1.

IUPAC NOMENCLATURE
1.1 INTRODUCTION TO ORGANIC COMPOUNDS:-
Organic compounds are compounds of carbon and hydrogen and the following elements may also be
present: (Halogens, N, S, P, O). There are large no. of organic compounds available and large no of organic
compounds are synthesized every year.The most important reason for large no of organic compounds is the
property of catenation (self

 
Element Bond Energy
C C (strongest bond)
Si Si
Ge Ge  Decreasing order
Sn Sn
Pb Pb
Bond energy depends on
(i) Size of atom (Inversely proportional) Size : C
(ii) E.N difference along period (Directly) E.N Diff : C 













(iii) Bond order (no. of covalet bonds b/w two atoms) (Directly) Bond order : C 






  C
Catenation in carbon:-
 The element carbon has strongest tendency to show catenation or self



(a) its tetravalency so that it can form  bonds with many elements as well as carbon itself.
(b) It can form multiple bonds (C = C, C  C). Due to its small size, there is efficient colateral overlapping
b/w two P 

Does not exist

(c) High bond energy of C 






!







"
!#

Hybridised of carbon :
It is of three types and these are sp3, sp2 and sp. These hybridised state in any given structure can be
known by counting  bond around the carbon atoms as  bond are formed by hybrid orbitals. Thus if there
are four  bonds, three  bonds and two  bonds around the carbon atom then C atom will be in sp3,
sp2 or sp hybridised state respectively.

page # 2
 Few informations regarding these orbitals are summarised as

C
 1.54 1.34 1.20
length (A$
C
 1.10 1.07 1.06
length (A$

C
 80%& 142 200
energy
(Kcal/mole)

C
 98.6 106 121
energy
(Kcal/mole)
Since the extent of overlap in sideways overlap is low, a carbon 
 

'"
'

a carbon 
 
(
  
 

)
'*)



  

bond since it consists  


'
 
+

!
'")

  
#



stronger than carbon 
 



  
  
   
  
(i) How many  &  bonds are present.
(ii) How many type of hybridised carbon atoms are present.
(iii) Which orbitals are used in marked C

(iv) Total number of unhybrid orbitals over the C-atom.

Ex. Give the answer of all the four parts for CH2= C *  C
* H C

(i) 7 and 3
(ii) sp2 and sp
(iii) for (sp2 
#
2
(iv) 6 (as sp hybridised C-atom has one unhybrid orbital and sp hybridised C-atom has two unhybrid
orbitals)

Que. Evaluate yourself by answering above four questions for the following structures :

(a) (b) (c)

(d) (e) (f)

1.2 IMPORTANT TERMS:

Saturated compounds:
When all the valencies of an element are satisfied by  covalent bonds.
Unsaturated compound:
When a compound contains one or more  bonds (C = C, C = N, N = N, C = O or C  C, C  N, N  N)
Molecular Formula (M.F.) :
The molecular formula of a compound indicates the actual number of atoms of each element present in one
molecule.

page # 3
Structural Formula (S.F.):
It indicates the linkage due to covalent bond between different atoms in a molecule.
(i) Expanded Structural Formula (E.S.F.)
(ii) Condensed Structural Formula (C.S.F.)
(iii) Bondline Structural Formula (B.S.F.)
Ex. M.F. C3H8 Ex. M.F. C4H10
H H H H H H H
E.S.F. H 






 E.S.F. H 









H H H H H H H
C.S.F. CH3 
2 
3 C.S.F. CH3 
2 
2 
3

B.S.F. or B.S.F.

Ex. B.S.F. Ex. B.S.F.

CH 3 


 2

 3
C.S.F. M.F. C6H12
CH3
M.F. C5H12
Homologous series :
Homologous series may be defined as a series of similarly constituted compounds in which the members
possess the same functional group, have similar chemical characteristics and have a regular gradation in
their physical properties. The two consecutive members differ in their molecular formula by CH2.

Degree of carbon :
It is defined as the number of carbon atoms attached to a carbon atom.
H
|
Primary (1,
 

-
Secondary (2,
 

| 1,
H

C C
| |
Tertiary (3,
 

-
Quaternary (4,
 

| | 4,
3,
H C

Superprimary : (1,

0
1 
&
 
CH3 CH3 20 
.
 
1 2 | 3| 4 5
CH3 




2

3
Ex. | 30 
.
 
CH3
0
4 
.
 

