Chemistry

Nomenclature of
Organic Compounds
Lets Fall In Love with Chemistry
 LECTURE – 1
IUPAC Nomenclature of Hydrocarbons
 Nomenclature of Organic Compounds
Organic Chemistry - Chemistry of ‘C’ and its compounds

Ground state of ‘C’ 1s 2 | 2 = unpaired es present here

2s 2p

1st excited state of ‘C’ 1s2 |

4 = unpaired es
2s 2p

C Tetravalency of 'C'
Classification of Organic Compounds
ORGANIC COMPOUNDS

Open chain Compounds Closed chain or Cyclic or

or Acyclic Compounds Ring compounds

HOMOCYCLIC HETEROCYCLIC
Saturated Unsaturated Other functional
organic organic group containing In a ring all In a ring other than
compounds compounds organic are carbon ‘C’ atoms like N, O,
compounds atoms S etc. are also
present with ‘C’
ALKANES ALKENES ALKYNES
ALICYCLIC AROMATIC

ALICYCLIC AROMATIC
Open chain or Acyclic organic compounds
Carbon compounds with straight C-chain or with branches of C-
Saturated organic compounds
Those organic compounds in which always  bonds (covalent bonds) present between
C-atoms .
Example ALKANE or Alk + ane

It represents no. Primary p

NOTE: of C-atoms in a Suffix
For single covalent bond given compound
P Suffix - ane (Also known as word It represents
For double covalent bond root) type of bond
P Suffix - ene between C-atoms
For triple covalent bond
P Suffix - yne
No. of C-atoms & their used alk.

No. of C-atoms Alk No. of C-atoms Alk

1C - Meth 11C - Undec
2C - Eth 12C - Dodec
3C - Prop 13C - Tridec
4C - But 14C - Tetradec
5C - Pent 15C - Pentadec
6C - Hex 16C - Hexadec
7C - Hept 17C - Heptadec
8C - Oct 18C - Octadec
9C - Non 19C - Nonadec
10C - Dec 20C - Eicos
Alkane with 20 C-atoms - C20H42 (Eicosane)
100 C - Hect
Alkane with 100 C-atoms - C100 H202 (Hectane)

Alkane family (Alkane is the IUPAC name of alkane family)

Gen. formula C n H 2n +2
Here n = no. of C-atoms
Simplest alkane
• Methane (n=1) [CH4 ] closed structure
H 4  + O  = sp3
• Open chain structure |
H−C−H
|
H 4 B.P. + O l.p. = 4 = sp3
Next homologous Butane (n=4)
Two consecutive members of same family in  molecular formula  C4 H10
which difference of –CH2- group (methylene or
CH2 = ) is present.
Closed structure → CH 3 − CH 2 − CH 2 − CH 3 or
Ethane (n=2)  molecular formula → C2H6
Closed structure → CH3 – CH3 H 3C − (CH 2 ) 2 − CH 3
or
H H H H H H
Open chain structure → H − C − C − H Open chain structure H−C−C−C−C−H
H H H H H H
And similarly,
Propane (n=3)  molecular formula → C3H8
Heptane (n=7)  molecular formula  C7 H16
Closed structure → CH 3 − CH 2 − CH 3 H H H H H H H
H H H H−C−C−C−C−C−C−C−H
Open chain structure →
H−C−C−C−H H H H H H H H
H H H H 3C − (CH 2 )5 − CH 3
Decane (n=10) (Molecular formula  C10 H 22 )
H H H H H H H H H H
H−C−C−C−C−C−C−C−C−C−C−H
H H H H H H H H H H
Alkyl Radicals (or Alkyl Groups)
When we subtract one H-atom from any member of alkane family then one valency of
C-atom is totally free and that group is known as alkyl group (or Alkyl Radical)
Alkane Alkyl Group (R −)
Gen.formula Gen. formula
−H
⎯⎯ →
Cn H 2n +2 Cn H 2n +2−1 or Cn H 2n +1 −
Eg.:
−H
Methane (CH 4 ) ⎯⎯ → Methyl radical (CH 3 −) or Me −
−H
Ethane (CH 3 − CH 3 ) ⎯⎯ → Ethyl radical (CH 3 − CH 2 − or Et −)
 CH 3 − CH 2 − CH 2 −
−H
Propane (CH 3 − CH 2 − CH 3 ) ⎯⎯ → normal
propyl or n − pr
(prifix)

and

ipr − or Isopropyl CH3 − CH −

CH3

Molecular formula C3 H 7 −
Different naming system:
We have 3 different types of naming systems which we can use for writing
nomenclature of organic compounds.
1. Trivial (or common names) or (C.N.)
2. Derived Names (D.N.)
3. IUPAC Names
1. Trivial (or common names) or (C.N.)
▪ Childhood Names of Organic Compounds
▪ In this system of nomenclature generally assigned naming to organic
compound on the basis of various properties of that compound or sources of
that organic compound.

CH 4

CH 3 − OH

O
||
H−C−O−H
O
||
CH 3 − C − OH
H−C  N H−C  N
 H 2O
H − C − OH
||
O
CH 3 − C  N CH 3 − C  N
 H 2O
O
||
CH 3 − C − O − H
Some common prefix which we can use during common names
1. Normal or n-
This prefix is used when straight C- chain is present without any C-branch
Ex.: CH 3 − CH 2 − CH 2 − CH 3 or CH 3 − CH 2
|
C.N.  n − Butane CH 2 CH 3
Ex.: CH 3 − CH 2 − CH 2 − CH 2 −
C.N.  n − Butyl radical (or group) or R −
2. Iso or iso –
This prefix we can use when one CH3 (methyl group) present as a branch (or side
chain) on second last C- of longest continuous chain.
CH 3 − CH − or Second last C −
| of chain
CH 3 CH 3 − CH −
C.N. → Isopropyl radical or ipr- Last C − CH
3 One methylgroup present
of chain asa branch
Note → Simplest iso group (or radical) is iso propyl radical
3. Neo –
When two methyl groups present as side chain on second last C- of longest
continous C-chain

CH3 One methyl group as

side chain (or branch)

