-CH-NH
li CH-H-H-Hh-NH2 2-Phenylethan-1-amine
But-2-en-1-amine

Cxin CH-CH- H2- H,

CH-H¢H-H coOH
CH3 CH3 2-Methylbutanoic acid
2,4-Dimethylpentan-3-one
CH3
-CH- H,- H-CI (tiv) H-H-H-¢-H,-CI
Br Br
CHs 2, 3-Dibromo-1-chloro-2-methylpentane

-Chloro-3-ethylpentan-2-one
CH-CO

H,-CH,-CH--C xvi)
CH-CH2-C0

CH3 Ethanoicpropanoic anhydride

2-MethylIbutanoyl chloride
 12.34 DINESH cOMPANION CHEMISTR,
containing more than one different functional groups (Poly Functie
E. IUPAC Nomenclature for compounds
Compounds) then one of these is selected as ne
different functional groups,
wnen anorganic compound contains two or more
Tunctional group while the others are called secondary functional groups
and are treated as substituents. The choiceofnte
order of preferences
principal functional group is made on the basis of the following ester acyl halide > acyl amide
acid anhydride
Carboxylic acid sulphonic acid >
nitrile > aldehyde> ketone > alcohol> amine> alkene> alkyne.
nitro (- NO;), alkoxy (-OR)
are treated as substn
The remaining functional groups such as halo (- X), nitroso (- NO),
groups or simply as prefixes.
with the maximum preference (princ
functional compound, the functional group
Inwriting the IUPAC name of a poly the word root along with the primary suffix. All te
suffix which is added to
functional group) is represented by the secondary added to the root word.
indicated by suitable prefixes which are
groups, if present,
are
secondary functional upon its priority
in the priority sequeti
or a prefix depending
a secondary suffix
Thus, functional group can act either as
a and the other while acting as a prefix.
as secondary
suffix
has two names; one while acting
A functional group, in fact,
Name as prefix
Name as secondary suffix
Functional group functional group)
(or secondary
(or principal functional group) carboxy
-oic acid
-COOH
sulphonic acid sulpho
-SO3H
- oic anhydride
alkoxycarbonyl
alkylalkanoate
-cOOR
- oyl halide
haloformyl
-COX carbamoyl
- amide
-CONH2 cyano
- nitrile
-C = N formyl (or aldo)
-al
-CHO keto or oxo
one
hydroxy
-ol
-OH - amine
amino
carbon atom Cn
-NH2 both sides of the
groups attached
on

contains both
-CHO and-COOH
suffix is oic acid.
At the same u
an organic compound functional group and its secondary
Suppose the principal
regarded as
group is formyl as shown below:
Then-COOH
substituent and its prefix is
- C H O group
is the
functional group
(OHC-CH-CH,-CH-cooH) Principal
Substituent (oic acid)

(formyl)
4-Formylbutanoic acid
compound is:
The IUPAC
of the
name
compounds are as
follows:
polyfunctional
examples of such
Some other

OHC- H2- H2- H,- =N

CH H- H,-H
(-C=N is principal
functional group)
functional group)
(-CHO is principal 4-Formylbutanenitrile
4-ketopentanal
O
OH
CONH2 CH-CH-CH,--H,
H- H H-ÉH,- ooH

(>C =O is principal functional group)

functional group)

is principal 4-Hydroxypentan-2-one
(-COOH
3-Carbanoylpentanoic acid
 Chemistry-Some Basic Principles& Techniques
anic 12.35

NH2 OH
1 2 3 4
2 1 HOOC-ÇH-CH-coOH
CH3-CH-CH2-CH-CH
OH OH
(-OH is principal functional group)
(-coOH is principal functional group)
4-Aminopentan-2-ol
2,3-Dihydroxybutanedioic acid
2 NH2 1
OHC-CH-CH2-C-CH2-COOH
-coOH is principal functional group)
HCH-H,-HOH-CH
(-OH is principal functional group)
5-Formy1-3-oxopentanoic acid
4-Aminopentan-2-ol

CH-CH-H2-ONH2 CH-CH-H--H=H2
2
CN OCHs Br
cONHCHs
-CONH is principal functional group) -cONHC>Hs is principal functional group)
4-Cyano-3-ethoxybutanamide 2-(2-Bromoethyl)-N-ethyl-3-oxopent-4-enamide
CoOH CH3
l2 21
HOOC-CH-C-CH-coOH CH NH-H2-H2-¢-CH2-CH3
NH2 CHO
-COOH is principal functional group) (-CHO is principal functional group)
2-Aminopropane -1, 2, 3-tricarboxylic acid 2-Ethyl-2-methyl-4-N-methylaminobutanal
14. Writing the Structural Formula from the IUPAC Name of the Compound
We have, so far, discussed how to write the IUPAC name of an organic compound if its structure is given. Now let us study
ETSe i.e.,
Teverse i write the structure of an organic compound if its IUPAC name is given. This can be done as follows
Select the parent chain with the help of the word root as indicated by the lUPAC name of the compound.