Ex.

page # 4
 *Degree of hydrogen is same as the degree of carbon to which it is attached.
Type of C 


/
"#

# 
0!


" 
Note : Total no. of monosubstituted product does not depend upon type of C-atoms but depends upon type
of replaceable H-atoms.
1$
C H3
1$ | 2$ 3$ 1$

Ex. C H3  4 $ C  C H 2  C H  C H3
| |
C H3 C H3
1$ 1$

Que. Mark the type of C-atoms present in the following structure :

(a) (CH3)3C13)3 (b) (c) (C2H5)4C (d) (e) (f)

Ex. Write the structure of alkane (MM = 72) having 1$)

2$

3$
 
!
CnH2n+2 = 72
CnH2n = 72 
2

45
12n + 2n = 14n = 70
n = 70/14 = 5
Thus molecular formula is C5H12 and structure will be like

1.3 CLASSIFICATION OF ORGANIC COMPOUNDS :

Ex. Compounds Classification

Unsaturated

Heterocyclic , saturated

Unsaturated

Saturated

Saturated, Alicylic

page # 5
Aromatic Compound [The Huckel (4n + 2) rule] :
The following three rules are useful in predicting whether a particular compound is aromatic or non!
1. Aromatic compounds are cyclic and planar.
2. Each atom in an aromatic ring is sp2 or sp hybridised and has close conjugation.
3. The cyclic  molecular orbital (formed by overlap of p-orbitals) must contain (4n + 2) electrons,
i.e., 2, 6, 10, 14 ........  electrons. Where n = an integer 0, 1, 2, 3,..............

Non-Benzenoid:
H H



 + Cation 2 e Cyclopropenium ion


H H


+
 Cation 2 e Cyclobutenium dication
+


H H

H H


 Anion 6 e Cyclopentadienyl anion

..



H - H


H H



H H


 6 e


Cycloheptatrienyl cation (Tropylium cation)

+


H H



Benzenoid Aromatic Compounds:

All organic compounds which contain atleast one benzene ring are known as benzenoid aromatic com-
pounds.

Spiro Compounds: One atom shared by two rings

Fused Bicyclic Compounds: Two adjacent atoms shared by two rings

Bridged Bicyclic Compounds:More than two atoms shared by two rings

Isolated Bicyclic Compounds:Two rings directly attached by a sigma bond

1.4 IUPAC NOMENCLATURE OF ORGANIC COMPOUNDS:

General Scheme of Naming:-
Secondary prefix + Primary prefix + Word root + Primary suffix + Secondary suffix

(1) Word Root : It indicates the no. of carbon atoms present in the main chain (parent chain). It is
represented as Alk.

page # 6
 (2) Primary Suffix:- It indicates the saturation or unsaturation existing in the main chain.
ane  single bond (saturated)
ene  one = bond
diene  If two double bonds
Polyene  if plenty of double bond are present.
yne  one  bond
diyne  two  bond

(3) Secondary Suffix:- It is used for the principal functional group.

(4) Primary Prefix : "

'



"
!#

(5) Secondary Prefix : Normal substitutents and junior functional groups are treated as a substituent,
then their name is treated as secondary prefix.
The following substituent groups are always cited in the prefix.
(i) 6 Alkyl
(ii) 6 Alkoxy
(iii) 7 halo (fluoro, chloro, bromo, iodo)
(iv) 2 Nitro
(v) 

 Nitroso
(vi) Junior functional groups.
 The prefixes are always written in alphabetical order
 The position of substituent group in the main carbon chain is mentioned by writing the number just
before the name of substituent by writing a hyphen ( 

1.5 NAMING OF SATURATED HYDROCARBONS

Rules :(Branched and substituted Alkanes)
Selection of parent chain :
(a) Chain with maximum number of 
!
1
 

(b) If number of carbon atoms are same in more than one longest chain then more substituted longest chain
will be the parent chain.

(c) If number of side chain are also same then that will be parent chain having its substituent at lower number.
C C
C 














C 



C
Numbering :
(a) Numbering is done from that side of the parent chain having it substituent at lower number
(lowest set of locant)

page # 7
(b) If position of substituent are same from both the end of the parent chain, then numbering is done
from alphbetical order.

* If alphabets are also same then numbering is done from that side of the parent chain having its
substituent of substituent at lower number.