CH3 − C − CH 2 −−
Last C −
CH 3 Other methyl group as
a side chain

C.N. → Neopentyl Radical

Note: Simplest Neo- will be neopentyl radical.
Type of C-atoms :
Mainly we have four type of C-atoms
(a) Primary or P or 10 C atom
That C-atom which is directly connected to one C-atom only
(b) Secondary or S or 20 C-atom
That C-atom which is directly connected to two C-atoms only.
(c) Tertiary or t or 30 C-atom
That C – atom which is directly connected to three C- atoms only.
(d) Quaternary or Q or 40 C-atom
That C-atom which is directly connected to 4 C-atoms
Problem : Write structure of following organic compounds and also write type of C-atoms.
1. n-Pentane (C.N.)
p s s s p
C−C−C−C−C or CH3 − CH 2 − CH 2 − CH 2 − CH3
2. Isopentane (C.N.) H H
p t s p
CH3 − CH − + C−C  CH3 − CH − C − C − H
CH3 p CH3 H H
3. Neopentane (C.N.) p
CH 3 CH 3
p Q p
CH 3 − C − CH 2 − + − H  CH 3 − C − CH 2 − H
CH 3 CH 3
p
Neopentyl
4. Isopropane [C.N.] (C3H8 = Molecular Formula)
CH3 − CH − + −H → CH3 − CH − H or CH 3 − CH 2 − CH 3
CH3 CH3

It is n-propane (C.N.) ? NO
Note : Here in case of C3H8  none of the other alternative structure is possible  we
can’t write here n- or iso- here we have to write only propane [C.N.]
(We can use above prefix after fourth carbon atom)
Note : We can use n- or iso- or neo- prefix only in that case when a given molecular
formula have 2 or more structural formulas.
 If we have C4H10
p s s p p t p
CH3 − CH 2 − CH 2 − CH3 & CH3 − CH − CH3
C.N. → n − Butane
CH3
C.N. → Isobutane
5. Isobutyl radical [C.N.]
p t p
CH3 − CH − + C  CH3 − CH − CH2 −
CH3 p CH3
6. Isohexane [C.N.]
p t s s p
CH3 − CH − + C − C − C  CH3 − CH − CH 2 − CH 2 − CH3
CH3 p CH3
7. Neohexane (C.N.)
p
CH3 CH3 p
p
CH3 − C − CH 2 − + C  CH3 − C − CH 2 − CH 3
s
CH3 p CH3

Note : Isooctane (C.N)

CH3 − CH − + C − C − C − C − C  CH3 − CH − CH 2 − CH 2 − CH 2 − CH 2 − CH3

CH3 CH3 Wrong Structure
Note : Iso octane is a combination of Isopropyl + Neopentyl  It has more than one branches
p
CH3 p t s CH3 p
Here 3 branches of
CH3 − CH − + − CH 2 − C − CH 3  CH3 − CH − CH 2 − C − CH3 CH3 − groups
CH3 CH3 p
CH3 CH3 p Right Structure
Note : Tertiary Alkyl group In which one valency free from C-atom
Ex.: t or Tertiary butyl group Ex.: t or Tertiary pentyl group
CH3 CH3 CH 2 − CH3
CH3 − C − or (CH 3 )3 − C − t t
CH3 − C − or CH3 − C −
CH3 CH 2 − CH3 CH3
Both are identical
t Butyl or t Bu-Group

Note : Secondary Alkyl Group In which one valency free from secondary C-atom
s s Butyl Radical
CH3 − CH − s s s
CH 3 − CH − CH 2 − CH 3 or CH 3 − CH 2 − CH − CH 3
CH 3
C.N. → Isopropyl or
s
s propyl CH 3 − CH − or
CH 2 − CH 3
We can also use some prefix during common names of some functional groups.
Functional Groups: O
||
→ − C − OH Carboxylic group → −C − H An aldehyde
||
O
O O
|| ||
→ − C − NH 2 An amide → −C − O − R An ester
Following are prefix which we can use during writing common names of above functional groups :
No. of C-atoms Prefix
1C → Form
2C → Acet
3C → Propion n-
4C → Butyr Iso-
n-
5C → Valer Iso-
3 C + (=) bond → Acryl Neo-
4 C + (=) bond → Croton
Problem : Write structures from following common names
Ex.: 1 Formaldehyde [C.N.]
 Ex.: 4 n-Butyraldehyde [C.N.]
Form + Aldehyde O O
O O
|| || C−C−C−C−H ; CH3 − CH 2 − CH 2 − C − H
H − + − C − H or H − C − H
Ex.: 2 Acetaldehyde (C.N.) Ex.: 5 Isobutyraldehyde [C.N.]
 O O
O
CH3 − CH − + − C − H  CH 3 − CH − C − H
C+ −C−H → CH 3 − C − H
CH3 CH3
O
Ex.: 3 Propionaldehyde [C.N.] Ex.: 6 n-Valeraldehyde [C.N.]
O CH3 − CH 2 − CH 2 − CH 2 − C − H
CH3 − CH 2 − C − H O
Ex.: 7 Neo Valeraldehyde [C.N.]
CH3 O CH 3 O
CH 3 − C − CH 2 − +−C−H  CH 3 − C −− C − H

CH3 CH 3

Ex.: 8 Acryldehyde [C.N. also Acrolein]

O O
C = C−C−H or CH 2 = CH − C − H
(the double bond will always come after adjacent carbon atom of functional group in
“Acryl” or in “Croton”)
Ex.: 9 Crotonaldehyde [C.N.]
O O
C−C = C−C−H or CH3 − CH = CH − C − H
Ex.: 10 Formic Acid [C.N.] Ex.: 11 Acetic Acid [C.N.]

 
Form + Carboxylic acid Acet + acid
O O O O
H −− + − C − OH or H − C − OH C + −− C − OH or CH 3 − C − OH

Ex.: 12 Propionic acid [C.N.] Ex.: 16 Isovaleric acid

Ex.: 13 n-Butyric acid [C.N.] Ex.: 17 Neovaleric acid

Ex.: 14 Isobutyric acid [C.N.] Ex.: 18 Crotonic acid

Ex.: 15 n-Valeric acid [C.N.] Ex.: 19 Acrylic acid

 2. DERIVED NAMES [D.N.]
In this naming system, we generally derive higher  Simplest member of
alcohol family
homologous of given family with the help of
simplest member of that family. C OH Carbinol [C.N.]