) Number the parent chain starting from either end.

or principal functional group from the 1UPAC name of the
ldentify theand position of the secondary suffir
name
chain.
compound and fix it at appropriate position in the parent
the 1UPAC name and also attach them at the proper
dentify the names and positions of others prefixes, f any, from
pOsitions in the carbon atom chain.
n case, the name of the compound contains -ene or -yne, then jill double or iriple bond at the indicated position.
wherever necesSay, to satisfy the tetracovalency of each
Finally, attach the required number of hydrogen atoms,
carbon atom.
write the structural tormula or 4-Hydroxy-2-methylpent-3-enoic acid, It is
aSIs of the above discussion, let us
Peed in the
following steps has five carbon atoms.
Th ord root pent indicates that
the parent chain
C-C-C-C-C

i) umber the chain from any end

ofcarbon atoms
c--C- -c
i) Th carbon atom
of-COOH group is indicated as 1.
and the
Condary suffix is oic acid
HO-C-C--
 DINESH COMPANION CHEMSTR
12.36

at the positions 4 and 2 respectively.

(v) Attach the prefixes hydrory and methyl

CC-C-C-C
ö CH3 OH
suffix ene at position 3. Therefore, fill double bond between poi
() The IUPAC name of the compound has primary
3 and 4
HO-C-- -c-c
o CH3 OH
final structure.
atoms to various carbon atoms to get the
(vi) Attach the required number ofhydrogen
HIH H

HO-
CH3 OHH
EXAMPLE 7
Draw the structures of the following compounds.
i) Hex-3-enoic acid (ii) 2-chloro-2-methylbutan-1-o
(iv) Propane-1, 3-diamine
(ii) 5, 5-Diethylnonan-3-ol
(vi) But-2-ene-1, 4-dioic acid
(v)4-Nitropent-1-yne
(vii) 4-Amino-2-ethylpent-2-enal (vii) Ethyl-3-methoxy-4-nitrobutanoate
-(1-Methylethyl)-3-methyloctane r) Her-4-yn-2-one
ri) Hepta-1, 4-dien-3-ol (rii) 4-Chloropent-2-ene
(rii) 1-Phenylpropan-2-one. (xiv) 4-Ethyl-2, 6-dimethyldec-4-ene.
Solution.
Ci
21
CH- H-CH= H- H,--OH (i) H-H-¢-CH2-OH
CH3
C2Hs
3 2
i) CH-CH-CH-HJ-H;-H-H2-H, ) H2-H-CH
2Hs OH NH2 NH2
2
)CH-CH-CH-C=CH vi) HOOH=H-CoOH

(vii) Hy-CH-H = H 2
(vii) HC--CH-CH- -OCHs
NH2 CHs NO OCH
6 4 3 2 1
(z)CHy-CH,-CH-CH-CH-CH-CH-CH, CH--H,-H,
CH-CH3 CH3
3
ari) CH-CH2-CH=CH-CH-CH=CH, 4
(ai) CHg-CH-H=H-CH
OH
O
CI
2 3 9
exii) CgHs-CH2-C-CH3 civ) CH-CH2-CH-CH-CH-H=ç-CH-H-H 6

CH3 CHs
 hemistry-Some Basic Principles & Techniques 12.37

Nomenclature of Aromatic Compounds

15

earlier
ier study
study of the organic chemistry. many pleasant smelling compounds were obtained from some natural sources
In the oinds were found to be quite different from the aliphatic compounds in their characteristics. On account of their
s compounds

these compounds were regarded as aromatic (Greek aroma of their

ndour. pleasant smell). An =
investigation
revealed that these compounds resembled benzene (C^H) which has a ring structure involving six carbon atoms
benzene in their
ATures

of organic
h the development a large number of
chemistry. compounds were discovered which resembled
had unpleasant
but smel. Therefore, the word 'aroma' lost its significance. According to the latest
casture or irritating
i n order that a compound may be aromatic, it must fulfil the following conditions.
The compound must be cyclic in nature with one or more n electrons in conjugated positiops.
d The compound must take part in the substitution reactions and resist addition and oxidation.
a) lte must be flat and must have tendency to show resonance
to
(iv) But the most important
criteria for aromatic character is that the compound must obey Huckel's rule. According
2) r electrons whe e n may be 0,
the rule, a cyclic compound wilI behave as aromatic compound if it contains (4n +