CH3


Ex. CH3 


3 Methylpropane

CH3 CH3


CH3 




3 2, 3-Dimethyl butane

CH3
 

CH3 


3 Dimethyl propane
CH3

2-Methylbutane

C


C 






 3-Ethyl-2-methyl hexane


C 




C 



 

C 






 4, 4-Diethyl heptane
C 




C
  

C 



C 






 4, 4-Diethyl-2, 5-Dimethyl heptane
C 





C 






 3-Ethyl hexane


C 



CH3 
2 
2 
2Cl 1-Chlorobutane

C 






 3-Bromo-2-chloropentane



Cl Br

C 






 2-Bromo-4-chloro pentane


Cl Br

Cl
 

C 






 4-Bromo-2, 2-dichloro pentane


Cl Br

C 








 5-Bromo-2, 3-dichloro hexane



Cl Cl Br

page # 8
Rules for writing Radicals :

Alkane Alkyl

Alkene Alkenyl

Alkyne Alkynyl

Benzene Phenyl
H
CnH2n + 2  CnH2n + 1 Alkyl Radical
H
CnH2n  CnH2n 
. Alkenyl Radical
H
CnH2n 
2  CnH2n 
3 Alkynyl Radical

H
 Phenyl

R (structural formula) Name

CH3  Methyl
CH3 
2  Ethyl

CH3

 3 2| 1
CH3 


2 

+ "
CH3 |
| H
(b) CH3 


3
| CH3
H |

 CH3 


3 Tert butyl
| (Tertiary butyl)

CH2 = CH2 CH2 = CH 

ethenyl
CH3 


2 Prop 
.

"

Methylethenyl

Prop 
2

"

CH3 

 CH CH3 

 C 
Prop-1-ynyl

CH3 

 CH 
2 

 CH
Prop-2-ynyl

page # 9
Benzene Radical :

1. Phenyl

2. Benzyl

3. Benzal

4. Benzo

5. Tolyl

CH3
(o, m, p)

 Methylene

7. Alkylidene

8. - naphthyl

9. -naphthyl

Systematic Names of Radicals :

Complex Radical :

Ex 5 

1
.)2

8!"##"


5 
1.).

8!"##"


page # 10
 5 
1.

9"##"


5 
18!""


Numeral Prefixes :
(1) Following prefixes are considered for alphabetization :

(a) Iso

(b) neo

(c) Di, Tri, Tetra of complex radical are considered for alphabetization

(2) Following are not considered for alphabetization

(a) Di, Tri, Tetra for simple radicals.
(b) Sec, Tert are not considered for alphabetization
(c) Bis , Tris

Retained Names of Alkanes:

(1) Normal (n) : Radical or hydrocarbon which has straight chain and if it has free valency it must be present
at either of ends.
C  (n butane)

page # 11
 (2) Iso : Two methyl group at the end of linear chain (unbranched chain)
C


(i) C 
C 
 Isobutane or methyl propane


(ii) C 
C 


 Isopentane or methylbutane


(iii) C 
C 




 Isohexane or 2-methylpentane
Conditions :-
 There should be 4 to 6 carbon atoms only
 There should not be any other alkyl group present in the chain.
Q. Iso-octane (commercial name) in petroleum industry
C
 

Ans. C 
C 


C 
 IUPAC name is 2, 2, 4-trimethylpentane


C C

(3) Neo :  There should be 5 to 6 carbon atoms

 2, 2-dimethyl
 No other substituent.
C
 

Ex. C 
C 
 Neopentane
C
C
 

C 
C 


 Neohexane
C
(4) Secondary : It is applicable only for radical.

Ex.1

(5) Tertiary :

First member

1.6 NAMING OF UNSATURATED COMPOUND (ALKENES AND ALKYNES) :

(A) General formula:- CnH2n and CnH2n 
2 respectively

(B) Rules for selection of main chain:-

 Longest carbon chain with a multiple bond.
 Longest carbon chain with maximum number of multiple bonds.
 If first and second factor are common then chain with lowest locant (multiple bond) is selected as main
chain.
 Lowest locant Rule is followed till first point of difference. (Multiple bond prior to substituent).
 Alphabetization.
(C) Rules for Numbering:-
 Lowest locant Rule till first point of difference (irrespective of double bond or triple bond).
 Then double bond is prefer over triple bond in numbering, naming and longest chain selection, If all the
other factors are common