 Homologous  Two consecutive members of given + CH

Ex. CH 4 ⎯⎯⎯ 2 + CH
→ C2 H 6 ⎯⎯⎯ → C3 H 8
2
family (should be same family) in which difference
of –CH2− (Methylene) group is present
Homologous (family should be same)
members of Alkane family
 Simplest member of alkane family = Methane C
Problem : Write structures from
 Simplest member of alkene family following derived names
1. Ethyl, methyl methane [D.N.]
C=C Ethylene [C.N.] H
CH3 − CH 2 − + CH3 − + − C −  CH3 − CH 2 − C − Hor
 Simplest member of alkyne family CH3
−C  C − Acetylene [C.N.]
C.N.  n − Butane  CH 3 − CH 2 − CH 2 − CH 3
 2. Ethyl, di-methyl, propyl methane [D.N.]
 Unsaturated Organic
Compounds
CH3 − CH 2 − + 2CH3 − + CH3 − CH 2 − CH 2 − + − C −
Where C = C or C  C
Di, tri, tetra = Prefix = we don’t consider first bonds also present
alphabet of these prefix while writing derived or Case-I Alkene → Alk + ene
IUPAC names. word root P suffix
CH3

Type of bonds between
CH3 − CH 2 − CH 2 − C − CH3 two C − atoms
CH 2 − CH3  Simplest member of alkene
family contains = 2 C− atoms
3. Isopropyl methane [D.N.]
H H
C=C or CH 2 = CH 2 or C 2 H 4
CH 3 − CH − + −C− H H
CH 3 C.N. = Ethylene, IUPAC = Alkene (Ethene)
or CH 3 − CH − CH 3 Isobutane [C.N.] General formula of alkene family = CnH2n
where n = no. of C-atoms = 2, 3, 4, …. etc.
CH3
 n = 3 C3 H 6  n = 4 C4 H8   − Butylene (C.N.)
CH 3 − CH = CH 2  − Butylene (C.N.) 4 3 2 1
C.N. → Propylene 4 3 2 1 CH3 − CH = CH − CH3
I.U. → Propene
CH3 − CH 2 − CH = CH 2

Note →  ,  ,  → Prefix
→ Used to denote position of C = C
→  − butylene is not possible
( ) ( ) ( )
→  − Hexylene CH 3 − CH 2 − CH = CH − CH 2 − CH 3

Case − III Alkyne → Alk + yne

(IUPAC name) word root P suffix

Type of bonds between
two C-atoms (C = C)
 Simplest member of alkyne family contains = 2C − atoms
H H or CH  CH or
CC C2 H2
C.N. = Acetylene (used in welding purpose or in artificial ripening of fruits)
IUPAC = Alkyne(Ethyne)
Generalformula of alkyne family = C n H 2n − 2 where n = no. of C − atoms = 2,3, 4..... etc.

Pr oblem : Write structure from following derived names

(i) Ethyl Ethylene [D.N.]

CH3 − CH 2 − + C=C  CH3 − CH 2 H

C=C
(ii) Tetra methylethylene[D.N.] H H
CH 3 CH3
4 CH3 − + C=C  C=C
CH 3 CH 3
(iii) Dimethyl ethylene[D.N.]

H CH3 CH3 CH3

C=C C=C
H CH 3 H H
Unsymmetricalor unsym − Symmetricalor sym −
Dimethylethylene Dimethyl ethylene

Note → Symmetrical (Sym −) → Equaldistribution of two alkylgroups on two doubly

bonded C − atoms
Unsymmetrical (Unsym −) → Unequal distribution of twoalkylgroups
(iv) Unsym. Ethyl, methylethylene[D.N.] (vi) Sym. Diethyl ethylene [D.N.]

CH3 − CH 2 H CH3 − CH 2 CH 2 − CH3

C=C C=C
CH3 H H H

(v) Sym. Ethyl, methylethylene[D.N.] (vii) Ethyl, methylacetylene [D.N.]

CH3 CH 3 − CH 2 − +CH 3 − + − C  C −
CH3 − CH 2
C=C CH 3 − CH 2 − C  C − CH 3
H H
(viii) Ethyl,isoproprylacetylene[D.N.]
CH3 − CH 2 − + CH3 − CH − + − C  C − ; CH3 − CH 2 − C  C − CH − CH 3

CH3 CH3

(ix) Ethyl, methyl carbinol [D.N.]

CH3 CH3
CH3 − CH 2 − + CH3 − + − C − OH  CH3 − CH 2 − C − OH or CH3 − CH 2 − CH − OH
H
Pr oblem : Write structure from following derived names
(x) Neo pentyl,isopropylacetylene [D.N.]
(xi) Diisopropyl methane [D.N.]
(xii) Isopropyl, neopentylcarbinol[D.N.]
(xiii) t Butylcarbinol[D.N.]
 SOLUTION :
CH3 H
(x) CH 3 − C − CH 2 − + CH 3 − CH − + − C  C − (xi) CH 3 − CH − C − CH − CH 3
CH3 CH3 CH3 H CH3
CH3
CH3 − C − CH 2 − C  C − CH − CH 3
CH3 CH3

CH 3 H CH 3
(xii) CH − C − CH − C − OH (xiii) CH 3 − C −−CH 2 − OH
3 2

CH 3 CH − CH 3 CH 3
CH3
Case-III IUPAC names :
 International Union of pure and applied chemistry
 Most authentic naming system.
 For writing IUPAC names of organic compounds we have to follow certain rules.
Rule I : We have to select longest continuous C-chain in given organic compound

C C C C C C C C C C

C C C C C
or
Side chain / branch C
C

C C C C

C
Rule II : We have to assign numbering to longest continuous C-chain. We can assign
numbering from any of the two ends of longest C-chain. For this we have to
follow IUPAC rule i.e. select “Lowest Set of Locant rule”.