1, 2, 3, etc.
and
In the light of the above discussion, aromatic compounds may be classified into two main types. These are benzenoid
a0-benzenoids.
but fused together. A few
Benzenoids. These are cyclic compounds which contain in them either one or more benzene rings
umples of benzenoids are as follows

Benzene Naphthalene Anthracene Cyclooctatetraene

6.7 electrons (n = 1) 10 7 electrons (n = 2) 14 7 electrons (n = 3) 8 t-electrons

(Aromatic) (Aromatic)
(Aromatic) (Non-aromatic)
bonds in the alternate positions is not the sole criteria for a compound to be aromatic.
noted that the presence of double
may be cyclooctatetraene
t
rr ekample, contains four double bonds in the alternate positions but is non-aromatic because the number of r-

EUtons (eight) is not according to Huckel's rule.

a benzene ring but they
fulfil the characteristics of aromatic
Non-benzenoids. Certain compounds do not contain class of aromatic compounds. For
compounds belong to this
pounds. These are called non-benzenoids. Some heterocyclic
Nample,

H
Thiophene Pyridine
Pyrrole Furan
certain ions also behave as
aromatic compounds. For example
ltmay
De noted that only the molecules but even

H
H H
Cycloheptatriene
Cyclopentadiene
Cation
Cyclopropene Anion
Cation (6 T-Electrons)
(6 7-Electrons)
(2 7-Electrons) aromatic h ccontain
compounds which one or more benzene
Nome We have studied
that benzenoids
are
the
gS. enature of Benzenoids. with single and doubie
bonds in the alternate positions. It can be represented
onal rino ofcarbon atoms
y Of the following structures.
CH
H CH or
or
R S i d e chain
HC CH
CH structures. The ring is
of the other two
t of the the last is a hybridatoms attached to the carbon atoms of
calngledare nucleus.
substut
structures
ructures given
n c a s e any
above,
give or m o r e
one
hydrogen

groups
side chains.
then such groups
form the Ring
ued by some alkyl (R)
 12.38
DINESH COMPANION CHEMISTR organic Chemistry--Some Basic
Nuclear and side chain substituted
Aromatic Compounds.
TRIK
Nuclear substituted These are the compounds formed by substituting one or more gen atoms
hydrogen atoms in CH3
functional groups (or substituents other than alkyl groups). in the
ring huby surah,
ring
CH2-X
CH3
1. 4-Dimethylbenzene
Nuclear substituted Side chain substituted (p-Xylene)
aromatic compound aromatic compound CH3-CH-CH
Side chain substituted: These are the compounds formed by substituting one or more
chain by suitable functional hydrogen atoms in the allvl s
groups substituents.
or
Naming the substituted Benzene Derivatives
We know that in the benzene Isopropylbenzene
ring each carbon atom has a hydrogen attached to it. By substituting these
with
substituents, different substituted products can
one or more
be formed. Let
hydrogen atm (Cumene)
us try to nanme some of these. Aromatic hydrocarbons may al
Monosubstituted : Since all the carbon atoms in the ring are identical, by replacing
them, only one monosubstituted derivative will be formed
a
hydrogen atom attached to any

or or or

Diphenyl
2. Aryl groups. An aryl gro
(All monosubstituted derivatives are the same) example,
Disubstituted: disubstituted derivative can be formed by substituting
A
any of the five
monosubstituted derivative by suitable substituents (x). available hydrogen atoms
in d

Phenyl
Phenyl (C,H5-) is also somet
However, these representations are
ortho (or 1, 2) meta (or 1, 3) 3. Halogen derivatives. The
para (or 1, 4) same as (II) same as (1)
() (I1) upon whether hydrogen atoms of the
(II) (TV (V)
It may be noted that the arabic numerals are used in the IUPAC
names while the specific prefixes ortho (0-), meta
para (p-) are used for the common names. The aromatic are compounds generally known by their common names
commercial names in some cases. Nuclear substituted
Tri and bhigher substituted. These are
generally represented by the arabic numerals as shown below.
Chlor

. 4
Side chain substituted:
1. 2.3-trisubstituted 1,2,4-trisubstituted 1,3, 5-risubstituted 1, 2,
Now let us write the IUPAC and common names (given in 3, 4-tetrasubstituted
brackets) of a few important members of different Benzyl
aromatic compounds. a . Hydroxy derivatives. The
1. Aromatic hydrocarbons (arenes). The parent member is calla nown as aromatic
benzene and the substituted alcohols.
arenes. benzene derivative
Nuclear substituted (phenols).
CH3 CH3 CH3 OH
CH
Benzene Toluene 1, 2-Dimethylbenzene
e CH
1, 3-Dimethylbenzene
(o-Xylene) (m-Xylene) Phenol
 Chemistry-Some Basic Principles & Techniques .39

CH3
CH
CHCH3
H,c 2 CH
CH3
1.4-Dimethylbenzene 1,3, 5-Trimethylbenzene Ethylbenzene
p-Xylene) (Mesitylene)
CH-CH-CH3 CH2-CH=CH2 CH=CH2

Isopropylbenzene Allylbenzene Styrene

(Cumene)
Aomatic hydrocarbons may also contain more than one ring fused together.