page # 12
 Ex. CH3 
2 


2 But-1-ene
CH3 




3 But-2-ene

CH3
4-Methylpent-1-ene


CH3 


2



2
CH3
|
CH3 






3 4-Methylpent-2-ene
Cl

 
6 5 4 3 2 1
CH3 


2

2



2 5, 5-Dichlorohex-1-ene
Cl
(a) C = C 


 Buta-1,3-diene

(b) C  C 

 C Butadiyne

(c) C = C 

 C Butenyne

C  C 






 Hex-4-en-1-yne
1 2 3 4 5 6

Ex.1 3-(2-Methylpropyl) hept-1-ene

Ex.2 4 -(1,1-Dimethylpropyl)-4-ethenylhepta-1,5-diene

Ex.3 3-Ethynylhexa-1, 5-diene

Ex.4 4-Ethenylhept-2-en-5-yne

Ex.5 4-(1, 2-Dimethylbutyl) hept-2-en-5-yne

Ex.6 2, 4-Dimethylpenta-1, 3-diene

Ex.6 2,3-Dimethylhex-1-en-4-yne

page # 13
1.7 NAMING OF CYCLIC HYDROCARBON (ALICYCLIC COMPOUNDS) :
(A) Main chain selection:
(a) Multiple Bond > No. of carbon atoms > Maximum no. of substituents > Nearest locant > Alphabetization.
(b) If all factors are similar in cyclic and acyclic part, then Cyclic > Acyclic
(B) Numbering:
(a) Lowest Locant (b) Alphabetization
(C) Naming:
 Prefix "


:
 

'





!

 If cyclic part is the main chain then the prefix "




# 
.
If cyclic part constitutes the side-chain (substituent) then prefix cyclo is considered for alphabetization:-

Ex:- Cyclopropane Cyclobutane

Cyclopentane Cyclohexane

Cycloheptane Cyclooctane


Methylcyclopropane Ethylcyclopropane

Propylcyclopropane 1-Cyclopropylbutane

C 


 Cl 





2-Chloroethylcyclopropane Chloroethylcyclopropane

Cl Cl


 

C 


 C 



3 2 1 1-Chloro-3-cyclopropylpropane 1 2 3 1-Chloro-1-cyclopropylpropane


Cl
Br


C 


 1


 

1-Chloro-2-propylcyclopropane 4
3
F 2-Bromo-1-chloro-3-fluoro-4-iodocyclohexane


Cl


Methylethylcyclopropane or isopropylcyclopropane

Cl
Br


2


3 1
4 6
1-Bromo-2-chloro-4-iodocyclohexane
5


6 6 Br
1 5 1 5
2 4 2
3 3-Chlorocyclohex-1-ene 3
4 5-Bromo-3-chlorocyclohex-1-ene
Cl Cl

page # 14
1.8 FUNCTIONAL GROUP TABLE (Seniority order):

Class Name Suffix Prefix

1. R 
 Alkanoic acid 



1 <"
 Carboxy

2. R 
3H Alkane sulphonic acid  sulphonic acid sulpho

3. R 






6 Alkanoic anhydride 
" ------------
|| || (carboxylic anhydride)
O O

4. R 
6 Alkyl alkanoate 

(carboxylate) Alkoxy carbonyl

5. R 


7
Alkanoyl halide 
"

1 "
halide) halo carbonyl
||
O

6. R 


2
Alkanamide 
!
1 <! Carbamoyl
||
O

Alkanenitrile 

1  cyano
7. R 

 N

8. R 



Alkanal 

1 " formyl / Oxo
||
O

9. R 


6 Alkanone 
 Oxo / Keto
||
O

10. R 
 Alkanol 
 hydroxy


 mercapto
11. R 
 Alkanethiol


! amino
12. R 
2 Alkanamine

1.9 NAMING OF FUNCTIONAL GROUP CONTAINING COMPOUNDS :

Selection of Main Chain:
Senior F.G. > Max. no. of F.G. (Similar group) > Multiple bond > Max. no. of 
!

;<



> lowest locant > alphabetization
Numbering (See F.G. + Sub.):
The carbon atom bearing functional group (or C 
!

!

#

*
'
# 
number.
(i) Lowest locant (F.G. > M.B. > substituent > Alphab)
Naming:- General scheme :
The senior most functional group constitutes secondary suffix. Other junior F.G.

'

# <

alphabetical order.
(A) Rules for non chain terminating functional groups
(3H, >CO,   2 etc.)
Rule : (1) Parent chain selection :
Select the longest possible chain with maximum functional groups and maximum unsaturation.
4 3 2
CH3 
2



2

3
|
1
CH2OH

page # 15
 Rule : (2) Numbering :
Numbering is done from that side of the chain which gives lowest locant to the principal functional group
followed by double and triple bonds.