LOCANT

All substituents Double or All functional

Like –F (Fluoro) | −Cl (Chloro) Triple bonds groups
−Br (Bromo) | −I (Iodo) p suffix s suffix
−NO2 (Nitro | −C6H5 (Phenyl) etc.
or C−side chains  CH3− (methyl)
or C2H5− (Ethyl) or (CH3)2−CH−
(isopropyl) etc.
Prefix
Rule III (Step 3)
Ex.:
CH3 CH 2 CH CH 2 CH CH 2 CH3

CH 2 − CH3 CH − CH 3 Wrong selection with 7C-atoms

CH3 in parent chain & 2C − sidechains
or

CH3 CH 2 CH CH 2 CH CH 2 CH3

CH 2 − CH3 CH − CH3
Right selection
CH3 here 7C-atoms in parent
C-chain with three C-side chains

Statement: If in a given organic compound 2 or more longest C-chains (parent C-

chain) with same number of C-atoms are possible then that will be final
parent C-chain on which number of C-side chains are maximum.
 CH3 CH2 CH CH2 CH3 Right selection
(5C − atomsin parent chain
CH3 C CH3 with 3 C − sidechains)

CH3

Rule – IV Ex: CH3 CH 2 C C CH 2 CH3 Wrong selection

(with 6C − atoms in
CH 2 CH 2 parent chain )

Alternatively, CH3 CH 2 C C CH 2 CH3 Right Selection

(with 4C − atomsincluding
CH 2 CH 2 2doubly bonded C − atoms)

Statement: In a given organic compound we have to select C-atom of functional group or

C-atom of double / triple bonds, irrespective of the length of longest
continuous (i.e. parent C-chain) C-chain.
• Priority order of functional group / double or triple bond / substituents in IUPAC
Allsubstituents Alkyne Alkene Allfunctional groups
names. ⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯→ Increasing order of priority

* Correct order of writing IUPAC names

Pr efix + Alk + p suffix + s suffix Represent all
  functional group
No.of Type of
C − atoms bond between
(word C − atoms
root)
Prefix → Allsubstituents like − F / − Cl / − Br / − I / − NO 2 / − C 6H 5 etc.or allC − sidechains
(−Me / − Et etc.)
p suffix → s suffix →
C − C  ane ; C = C  ene ; C  C  yne All functional groups
 Problem: Write IUPAC name & structures of following compounds.
(1) n-Pentane [C.N.]
CH3 − CH2 − CH2 − CH2 − CH3 I.U.  Pentane

(2) Isopentane [C.N.]

CH3 − CH − CH 2 − CH3 I.U. → 2 − Methyl butane
1 2 3 4 Prefix Alk p suffix
CH3
(3) Neopentane [C.N.]
CH3 1 2
CH3 3

CH3 − C − CH 2 − H or CH3 − C − CH3 L to R = 2, 2 or R to L = 2, 2

CH3 CH3

I.U. → 2, 2 − Dimethylpropane
Prefix Alk p suffix
(4) Isooctane (Isopropyl + Neopentyl) (6) t Butyl,Isopropylmethane [D.N.]
CH3 CH 3 H
5 4 3 2 1 1 2 3 4 5
CH3 − CH − CH 2 − C − CH3 CH 3 C C CH CH 3

CH3 CH3 CH 3 H CH 3
I.U. → 2, 2, 4 − Trimethylpentane
L to R → 2, 2, 4 R to L → 2, 4, 4
R to L → 2,2,4 ; L to R → 2,4,4
IUPAC → 2, 2, 4 − Trimethyl pentane
(5) Ethyl methyl methane[D.N.] Prefix Alk p suffix
(7) Tetra methylethylene [D.N.]
CH3 − CH2 − + CH3 − + − C − 4
3
CH3 CH3
H 4 − CH3 + C=C  C=C
CH 3 − CH 2 − C − CH 3 I.U. → Butane CH3 2 CH3
1
H
IUPAC → 2,3 − Dimethyl but − 2 − ene
or CH3 − CH 2 − CH 2 − CH3 Prefix Alk p suffix
(8) Sym. Ethyl,methylethylene [D.N.]

CH3 CH 2 − CH3 1 2 3 4 5 L to R = 2
C=C or CH3 − CH = CH − CH 2 − CH3
R to L = 3
H H

I.U. → Pent − 2 − ene

Alk p suffix

(9) Unsym. Ethyl,methyl ethylene [D.N.]

CH3 CH3 CH3

H
or CH 2 = C or CH 2 = C
C=C
CH 2 − CH3 CH 2 − CH3
H CH 2 − CH3 1
2
3 4

IUPAC → 2 − Methyl but − 1 − ene

Prefix Alk p suffix
Pr oblem : Write structures & IUPAC names (2) Sym. dimethylethylene[D.N.]
of following organic compounds.
CH 3 CH 3
(1) Tetra ethyl methane[D.N.] C=C
(2) Sym.dimethylethylene[D.N.] I.U. → But − 2 − ene
H H
(3) Unsym.Dimethyl ethylene [D.N.]
1 2 3 4
(4) Ethyl,isopropylacetylene[D.N.]
CH 3 − CH = CH − CH 3
(6) Acetylene[C.N.]
(7) Diisopropylacetylene[D.N.]
(3) Unym. dimethylethylene[D.N.]
Solution. :
CH3 H CH3
(1) Tetra ethyl methane[D.N.] C=C → C = CH 2
CH 2 − CH3 CH3 H CH3 2 1

3
CH3 − CH 2 − C − CH 2 − CH 3 I.U. → 2 Methylprop − 1 − ene
1 2 3 4 5
CH 2 − CH3
I.U. → 3,3 − Diethyl pentane
(4) Ethyl, isopropyl acetylene [D.N.] 6 5 4 3 2 1

CH3 − CH 2 − + CH3 − CH − + − C  C − CH3 − CH 2 − C  C − CH − CH3

CH3
CH3
I.U. → 2 − Methyl hex − 3 − yne
(5) Diethylacetylene [D.N.]
6 5 4 3 2 1

CH3 − CH 2 − C  C − CH 2 − CH3 I.U. → Hex − 3 − yne

(6) Acetylene [C.N.]