Anthracene Phenanthrene
Diphenyl Naphthalene
hydrogen atoms in the ring or side chain. Foi
2. Aryl groups. An aryl group is obtained by removing one or more

umple,
H
-CH2

Benzal Benzo
Phenyl Benzyl as o-CH2-p.
sometimes indicated as p-. Thus, benzene can be shown as - H and diphenylmethane
PDenyl(CgHs-) is also
VEr, these representations are rarely used these dayS
or side chain substituted depending
derivatives may be either nuclear substituted
S Halogen derivatives. The halogen the have been substituted.
Er
hydrogen atoms of the ring or alkyl side chain
CI Br CH3
Br
Nuclear substituted Br
1, 2-Dibromobenzene 3-Bromotoluene
Chlorobenzene
(0-Dibromobenzene) (m-Bromotoluene)

CH2-Cl CH- H- H-CI CH=H-CH,-Br

de chain substituted
1-Chloro-3-phenylpropane 3-Bromo-1-phenylprop-1-ene.
Benzyl chloride
d e r i v a t i v e s are called phenols while the side substituted ar
4.Hydroxy
roxy derivatives. The nuclear substituted
hydroxy
2 aromatic alcohols. is also called phenol.
NucleaSubstituted (phenols). The first member of the family
OH OH
OH OH
OH
OH

Benzene-1, 2-diol
Benzene-1, 3-diol Benzene-1, 4-diol
Phenol (Resorcinol) (p-Quinol or hydroquinone)
(Catechol)
 12.40
DINESH cOMPANION CHEMISTY
STRY organ
OH OH OH

OH OH
OH HO
4
OH
Benzene-1, 2, 3-triol Benzene-1, 2, 4-triol Benzene-1, 3, 5-triol
PyrogalloB) (Hydroquinol) (Phloroglucinol)
OH OH
OH 8.

B ON -NO2

CH3 NO2
4-Methylphenol 2-Bromophenol 2,4, 6-Trinitrophenol
(p-Cresol) (o-Bromophenol) (Picric acid)
CH2-OH H2-H2-OH
Side chain substituted:

Benzylalcohol 2-Phenylethanol
5. Aldehydes.

CHO CH2-HO CH-H,-H2-HO

Benzaldehyde 2-Phenylethanal 4-Phenylbutanal
(Phenylacetaldehyde)
6. Carboxylic acids.

coOH ÇoOH 9.
COOH
2CH -OH

Benzoic acid 2-Methylbenzoic acid 2-Hydroxybenzoic acid

(o-Toluic acid) (o-Salicylie acid)
COOH ÇOOH COOH
-coOH

COOH
Benzene-1, 2-dicarboxylic acid Benzene-1, 3-dicarboxylic acid
COOH
(Phthalic acid) (Isophthalic acid) Benzene-1, 4-dicarboxylic acid
(Terephthalic acid)
7. Acid derivatives. (M
COCI CONH
CO

Benzoyl chloride Benzamide

Lco NH
Phthalimide
 Some Basic
nic Chemistry-Some Ba
Principles& Techniques 12.41

COOCH3

Methylbenzoate Benzoic anhydride

Phthalic anhydride
A m i n e s .

NH2 ÇH3 CH3

NH2

Benzenamine 2-Methylbenzenamine NH2

(Aniline or aminobenzene) (0-Toluidine) 4-Methylbenzenamine
(p-Toluidine)

HsC6 CgHs
NH-CH3 NH-CHs

N-Diphenylbenzenamine
N-Methylbenzenamine
N-Phenylbenzenamine
(N-Phenylaniline or (Triphenylamine)
(N-Methylaniline)
Diphenylamine)

CH2-H2-NH2 H2-H2-H2-NH2
CH2-NH2

3-Phenylpropan-1-amine

2-Phenylethanamine
Benzylamine
9. Ethers. -CgHs
0-CH3 0-CHs

Phenoxybenzene
Ethoxybenzene (Diphenylether)
Methoxybenzene (Phenetole)
Anisole)
10. Ketones.
O

-H3
Diphenylmethanone
Benzophenone)
1 - P h e n y l p r o p a n - 1 - o n e
ketone or
(Diphenyl
ketone)
1-Phenylethan-1-one (Ethyl phenyl
Methyl phenyl ketone
Acetophenone)

. Nitro compcunds.
CH3
NO2 O2N- NO2
NO2

NO NO2
2,4, 6-Trinitrotoluene

1, 3-Dinitrobenzene
Nitrobenzene (T.N.T.)
(m-Dinitrobenzene)
 12.42
DINESH cOMPANION CHEM
12. Sulphonic acids.