O O
6 5 4 3|| 2 1 1 2 3 4|| 5 6
CH3 


2



2

3 CH3 


2



2

3
| |
CH3 (I) correct CH3 (II) wrong

( C = O group gets lowest number 3) ( C = O group gets number 4 which is not lowest)

(B) Rules for chain terminating functional groups :

(        2,  
    N etc.)

Rule : (1) When a chain terminating principal functional group is present in the carbon chain, it is always
given number 1 (one.)

3 4 5
CH3  CH2  CH  CH2  CH  CH3
1
| | 7
2 6
CN  CH2 CH2  CH3

Rule : (2) If a compound contains two or more like groups, the numerical prefixes di, tri, tetra etc. are
used

CH2  CH  CH2
| | |
OH OH OH

Rule : (3) The name for benzene as substituent is phenyl. In case the phenyl ring is further substitued,
the carbon atom of the ring directly attached to the parent chain in such a ways that the substituent on
the ring gets the least possible number. For example

(C) IUPAC name of polyfunctional compounds :

Rule : (1) When an organic compound contains two or more different functional groups then senior
functional group is selected as the principal functional group while other groups are treated as substituents.
Rule : (2) Some functional group such as halo groups (fluoro, bromo, chloro, iodo), nitroso (NO) nitro (
NO2) and alkoxy (6

'"


 
#

1.9.1 Sulphonic acid

F.G. Prefix Suffix IUPAC name


3H Sulpho Sulphonic acid Alkanes sulphonic acid

page # 16
 Ex. (1) CH3 
3H Methanesulphonic acid

(2) C 






 Pentane-2-sulphonic acid


SO3H
SO3H


(3) Cyclobutanesulphonic acid

1 2 3 4 5
(4) HOOC 








 3 5-Sulphopentanoic acid

1.9.2 Ketone:-

F.Group Prefix Suffix Name



C=O Keto or oxo one Alkanone



Example:- (1) CH3 

C 
3 Propanone
O
O

(2) Cyclohexanone

(3) Cyclohexane-1, 3, 5-trione

O O
O
CH2 


3


(4) 2-(2-Oxopropyl) cyclohexanone

O

COOH


(5) 3-(3-Oxobutyl) cyclohexane -1-carboxylic acid



CH2 
2



3
O

1.9.3 Alcohol:-

F.Group Prefix Suffix Name

OH Hydroxy ol Alkanol

Example:- (1) CH3 



2

 2-Methyl Propanol


CH3

(2) CH 3 


 2

 2



 3 2, 5-Dimethylhexane-1, 6-diol


CH 2 
 CH 2 
OH

OH


HO OH


(3) Cyclohexane-1, 2, 3, 4, 5, 6-hexaol




HO OH


OH

page # 17
 OH


Cl 
2



2


(4) CH 
2

2

2

2




CH3 
2

2



Cl OH
7-Chloro-5-(3-Chloro-2-hydroxy propyl) octane-1, 6-diol
O
HO OH



(5) 2, 4, 6-trihydroxy cyclohexane-1, 3, 5-trione
O O


OH

(6) CH2 


CH2 (Glycerol) Propane-1, 2, 3-triol





OH OH OH
1.9.4 Thiol:-

Ex. (1) CH3 

 Methanethiol

(2) Butane-2-thiol

(3) Cyclobutanethiol

(4) 3-Mercaptobutan-2-ol

1.9.5 Amines:-

F.Group Prefix Suffix Name

2 amino amine Alkan amine

(a) R 
2 1$

! Alkanamine

(b) R 


6= 2$

! N  Alkylalkan a min e
H (R' ) (R )

(c) R 


6= 3$

! N, N-Dialkylalkanamine
R'

(d) R 


3 N-Ethyl-N-methylalkanamine
CH2 
3

Ex:- (1) CH3 

2 Methanamine

(2) C 






 Pentan-3-amine


NH2
(3) C 
 






 N-Ethylpropan-1-amine

(4) C 






 N-Ethyl-N-methylpropan-1-amine


C
C
page # 18
 (5) C 


 N-Ethylpropan-2-amine


NH    

OH


(6) CH2 






3 4-(N-Ethyl amino) pent-2-en-1-ol


NH 
2

3

1.9.6 ETHERS (R  

F.Group Prefix Suffix Name

R 


6= alkoxy  Alkoxy alkane

Alkoxy + Alkane
 
less no. more no.
of ' C' of ' C'