CH  CH
Ethyne
(7) Diisopropylacetylene [D.N.]
6 5 4 3 2 1

CH3 − CH − C  C − CH − CH3 I.U. → 2,5 − Dimethyl hex − 3 − yne

CH3 CH3
 Some Complex alkyl radicals, their common and IUPAC names:
Ex.: C.N. → Isopropyl radical Ex.: C.N.  t − Butyl radical
2 1
CH 3
CH 3 − CH − 2
1 2 3 4 5 6 7 8
CH3 − CH 2 − CH 2 − CH − CH 2 − CH 2 − CH 2 − CH3
CH 3 − C −
CH 3 1 CH − CH3
Complex C − side
I.U. → 1 − Methylethyl CH 3 2 CH 3 chain

Ex.: C.N. → Neopentyl radical

I.U. → 1,1 − Dimethylethyl I.U. → 4 − Isopropyloctane (correct)
CH3
Alternatively → 4 − (1 − Methylethyl)
CH 3 − C − CH 2 −− Ex.: C.N. → Sec. Butyl radical octane (More correct)
CH3 1
I.U. → 2, 2 − Dimethylpropyl Ex.: C.N. → Isobutyl radical
CH3 − CH −
Ex.: C.N. → t − pentyl radical 3 2 1
2 CH 2 − CH 3 3
2 CH2 − CH3 3 CH3 − CH − CH 2
CH 3 − C −−− I.U. → 1 − Methylpropyl
CH 3
1
CH 3 I.U. → 2 − Methylpropyl
I.U. → 1,1 − Dimethylpropyl
 LECTURE – 2
IUPAC of Functional groups and
priority order of functional
groups
 Functional Groups ( s suffix) :
given family with several members in which difference of – CH2 − (methylene)
 Agroup is noticeable between 2 consecutive members.
 For a particular family containing functional group have same chemical properties
(like chemical reaction) but different physical properties (like melting or boiling
points, solubilities etc.)
(1) Alcohol (R – OH; Alkyl alcohol)
+ ol
Gen. IUPAC → Alk + ane
word p s suffix
root
suffix represent alcohol

Prefix  Hydroxy
Rule of IUPAC
If first alphabet of s suffix begins from any vowel (a, e, i, o, u) then we have to omit
last alphabet of p suffix)
Simplest alcohol contains = 1 C Ex.: Isopropyl alcohol [C.N.]
1CH3 − OH (0 alcohol) 3 2
Trivial or common name → carbinol or wood spirit CH 3 − CH − OH
IUPAC → Methan – 1 – ol or Methanol
CH3 1
Next homologous
2 1 I.U. → Propan − 2 − ol
CH3 − CH 2 − OH Ex.: Neopentyl alcohol [C.N.]
D.N. → MethylCarbinol
CH 3
C.N. → Ethyl alcohol
I.U. → Ethan − 1 − ol or Ethanol CH 3 − C − CH 2 − OH
3 2 1
Ex.: C.N. = Propylalcohol CH 3
CH3 − CH 2 − CH 2 − OH I.U. → 2, 2 − Dimethylpropan − 1 − ol
3 2 1

I.U. → Propan − 1 − ol or Propanol

(2) Thiol (R − SH; Alkyl thiol)
Gen. IUPAC → Alkanethiol  Alk + ane + thiol
word p s suffix
root
suffix represent thiol
Prefix → Mercapto

 Simplest thiol contains = 1C  Next homologous

1
CH 3 − SH 2 1
CH 3 − CH 2 − SH
C.N. → Methyl thiol C.N. → Ethyl thiol
I.U. → Methane thiol I.U. → Ethane − 1 − thiol or Ethane thiol
Ex.: Isobutyl Thiol [C.N.]
CH3 − CH − CH 2 − SH
2 1
CH3
3
I.U. → 2 − Methyl propane − 1 − thiol
s suffix
(3) Ether (R − O − R)
(Prefix)
Gen. I.U. → alkoxyalkane  Alk + oxy + alk + ane
( p suffix)
Pr efix → Alkoxy  
In which Chain
Simplest ether contains less no. where more
of C − atoms C − atoms
= 2C
CH 3 − O − CH 3 → Alkoxy

C.N. = Dimethyl ether; IUPAC → 1 − Methoxymethane

1 2 1 2
Ex.: CH 3 − O − CH 2 − CH 3 or CH 3 − O − C 2H 5 Ex.: CH 3 − CH 2 − O − CH 2 − CH 3
C.N. → Ethyl, methyl ether (Wrong = Methyl,ethylether)
C.N. → Diethylether
I.U. → 1 − Methoxyethane
I.U. → 1 − Ethoxy ethane
 2 1
Ex.: CH 3 − CH 2 − O − CH − CH 3 or C 2 H 5 − O − CH(CH 3 ) 2

3 CH3

C.N. → Ethyl, isopropylether

I.U. → 2 − Ethoxypropane
2 1 2 1
Ex.: CH3 − CH − O − CH − CH3
CH3 3 CH3

C.N. → Diisopropyl ether

I.U. → 2 − Isopropoxy propane
or
→ 2 − (1 − Methyl ethyl) oxypropane
 (4) Thioether (R − S − R)
Gen. IUPAC → Alkylthio alkane Simplest thio ether contains = 2C

prefix CH 3 − S − CH 3
 p suffix

Less no Parent C.N. → Dimethylthio ether
of C − atoms C − chain with I.U. → Methylthio methane
more no of
C − atoms
1 2 1 2
Ex.: CH 3 − S − CH 2 − CH 3 or CH 3 − S − C 2H 5 Ex.: CH 3 − CH 2 − S − CH 2 − CH 3
C.N. → Ethyl Methylthio ether C.N. → Diethylthio ether
I.U. →1 − Methylthio ethane I.U. →1 − Ethylthio ethane
2 1
Ex.: CH 3 − CH 2 − S − CH − CH 3
3 CH3
C.N. → Ethyl,isopropylthio ether
I.U. → 2 − Ethylthio propane
5. Carbonyl compounds Gen. IUPAC  Alkanal
In which carbonyl group is present