SO3H SO3H

-SO,H
Benzenesulphonic acid Benzene 1, 3-disulphonic acid
... (m-Disulphonic acid benzene)
Cyanides &
Isocyanides.
C=N NSC

Phenylcyanide Phenylisocyanide
:4. Diazonium salts. (Phenylcarbylamine)

N=NCI N=NHSO

Benzenediazonium chloride Benzene diazonium hydrogen sulphate

15. Grignard's reagents.

Mg-Br Mg-I

Phenyl magnesium bromide Phenyl magnesium iodide

16. Nomenclature of Polyfunctional Aromatic Compounds
The nomenclature of the polyfunctional organic compounds is based on the following
(i) In than one different functional
case more guidelines.
groups are present in the ring, these are
as discussed in case
of aliphatic
compounds. The group which is preferred is assigned priorities which are the ur
while the others are the substituents. For
example, regarded as the principal functional gm
COOH CHO
ÇOOH

3-Aninobenzo
NH :cid sOgH
OH
(it) If some prefixes are present
4-Hydroxybenzaldehyde 3-Carboxybenzenesulphonic acid
alongwith the functional groups, these are named in
have been numbered properly an alphabetical order altetr tk
CHO OH
NH2
NO2 NO2
CI C
4-Chloro-2-nitrobenzaldehyde 3-Bromo-2, 4-dichlorophenol Br
(ii) In case an alkyl group is one of 4-Bromo-2-nitrobenzenamine
the substituents, it is included in the name of the oun
named as the derivative of that particular arene. For parent arene and the co
example,
CH3 Ç2Hs
CH(CH3)2
No
3-Nitrotoluene 4
Br

CI
4-Chloroethylbenzene
2-Bromoisopropylbenzene
anic Cnemistry-Som asic Principles& Techniques 12.43

AMPLE8
he JUPAC names of the following compounds.
Cl

CH-CHOH ÇH-¢-C
C

CH-CH-NH; -CH,CI
(iv)

CHs
-CH-CH3
CH, OH
(v Cl -CH-c a
NO2
(vit ON NCH)
NH -NO2

i) HOOC coOH --CHCH

Solution.
) 2-Phenylethanol (i) 1, 1, 1-Trichloro-2, 2-diphenylethane
iv) 2-(Chloromethyl) chlorobenzene
(i) 2-Phenylethanamine (vi) 1,2-bis (4-chlorophenyl) ethane
() 3, 3-Diphenylbutan-2-ol (vii) 4-Nitroso-N-dimethylbenzenamine
(vi) 2, 4-Dinitrobenzenamine
acid ()1-Phenylpropanone.
() Benzene 1, 4-dicarboxylic
17. Nomenclature of Alicyclic Compounds aliphatic compounds in their
carbon atoms and resemble
one or more rings of three or more
Ihese compounds contain alicyclic compounds.
-ceristics. These are therefore, called aliphatic cyclic or

Monocyclic Compounds based on the following rules.

DEnames of the alicyclic compounds
are
obtained by adding the primary prefix
"cyclo' to the word root that
are
The names of the compounds
alicyclic
Esponds to the number of carbon atoms in the ring. suffix 'ane' is added to the word root. For those
the ring, primary
all single bonds in
ne cyclic compounds containing suffix ene or yne is added.
g O n e double or triple bond, the primary

Cyclopentane Cyclohexane
Cyclobutane
Cyclopropane

Cyclopentyne mentioned. Cyclohexene

Cyclobutene If two or more substituents are present, their
If
Cyclopropene its position
is not
ring. The
2. If only oneSubstituent is attached to the ring, Wnicn are used
ror
numbering the carbon atoms in the
i.e., 1, 2, 3, 4....et. get the lowest
l set of locants. All other
indicated by arabic numerals or anticlockwise) that the substituents get
nbering in such a way (clockwise followed. For example,
aing to n e
aliphatic or acy
cyclic compounds
are then

CH3 H3C CH
,CHCH
CH3
CHCH
3-Ethyl-1,1-dimethyleyclohexane
1-Ethyl-2-methylcyclopentane