(i) Acyclic Ethers:-

(1) C 


 Methoxymethane

(2) C 




 Methoxyethane

(3) C 






 1-Methoxypropane

(4) C 
C 
 2-Methoxypropane


O


C
C


(5) C 






C 
 1-Isopropoxypropane
1-(Methylethoxy) propane

O 





(6) Ethoxycyclohexane

O


(7) Cyclopropoxycyclohexane

Br


3 O 







4 2
(8) 5 1
3-Bromo-6-chloro-2-propoxycyclohexan-1-ol
6
OH



Cl
 In cyclic system, numbering always starts from senior most functional group.
OH


1 Br


2
6
(9) 6-Bromo-5-methoxycyclohex-2-en-1-ol
3 5


4 O 
3

OH


1 Br


2
6
(10) 6-Bromo-5-ethoxycyclohex-3-en-1-ol
3 5
O 





page # 19
 (ii) Cyclic Ether :
Hetero cyclic compounds
(1) C 
 Oxirane or Epoxyethane
O

(2) C 


 1, 3-Epoxypropane
O

(3) C 


 1, 2-Epoxypropane
O
Cl


(4) C 


 1-Chloro-2, 3-Epoxypropane
O

1.9.7 Hetero atom containing compound :

If hetero atom





!


#


"

'

(1) 
 Aza
(2) 
 Oxa
(3) 
 Thia
(4) 
 Selena

Example:- (1) HOOC 

2 


2 
3 3-Aza pentanoic acid

H


N
(2) Aza Cyclo pentane

H


N
(3) 3-Methyl aza cyclo hexane


CH3
 Polyethers:-
(1) C 




C 
 





1 2
1, 2-Diethoxyethane
1 2 3 4 5 6 7 8 9 10 11
(2) C 



















3, 6, 9-Trioxaundecane
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
(3) C 



























2, 6, 9, 13-Tetraoxapentadecane

2 3
1 4
O O 5
12
(4)
11 6
O
10 O7
9 8

1, 4, 7, 10-Tetraoxacyclododecane

1.9.8 Carboxylic acid

F.G. Prefix Suffix IUPAC name
Oic acid - 'C' of COOH considered
Alkanoic acid
in the parent chain

 Carboxy
Carboxylic acid - 'C' of COOH is not
Alkane carboxylic acid
considerd in parent chain

Rule : If first alphabet of sec. suffix is begin from a, i, o, u, y then 


#!"
 <
'

##

page # 20
 Ex. (1) HCOOH Methanoic Acid
(2) CH3 
 Ethanoic Acid

(3) C 


 Propanoic Acid

(4) C 




 Butanoic Acid

2 3 4 5 6
(5) C 












 2-propylhexanoic acid
1
COOH

COOH


(6) Cyclopropanecarboxylic acid

2 1
CH2 



(7) Cyclopropylethanoic acid

COOH


1' 2'3'
C 




(8) 4-(2-carboxypropyl) cyclohexane-1-carboxylic acid



COOH

(9) HOOC 
 Ethanedioic acid

(10) HOOC 
2 
 Propanedioic acid
(11) HOOC 
2 
2 
2 
2 
 Hexanedioic acid

(12) Cycloprop-1-ene-1, 2, 3-tricarboxylic acid

1.9.9 Acid halide:-

F.Group Prefix Suffix Name




7 Halo Carbonyl Oyl-halide Alkanoyl halide
O or or
Carbonylhalide Alkane carbonyl halide

O = C 



Example:- (1) Benzene carbonyl chloride

(2) CH3 
C 
 Ethanoyl chloride
O
(3) Prop-2-enoyl bromide

(4) 6-Methyl hept-4-en-2-ynoyl chloride

page # 21
 Cl O


C


(5) CH2 
2

2





 5, 5-Dichlorocarbonylpentanoic acid


COOH O

COOH


(6) 3-Chlorocarbonyl cyclopropane-1, 2-dicarboxlic acid


C 



COOH
O

O
(7)  C 
2







 2

 5-Methylhept-3-ene-1, 7-dioyl Chloride
Cl


CH 3

(8)