O or  + al
Alk + ane
word p s suffix i.e.
C root
suffix IUPAC
O
− C−  Pr efix for aldehydes → Formyl & oxo
Ex.: Simplest aldehyde contains → 1C
O
C.N. → Formaldehyde
Aldehydes Ketones H−C−H I.U. → Methan − 1 − al or Methanal

Case − I Aldehydes
Ex.: Acetaldehyde [C.N.]
O
O
− C−H or − CHO 2
CH3 − C − H or CH3 − CHO
Note : In aldehydes, one valency of carbonyl 1
group always filled by H-atom & other valency
can be filled by R- (Alkyl group) or H-atom. I.U. → Ethan − 1 − al or Ethanal
Ex. : Propionaldehyde [C.N.] Ex. : Isovaleraldehyde [C.N.]
O 4 3 2
O
CH3 − CH − CH 2 − C − H
CH3 − CH 2 − C − H 1
3 2 1 CH3
I.U. → Pr opan − 1 − al I.U. → 3 − Methylbutan −1 − al

Ex.: Isobutyraldehyde [C.N.] Ex.: Acryldehyde (or Acrolein) [C.N.]

O O
O 3 2
3 2
C = C−C−H or CH 2 = CH − C − H
CH 3 − CH − C − H 1
1
CH3 I.U. → Prop − 2 − en − 1 − al or Prop − 2 − enal
s suffix Ex. : Crotonaldehyde [C.N.]
I.U. → 2 − Methyl propan − 1 − al CH3 − CH = CH − C − H
4 3 2 1
Prefix Alk p O
suffix
I.U. → But − 2 − en − 1 − al or But − 2 − enal
 Ex.: Neovaleraldehyde [C.N.]
Simplest member of ketone family → 3C
CH3 CH3 O
O
3 1
CH3 − C − CH 2 − → CH 3 − C −−C −−H 2
3 2 1 CH3 − C − CH3 (C3H 6O)
CH3 CH3
C.N. → Dimethyl ketone
I.U. → 2, 2 − Dimethyl propan − 1 − al (or ACETONE = Acetyl + Ketone)
Prefix Alk p s suffix I.U. → Pr opan − 2 − one (Wrong IUPAC)
suffix
 Pr opanone it is simplest ketone
Case − II Ketones
O therefore here no need to mention
position of carbonyl group
R −C− R or R − CO − R
Gen. IUPAC → Alkanone or Alk + ane + one O
word
root
p s suffix Note → CH3 − C −
suffix i.e.IUPAC
Acetyl or Ac −−
Prefix → Keto or oxo
 O O O CH3
1 3 4 4 1
Ex.: CH3 − C − CH 2 − CH3 or CH3 − C − CH 2 − CH3 1
2 3 2
Ex.: CH 3 − C −−C − CH 3
wrong solution 2 3 4
C.N. → Ethyl, methyl ketone CH 3
C.N. → t − Butyl, methyl ketone
I.U. → Butan − 2 − one
IUPAC → 3,3 − Dimethylbutan − 2 − one
Alk p suffix s suffix

(6) Cyanide ( −C  N) or − CN
5 4
O 2 1
3 Gen. IUPAC  Alkanenitrile or
Ex.: CH 3 − CH 2 − C − CH − CH 3 Alk + ane + nitrile
R to L → 2,3 CH3 word p s suffix
L to R → 3, 4 root
suffix
C.N. → Ethyl, isopropyl ketone Prefix → Cyano
Simplest member of cyanide = 1C
I.U. → 2 − Methyl pentan − 3 − one C.N. → Formonitrile (or Hydrogen Cyanide)
Prefix Alk p suffix s suffix I.U. → Methane − 1 − nitrile or Methanenitrile
 2 1
Ex.: CH3 − C  N; IUPAC → Ethane nitrile  Simplest isocyanide contains = 2C
=
CN → Acetonitrile [or Methylcyanide] CH 3 − N = C H − N C
Unstable
Ex.: CH 3 − CH − C  N
3 2 1 C.N. → Methylisocyanide
CH3 I.U. → Methane − 1 − carbylamine
C.N. → Isopropylcyanide
I.U. → 2 − Methylpropanenitrile 2 1
Ex.: CH 3 − CH 2 − N = C
(7) Isocyanide ( − N = C) or ( − NC)
Donor acceptor C.N. → Ethyl isocyanide
Gen. IUPAC → Alkane carbylamine I.U. → Ethane − 1 − carbylamine
or alk + ane + carbylamine Ex.: CH3 − CH − N = C
 p Suffix i.e.
Parent suffix represent CH3
C − chain iso cyanide C.N. → Isopropylisocyanide
functional group
Prefix → Carbylamino I.U. → Propane − 2 − carbylamine
 Carboxylic acids and their derivatives
O
−C −O − H
Carboxylic group

O O O O O
−C − X − C − NH 2 −C −O − R −C−O −C− R
Acid halide Amide Ester Anhydride

( − X = − Cl / − Br)
O
 Carboxylic group (− C − O − H or − COOH)
Gen IUPAC name  Alkanoic acid
or
Alk + ane + oic acid
word p suffix s suffix i.e.
root IUPAC
Prefix for carboxylic group - Carboxy
 Simplest carboxylic acid contains → 1 C  Isobutyric acid (C.N.)
O O
3 2
H − C − OH or H − COOH CH 3 − CH − C − O − H
1
C.N. → Formic acid CH3
I.U. → Methanoic acid
I.U. → 2 − Methylpropan − 1− oic acid
 C.N. → Acetic acid
Pr efix Alk p s suffix
O suffix
2
CH 3 − C − O − H  Neovaleric acid (C.N.)
1 CH3 O
I.U. → Ethanoic acid
CH 3 − C −−− C − O − H
2
 Propionic acid = C.N.
3 CH3
1
O
3 2
CH3 − CH 2 − C − OH I.U. → 2, 2 − Dimethylpropan − 1 − oic acid
1

I.U. → Propanoic acid

 Acrylic acid (C.N.)
 n-Butyric acid (C.N.)
O
CH3 − CH 2 − CH 2 − C − O − H
CH 2 = CH − C − OH
O
or
I.U. → Butanoic acid or Butan − 1 − oic acid
O
3 2
CH 2 = CH − C − O − H
1

I.U. → Prop-2-en-1-oic acid

Alk p suffix s suffix

 Crotonic Acid (C.N.)