Methyleyclopentane
 12.44
DINESH cOMPANION CHEMISTO
a
maltiple bond and some other substituents are present in the ring, the numbering is done
assign lowest number to the multiple bond. For
in such a
example,
CH3 NO2
C2Hs
CHs

2-Ethyl-3-methylcyclopent-1-ene
4.It the
ring contains lesser carbon
3-Ethylcyclopent-1-ene 3-Nitrocyclohex-1-ene
aIkane and the alkyl group attached to it, the compound is named as the deriva
atoms than the
ring is treated as cycloalkyl substituent. Otherwise, it is named as the derivative or cycloalkane. For examel
2 4 5 nple
H,C-CH2-H,-CH2-CH3 HC-H-CH-H3

2-Cyclopenty lhexane (2-Butyl) cyclohexane

5. In case, the side chain
contains a multiple bond or a functional group, the alicyclic ring is treated
irrespective of its size. For as the substite
example,
HC-H-HO CH-H-H

2-Cyclohexylpropanal 3-Cyclopropylprop-1-ene
6. If more than one alicylic rings are attached to the
single chain of carbon atoms, the compound is regarded a
cycloalkyl derivative of the alkane whatever may be the number of
carbon atoms in the
example, or the rings carbon atom chain. F

CH,-H-H--
1,3-Dicyclopropylpropane 1, 3-Dicyclohexylpropane
7. If a compound contains an alicylic ring directly attached to the benzene
For example, ring, it is named as the derivative of benze*

CH3
Cyclohexylbenzene
8, In case some functional group along with substifuents 1-(3-Methylcyclohexyl)-4-chlorobenzene
arepresent in the ring, the shoul
be done in such a way so that the functional group gets lowest
number. numbering of the carbon atoms
OH NH2
CH3
CH3 CH3
CH3
3-Methylcyclohexan-1-ol 5-Methylcyclohex-2-en-1-amine
9. In case, the functional group directly attached to
the
2,3-Dimethyleyclohex-2-en-1-one
ring contains carbon pres
such a group. atom, suitable suffixes are used to

Functional group Suffix

-CoOH
-CHO Carboxylic acid
-C=N Carbaldehyde
-COCI
Carbonitrile
-CONH2 Carbonylchloride
-COOR Carboxamide
R-Carboxylate.
 Chemistry-Some Basic Principle 12.45
echniques
are given to represent these :
A few
Pxamples
CHO CN coOC Hs

Cyclohexanecarbaldehye

Cyclohexanecarbonitrile Ethylcyclohexancarboxylate
coOH CONH2 ÇoOCHs

2-C Hs
NO2 O
3-Niocyclohex-2-ene-1-

carboxylic acid
2-Ethylcyclopentane-1
carboxamide
Ethyl-3-oxocyclohexane-1-
carboxylate
AMPLE 9

Give the 1UPAC names of the following

-CH-CH-CH=CH2 (i)
COCI

(u) (iv)
OH HC CH,CHO
CH-CH-cOCH, CH,
CHCH
(v) (vi)

CH,

(vii) 10 CH-CH-ClH-CH-CH-O
OH
OH

(ii) HC CH
CHCH

ir) 0,N
Solution.
) 4-Cyclopentylbut-1-ene
2-Hydroxycyclohexanecarbonyl chloride
4-Cyclobutylbut-3-en-2-one
4-hydroxycyclohexyl) pentane-1, 5-diol
y 4-4-Nitrocyclohexyl) benzaldehyde
AC Names of Organic Compounds represented by Bond Line Notations
cONH,
-CHO
NO,
(ii) Cyclohexylcyclohexane
(iv) 2-(2-Methylcyclobut-1-enyl) ethanal
(vi) 2-Ethyl-1, 4-dimethylcyclohexane
(vii) 2-1sopropyl-5-methyleyclohexanol
) 2-Nitrocyclohexanecarboxamide.

Bond in notation is simple, short and convenient

organic molecules. In this method
method of representing
e a

Onds are represented by lines. Thus,

a
single line )formrepresents sngle bond, two parallel lines (=) renranas

is the ot three parallel lines (=).

notation for triple bond
in
l e bond while the intersections.
the line ends or line
iy u atoms are denoted by symbols or abbreviations.
substituents are denoted by their proper
nalgroups
UpAYdrogen
or
atoms are assumed to be present in the required number in Oraer to satisty the tetravalency of carbon

UPAC n e s of some organic compounds represented by the bond line notations are given.
12.46 DINESH COMPANION CHEMIST
Bond line notation Formula IUPAC Name of the Compoum
CH3-CH=CH-CH3 But-2-ene
4 Hexa-1, 3, 5-triene
CH=CH_H=CH-CH=H2