4-Bromocarbonyl-2-chlorocarbonyl-5-propanoyloxycycloexane-1-carboxylic acid

1.9.10 Nitrile:-

Example:- (1) H 
 Methanenitrile

(2) CH3 
 Ethanenitrile

(3) CH3 


2

 3-Methyl butanenitrile


CH3

CN


(4) Cyclopropane-1, 2, 3-tricarbonitrile

CN


CN


CN


(5) Benzene carbonitrile

CH2 
2


(6) 3-Cyano propanoic acid


CN

CH2 


CH2
(7) Propane-1,2,3-tricarbonitrile





CN CN CN

page # 22
1.9.11 Isocyanide :-

F.Group Prefix Suffix Name




 Isocyano Isocyanide Alkyl Isocyanide

Example:- (1) CH3 


 C Methyl isocyanide

(2) CH3 
2 

 C Ethyl isocyanide

NC


(3) Phenyl isocyanide

1.9.12 Aldehyde:-

F.Group Prefix Suffix Name

CH = O Formyl or oxo al or carbaldehyde Alkanal or Alkane

Carbaldehyde

Example:- (1) HCHO Methanal

(2) CH3 
2 


 Propanal

(3) CCl3 
2 
2 
2 


 5, 5, 5-Trichloro pentanal

CH = O


(4) Cyclohexane carbaldehyde

CH = O


(5) Benzaldehyde/Benzene carbaldehyde

Ph CH = O



(6) CH 
 2-Chloromethyl-3, 3-diphenyl propanal
Ph 


CH2Cl

CH = O


(7) Benzene-1, 3-dicarbaldehyde



CH = O
(8) HOOC 
2 
2 
2 


 5-Oxopentanoic acid

(9) HOOC 
2



2

 3-(2-Oxoethyl) pentane-1, 5-dioic acid


CH2 




COOC2H5


(10) ` Ethyl 3-(3-oxopropyl) cyclohexane-1- carboxylate



CH2
2





page # 23
 (11) OHC 
2



2

3 3-(N-Phenyl amino) pentanal


NH 


(12) CHO (Glyceraldehyde) 2, 3-Dihydroxy propanal

 
CH 

CH2 


(13) OHC 
2 
C 
3 3-Oxobutanal
O
1.9.13 Anhydride

Heat
(a) R 





>






6
 R 
C 


C 
6
H2O
O O O O
Alkanoic anhydride
(b) Mixed Anhydride (according to alphabet)
CH3  COOH + CH3  CH2  COOH  CH3 
C 


C 
2H5
Ethanoic Pr opanoic
Acid O O
acid
Ethanoic propanoic anhydride

Ex. (1) H 
C 


C 
 Methanoic Anhydride
(unstable )
O O

C C
C 











(2) 2-Methylpropanoic anhydride
O O

(3) Butanedioic anhydride

(4) C 














 Butanoic anhydride
|| ||
O O

O
||
C
(5) O Cyclohexane-1, 2-dicarboxylic anhydride
C
||
O

(6) 





 Cyclopropane carboxylic anhydride
O O

page # 24
 (7) Benzene dicarboxylic anhydride (Phthalic anhydride)

1.9.14 Ester :
F.group Prefix Suffix Name


C 
6 Alkoxy Carbonyl Oate Alkyl....alkanoate
O
or or or
(Ester) Alkanoyloxy carboxylate Alkyl.....Alkanecarboxylate

H2 O R 




6=
R 





>




6= 
O
O

Example:- (1) H 
C 


3 Methyl methanoate
O
(2) C 


C 






 Propyl propanoate
O
(3) C 




C 




 Ethyl butanoate
O
C


(4) C 
C 




C 
 Isobutyl methanoate
O
3 2 1
(5) C 








 3-(Methoxycarbonyl)propanoic acid
O
(6) C 
C 






 3-(Ethanoyloxy)propanoic acid
O

(7)

2-(Methoxycarbonyl)-4-(Propanoyloxy) cyclohexan-1-carboxylic acid

O
C



O
(8) Cyclopropyl benzene carboxylate

O
(9) 




2

3 Methyl-3-propanoyloxy cyclohexane carboxylate

O=C


OCH3

page # 25
1.9.15 Amide:-

F.Group Prefix Suffix Name




2 Carbamoyl amide Alkanamide
O or or
Carboxamide Alkane Carboxamide

Example:- (1) H 
C 
2 Methanamide (Formamide)
O
(2) CH3 
C 
2 Ethanamide (Acetamide)
O
(3) CH3 
C 


3 N-methylethanamide
O

(4) CH3 








 N-butyl-N-propylethanamide


O C
C
C
C

O = C 
2


(5) Benzene carboxamide

O = C 
2


(6) Benzene-1, 3-dicarboxamide



C 
2
O

COOH


(7) 3-Carbamoyl cyclohexane-1- carboxylic acid



C 
2
O

O
C 


3
(8) CH2 N, N08!"
##0.)
30!
C 


3

O
1.10 AROMATIC COMPOUNDS:

CH3


(1) Methylbenzene (Toluene)

CH3


CH3


(2) (Ortho) 1, 2-Dimethylbenzene (Ortho-xylene)

page # 26
 CH3


(3) (Meta) 1, 3-Dimethylbenzene (Meta-xylene)


CH3
CH3


(4) (Para) 1, 4-Dimethylbenzene (Para-xylene)


CH3

Q. Write structures of the following

C 



(i) Metadiethylbenzene
C 



C 



(ii) 1-ethyl-4-isopropylbenzene


C 




(iii) Orthodiethenylbenzene
C=C



C=C
Trialkyl Substituted Benzene:
If all the three substituents are similar, then only 3 trisubstituted benzene derivative are possible.
C C
C






C



C

C


C


C
1, 2, 3-Trimethyl benzene 1, 2, 4-Trimethyl benzene 1, 3, 5-Trimethyl benzene
(Vicinal Trimethyl benzene) (Unsymmetrical Trimethyl benzene) (Symmetrical Trimethyl benzene)

Examples :

1. Isopropylbenzene (Cumene)
 

C 

C
C


2. 1-Chloro-4-methyl-2-nitrobenzene


NO2


Cl
C=C
3. Phenylethene (Double bond > Phenyl) (Common name : Styrene)

C 





4. 3-Phenylprop-1-ene (Allylbenzene)

CH = CH 
3


5. 1-Phenylprop-1-ene

page # 27
 COOH


6. Benzene carboxylic acid (Benzoic acid)

O O
C 





7. Benzene carboxylic anhydride (Benzoic anhydride)

SO3H


8. Benzene sulphonic acid

O
C 


25


9. Ethyl benzene carboxylate (Ethyl Benzoate)

O 


3


10. O Phenyl ethanoate

O
C 



11. Benzene carbonyl chloride  Benzoyl chloride

O
NH 


3


12. N-Phenylethanamide

O
C 


3


13. N-Methylbenzene carboxamide

CN


14. Benzene carbonitrile (Benzonitrile 

##

CH = O


15. Benzene carbaldehyde (Benzaldehyde 

##

O
C


16. Diphenyl ketone (Benzophenone)



O
C


17. Methyl phenyl ketone (Acetophenone)



CH3

OH


18. Phenol

OH


19. 
3 Methylphenol [o-Cresol, m-cresol, p-cresol]

page # 28
 OH


OH

20. o-Hydroxyphenol (Catechol)

OH

21. m-Hydroxyphenol (Resorcinol)
 OH
OH


22. p-Hydroxyphenol (Quinol)(Hydroquinone)



OH
NH2


23. Benzenamine (Aniline)

SH


24. Benzenethiol

O
O 


CH3
O
25. 




 2-Ethanoyloxy (Acetoxy) benzene -1-carboxylic acid (Aspirin)

1.11 Calculation of Degree of Unsaturation (DU):-

(a) It is the hydrogen deficiency index (HDI) or Double Bond Equivalence (DBE)

2H 2H
(b) H3 C  H2C  CH3   CH3 

 CH or CH2 = C = CH2 or
(DU  O)

That means Deficieny of 2H is equivalent to 1 DU

(c) (i) 1DU = Presence of 1 Double Bond or Presence of 1 Ring closure
(ii) 2DU = Presence of 2 Double bond or 1 Triple bond or two ring closure or 1 double bond + 1 ring.
(d) G.F. D.U.
y
(i) CxHy (x + 1) 
 
2

yo
(ii) CxHyOz (x + 1) 
 
 2 

ys
(iii) CxHyXs (x + 1) 
 
 2 

yw
(iv) CxHyNw (x + 1) 
 
 2 

ys w
(v) CxHyOzXsNw (x + 1) 
 
 2 

page # 29
Ex Calculate DU of following compounds

(a) C6H6O DU = 4

(b) C6H5Cl DU = 4

(c) C6Br6 DU = 4

(d) C5H11OCl DU = 0

(e) C9H12N2 DU = 5

(f) C6N6 DU = 10

(g) C10H8SO5 N4Cl2 DU = 8

e.g. M.F. DU S.F.
H H
C
1. C4H6 2 H H
H H
C 



 C

C 

 C 


C = C 



C

CH2

2. C2H2Cl2 =1

Total isomers = 3

3. C7H6O (Aromatic) =5

4. C7H8 (Aromatic) =4

Note : In case of the aromatic Compounds minimum DU = ?

@
!


.
AB


present

page # 30