O
CH3 − CH = CH − C − O − H
4 3 2 1
I.U. → But − 2 − en − 1 − oic acid
IUPAC naming of derivatives of carboxylic acids
O O
(i) Acid halide or Acid chloride − C − X or −C − Cl

Gen IUPAC name → Alkanoyl chloride

Alk + an + oyl chloride
word p s suffix
root suffix

Prefix → Halocarbonyl
* Simplest acid halide contains = 2 C Because unstable organic compound formed
O O
CH3 − C − Cl CH3 − C − Acyl (or Acetyl)
I.U. → Ethanoyl chloride Ac −
O
Ex.: CH3 − CH 2 − C − Br I.U. → Propanoyl bromide
 O O O O
H R H
or −C − N Ex.: H − C − N or H − C − NH 2 p Amide
(ii) Amide −C − N
H H H
p amide s amide
C.N. → Form + amide = Formamide
O I.U. → Methanamide
R
or −C − N
O
R p Amide
t amide
Ex.: CH 3 − C − NH 2 or Ac − NH2
C.N. → Acetyl + amide (Acetamide)
Gen IUPAC name → Alkanamide I.U. → Ethanamide or Ethan − 1 − amide
or
O
Alk + an + amide
word p suffix s suffix Ex.: CH3 − CH2 − C − NH2 p Amide
root
C.N. → Propionamide
Prefix → Carbamoyl or Amido I.U. → Propanamide
 O H
2
Ex.: CH 3 − C − N s amide Ex.:
1 CH 3 O CH3 t amide
I.U. → N − Methylethanamide CH 3 − C − N
s amide CH 2 − CH3
O H
Ex.: CH 3 − CH 2 − C − N I.U. → N − Ethyl, N − Methylethanamide
3 2 1
CH 2 − CH3
I.U. → N − Ethylpropanamide Ex.:
O CH 2 − CH 3
2
O t amide
CH 3 t amide CH 3 − C − N
Ex.: CH 3 − C − N 1
CH 2 − CH 3
CH 3
I.U. → N, N − Diethylethanamide
I.U. → N, N − Dimethylethanamide
 O
(iii) ESTER (−C − O − R or − COOR)
Note → alkanoate
Gen IUPAC name → Alkylalkanoate s suffix
Rest C − chain including carbonyl group
p suffix
Pr efix
used for R − group
directlyconnected to 'O'

Pr efix → Carbalkoxy and Alkoxycarbonyl

O O

Ex.: 1 H − C − O − CH3 Ex.: 2 CH 3 − C − O − CH 3

Alkyl C.N. → Methylacetate
C.N. → Methyl formate
I.U. → Methylethanoate
I.U. → Methylmethanoate or
Methyl ethan − 1 − oate
 O O
Ex.: 3 CH3 − CH 2 − C − O − CH 3 Ex.: 4 CH 2 = CH − C − O − CH 2
3 2 1
C.N. → Methylpropionate CH3
C.N. → Ethylacrylate
I.U. → Methylpropanoate
I.U. → Ethylprop − 2 − en − 1 − oate
O O
4 3 2 3 2
Ex.: 5 CH3 − CH = CH − C − O − CH3 Ex.: 6 CH 3 − CH − C − O − CH 3
C.N. → Methylcrotonoate 1

I.U. → Methylbut − 2 − en − 1 − oate C.N. → Methylisobutyrate

I.U. → Methyl − 2 − Methylpropanoate
(iv) Anhydride → Derived from carboxylic acids
O O

−C − O
 − H −C 
+ 
⎯⎯⎯⎯→ H2O +
Dehydration
O 
 −C
−C − O
 − H
O
O
Two molecules of Anhydride
carboxylic acid
I.U. → Alk an oicanhydride Prefix → No prefix for
I.U. → Alkanoicacid
s suffix anhydride
Case I → If number of C-atoms on both sides of ‘O’ atoms are same in given
anhydride then
sum of C-atoms Number of C-atoms
=
2 i.e. parent chain
O
CH 3 − C C.N. = Acetic anhydride (Acet for 2C – atoms)
Ex.: O
CH 3 − C I.U. = Ethanoic anhydride

O
O
CH 3 − CH 2 − C
Ex.: O C.N. Propionic anhydride (Propion for 3 C-atoms)
CH 3 − CH 2 − C I.U. = Propanoic anhydride
O
 O
CH 3 − CH 2 − CH 2 − C
C.N. = n-Butyric anhydride
Ex.: O
I.U. = Butanoic anhydride
CH 3 − CH 2 − CH 2 − C
O
Case II - If no. of C-atoms on both sides of O atom are different then we have to assign
IUPAC for individual chain.
O O
CH3 − C CH 3 − CH 2 − C
Ex.: Ex.:
O O
CH3 − CH 2 − C CH 3 − CH 2 − CH 2 − C

O O
C.N. = Acetic, propionic anhydride C.N. = n-Butyric, propionic anhydride
I.U. = Ethanoic, propanoic anhydride I.U. = But anoic propanoic anhydride
 2 1
Amines (they are derived from NH 3 ) C.N. = Ethylamine
Ex.: CH 3 − CH 2 − NH 2
I.U. = Ethan-1-amine
NH 3
3 2
p amine s amine
Ex.: CH 3 − CH − NH 2 I.U. → Propan − 2 − amine
t amine
R
R − NH2 R −N H−R R−N 1 CH3
(− N H 2 ) (− N H −) (− N ) R
Case − II s − amine (R − NH − R)
Case I → p amine(R − N H2 ) Gen. IUPAC name → N − Alkyl alkanamine
Gen. IUPAC name → Alkanamine 
Prefix; contains Parent C-chain i.e.
s suffix less no of C atoms more no. of C atom
Prefix → amino