CH3 CH3
2,3-Dimethylbuta-1, 3-diene
CH-H--u-H3 3-Ethylpenta-1, 3-diene
CzHs
CH3
CHCH-H 2, 2-Dimethylbutane
CH3
OH 4
4-Ethylhex-4-en-2-0l
CaHs OH
lCH3
H-H-Hs 2-Cyclohexylbutane
CH3
21 1
CH-CHc-CH; 2, 2-Dimethylbutane
CH
cH
CH 2-Methy1-2-cyclopropylpropane
CH
CHCH-H2-H2-H, Hex-1-yne
CH3-N-CH2-CH3
2CH-H N-Ethyl-N-methylpropan-2-amin
CH
H-H-CH-H3 3-Methylbutan-2-ol
CH, OH
OH
CH-ÉH-¢H-H2-HJ 3-Methylpent-1-ene
CH3
NH2
CHg-CH-H2-H-NH,
CH3 CH 4-Methylpentan-2-amine

O CH3
O
OH 1 2 4
CH--H2-¢-OH 4-Hydroxy-4-methylpentan-
-one

CH
Br CH-CHCH-H,-Br 1-Bromo-3-methylpentan-2-0

CH
 ChemistrySom Basic Principles& Techniques 12.47
MPLE1 0

ctructural formulae and 10PAC names

of the following compounds.
CH (ii)
o
O
NH2
(1 (iv)
0

0
(vi)

vIu) (viii)

COOH
x)
CoOH
HOOC
O

Solution. ) CsHs- H,-C-oCH Gi) H-CH,-H

Methyl-2-phenylethanoate 3-ketobutanal

CH
(ii) CH -H-NH (iv) HC-
H Butan-2, 3-dione

3, 3-Dimethylbutanamide
CH2-CH2-CH2-CH3
O
CH- H- H,- H,-H
4-Ketohexanal 1-Butylcyclopentane
CH=CH-CH3
(vii) CH=H-H,-tH-H-CH, (si) tH,-H =H-C-H=H-H,
HCc-CH3 CH=CH-CH3
1cHaene
5,6,6-Trimethylhept-1-ene 4,4-di (1-propeny)-hept-2,5-diene

(ix) CH-CH,- H-CH,-CH CH,-CH,

COOH COOH
HOOC CH,
2-Ethylhexane-1,4,6-tricarboxylic acid

6 5 4 2
) CH,-CH,-CH,-CH,-CH- CH-CH =CH,
CH,CH
4-Ethyl oct-1-ene
 12.48 DINESH COMPANION CHEMIST Organic Chemistry-Some

R
EXAMPLE 11
Write IUPAC names of the following compounds. difference
CI What is the
The molecular formul
) CH-CH-CH-C-NHCH, (i) CH3-C-CH2-C-CH3 cyclobuta
In the name

Give the IUPAC

name
Br CzH52006)
C2Hs(C.B.S.E. Can an organic compo
(C.B.S.E. 2006) 2006)
What is the IUPAC
na

In the 1UPAC namem

(ii) CH3-C=C-CH=CH-C-OH 8.
Suggest another name

Out of -CHO andc

9.
CH3 H3 Pick out the error and
(C.B.S.E. 2006 Compt.) (C.B. S.E. 2007) 10.
11. Arrange the following
(v) CHCOCH,COCH (vi) CH-CH=C-CH-CH3
CH Br 12.
Write the IUPAC nam
(C.B.S.E. 2007) (C.B.S.E. Sample Paper 2010)
(vii) CH,f =£-CH,-OH (vii) HC=CH-ÇH-CH-CH-CH
H, Br OH
13. Name the alky! groups
(C.B.S.E. 2009) (C.B.S.E. 2009)
CH
(ix) (CH)2C=CH--CH -CoOH

(C.B.S.E. Sample Paper 2010) (C.B.S.E. Sample Paper 2010)

1. CH2 2. CsHg 3. Pr
9. -CHO 10. Position of tru
CI 12. Methyl-3-chlorobut-2-en
Solution. Hy-H-ÉH2--NHCH 4
(i) CH¢- H2- -CH
Br 7C2Hs CHs Some
3-Bromo-N-methylbutanamide 3-Chloro-5-fluoro-3, 5-dimethy lheptane
Organic compounds have a
(or molecular mass) but with d
auiy CH-éac-H-u_e-oH CHy-¢H--¢H-H, in nature and
normally particip
while changing to the
H CH3 products.
product molecules are formed.
Hex-2-en-4-ynoic acid 2, 4-Dimethylpentan-3-one
discussed keeping in view the.
basis of the mechanism.
CH, H,in, i) CH- H-- H- èa, Let us first discuss the ison
CH3 Br 19. Isomerism
Pentan-2, 4-dione
4-Bromo-3-methylpent-2-ene Organic compounds. in ger
4 5
(viin CH,- -H-OH (vii) H,C = CH-CH-CH-CH,-CH
6 Two or more com
called isomers ane
CH, Br OH Isomerism has two main ty
2-Bromo-3-methylbut-2-en-1-ol Hex-1-en-3-ol. Strucural Isomerism
Space or stereoisomeris
ÇH3 Let us sudy in detail the ty
3 -coOH 20. Structural Isomeris
CH3
4-Methylpent-3-en-2-one
2-Methylcyclopent-3-enecarboxylic acid Structural isomer
Sormulae diýffering
 Chemistry-s
-Some Basic
Principles& Techniques 12.49

Very Short Answer

QuestionsS
in the
the
What is the difference molecular formula of the
two successive members in
a homologous tamily
ecular formula ot the tirst member of alkyne family is C,H,. What is the formula of the fourth memDer
The
me cyclob for a compound, what
cyclobutane
name
does cyclo represent ?
In the
Give he IUPAC name of the third member of the alkanol family.
an organic compound have two OH groups attached to the same carbon atom?
What is the IUPAC name of the compound (CH)2 NC,H; ?
UPAC name methoxyethane for
an ether, what does methoxy represent ?
another name for nitroethane.
Suggest
Out of -CHO andC= O
groups, which is preffered as principal
of functional group?
Pick out the error and write the correct IUPAC name of pent-3-yne.
Aange the following principal functional groups in order of decreasing priority
-COOH, -COOR. -OH, -CONH2, C= 0, -SO3H
Write the 10PAC name of compound

CH-C=CHCOOCH3
Name the alkyl groups which are derived from isobutane:

CH,CHCH
CH3

CH 2. CsHs 3. Primary prefix 4.

ANSWERS
Propan-1-ol 5. No 6. N-Dimethylethanamine 7. Secondary prefix 8. None
9-CHO10. Position of triple bond; pent-2-yne 11. -coOH> -So,H>-coOR> -cONH2> c=0 > -OH
12. Methyl-3-chlorobut-2-en-1-oate 13. (CH3),CHCH,- (2-Methylpropyl or isobutyl); (CH3)C- (1, 1-Dimethylpropyl or tert-buty).

Some Basic Principles in Organic Chemistry

Organic compounds have a tendency to exist as isomers. These are two or more compounds having the same molecular formula
r molecular mass) but with different physical and chemical characteristics. In addition to this, organic compounds are covalent
Taure and normally participate in the molecular reactions. Mechanism of a reaction is the path followed by the reacting species
stlechanging to the products. In other words, it explains as to how the bonds in the reacting molecules break and new bonds in the
ducl molecules are formed. In order to understand the mechanisms of organic reactions, certain concepts are involved which are
e d keeping in view the level of the students. Apart from this, the various types of organic reactions are also listed on the
Ss of the
mechanism.
Leus first discuss the isomerism in the organic compounds.
19. Isomerism
ganic compounds, in generai show, isomerism.
Two or more compounds having the same molecular formula but different physical and chemical properties are
called isomers and this phenomenon is known as isomerism.
Somerism has two main types. These are:
Structural Isomerism
Space or stereoisomerism.
shady in detail the types of isomerism associated with organic compounds.

20.Structural Isomerism
Structural isomerism is shown by the compounds having the same molecular formula but different structural
Jormulae differing in the arrangement of the atoms.
 12.50
INEBN 0OMmANN IN CREMaH
Chain or skeletal inomeriam
In this (vpe, the inomers
diTer in the
awm ohun rarbn
of carbo atoms u may de sAeden Ihey mt e r
her rNAi i n Arwn
noMed thai the rempounds roniaining wpin ihr vbH hed.h
is a continuous ehain and no d h n h t imerm
brunehing N pnnidMe li a
isoer ian by takiny veiain enaulea n aluwn n ea n
illustrate chain a nil
do nlo alhma a l t a a l al
a ati
() The olecular hnula
,l epoeta (wa ain lpa

() Three chain inmen are

poaniblo ln the muoleuua h a

CH CH, C1, , C0 '

Mutlyllua
(i) Similarly, the moleular lomua 4 ityln
uenet ve lnttt nlhne wi h liut

, , 1
Mhyl a

Metylenda ithy
Thus,
s quite evlent that as th un
it
TES
in a latge puprtims Hie (9) tha hart
can arie frrnn the mileular
funmula
e po
on Chan lmerismn in
C,01,
alkane4, In writi
hangp Fn ezatne

-1 ,

Fawit ate
fh than wmats n the

, 1, - (1, ,