Ex. simplest p amine → 1c Prefix → N − Alkylamino

Simplest s aminecontains = 2c
CH 3 − N H 2 C.N. → Methylamine
I.U. → Methan − 1 − amine CH3 − NH − CH3 C.N. → Dimethyl amine
I.U. → N − Methylmethaneamine
 Simplest t aminecontains = 3C
Ex.: CH 3 − NH − CH 2 − CH 3
C.N. → Ethyl, methylamine CH3
CH 3 − N C.N. → Trimethylamine
I.U. → N-Methylethan-1-amine 1 I.U. → N, N − Dimethyl
CH3 methan amine
2 1
Ex.: CH 3 − CH 2 − NH − CH − CH 3 CH 2 − CH 3
Ex.: CH 3 − N
3 CH3
CH 2 − CH3
I.U. → N − Ethyl propan − 2 − amine 1 2

C.N. → Diethyl,methylamine
R
Case − III t − amine R−N I.U. → N-Ethyl, N-Methyl ethanamine
R
CH 2 − CH3
Gen. IUPAC name → N, N − Dialkylalkanamine Ex.: CH 3 − CH 2 − N
CH 2 − CH 2 − CH 3
Pr efix; represent 1 2 3
less no of C − atoms
C.N. → Diethyl, propylamine
Prefix → N,N − Dialkyl amino
I.U. → N, N − Diethylpropanamine
Note : In amides NH2 group directly connected with carbonyl group.
O
− C − NH 2
Amide
Whereas in case of Amines, NH2 group is always connected to Alkyl group, no role of
carbonyl group R − N H 2
Amine
 LECTURE – 3
IUPAC of Multifunctional groups
(Prefix and suffix)
 Priority order of various functional groups
Functional Group Name Functional Group Name
O O O
Carboxylic acid
(i) − C − OH (iii) −C − O − C − Anhydride
S Suffix = (Alk + 1)anoic acid or
S Suffix = (Alk + 1) anoic anhydride or Alkanoic
Alkanoic acid
anhydride
Prefix = Carboxy No prefix
O O
(ii) − S − OH Sulphonic acid (iv) −C − O − R Ester
S Suffix = Alkyl (Alk+1)2 anoate or
O Alkylalkanoate
S Suffix = Alkane sulphonic acid Prefix = Alkoxy carbonyl & carbalkoxy
O
Prefix = Sulpho
(v) −C − Cl Acid Chloride
S Suffix = Alkanoyl chloride
Prefix = Chlorocarbonyl
Functional Group Name Functional Group Name
(vi) − C − NH 2 Amide (x) − C − R Ketone
O O
S Suffix = (Alk + 1) amide S Suffix = Alkanone
Prefix = Amido or Carbanoyl Prefix = Keto / oxo
(vii) −C  N Cyanide (Cya) (xi) −OH Alcohol
S Suffix = Alkanol
S Suffix = Alkanenitrile Prefix = Hydroxy
Prefix = Cyano
(viii) − N = C Isocyanide (xii) − SH Thiol
S Suffix = Alkane thiol (Mercapto)
S Suffix = Alkanecarbylamine or AlkaneIsonitrile
Prefix = Carbyl amino or Isocyano
Prefix = mercapto
O (xiii) − NH 2 Amine
(ix) − C − H Aldehyde S Suffix = Alkanamine
S Suffix = Alkanal Prefix = Amino
Prefix = Formyl / oxo
Functional Group Name
(xiv) −CH = CH − Alkene (Alk)
No secondary suffix & prefix (only primary suffix)
(xv) −C  C − Alkyne (Alk)
No secondary suffix & prefix (only primary suffix)
(xvi) All substituents (like – F, – Cl, – Br, – I) or Ether all are treated as substituents
Bond line notations 4 C C 3
CH 2 or
CH 3
or 1 C C 2
CH3 CH 2 Butane
I.U. → 1 − Methylcyclobutane
C CH3
2 1
CH CH 2 or C C C
But −1 − yne
Problem: Write IUPAC names : or
C C C
3 4
I.U. → 2, 2 − Dimethylpropane I.U. → 2,3 − Dimethylbutane
3
C C

A 1 2 or
or C C
C C
C C
I.U. → 1,2 − Dimethylcyclopropane I.U. → Propane
 2 1 Ex :
1
3
C C
or C C
3 C 2
4 or C
4
I.U. → 2 − Methylbutane C C
6
C C
7 C C 5 C

or Butane (I.U.) I.U. → 4,4 − Dipropylheptane

5 3
6 1
4 2
Ex :
7 9 11
8 10

I.U. → 6,7 − Diethyl − 3 − methyl

undec − 2 − ene
 Organic Bond line Organic Bond line
compounds notations compounds notations
O O O
O O O
C H H 5. C C
1.
CH3 O O CH3 O CH3 O
O O
C 6. CH 3 − CH − C
2. or
H C
CH 3 H
CH 3 C
O O (Isopropyl)
3. C
CH 3
CH 3 CH 3 C
7. CH3 − C − C C or
H C
CH2 H CH 3
4.
CH3 O O ( t Butyl radical)
Naming of Polyfunctional organic compounds :
O I
O I
C CH OH OH
Ex. CH3 C
or
CH
Br O Br O

O I
4 2
5 C 3 CH 1 OH SFG (Senior functional group)
Solution: CH3 CH C (Suffix will be used)

JFG Br O
(Junior functional
group; Prefix)
I.U. → 3 − Bromo − 2 − iodo − 4 − keto pentan − 1 − oicacid
prefix
2 3
CH = CH
Ex. Amine I.U. → 3-Amino prop - 2-en -1-al
C 1 NH 2
O Pr efix Alk p Suffix
H
 Br CONH 2 O Br CONH 2
COOH
CH CH C − OH or
Ex. CH 3 CH CH
CHO COCl
CHO COCl

Br JFG CONH 2 O
5 3
6 CH 4 CH 2 C − OH
Solution: CH CH CH 1
3

CHO COCl
JFG JFG

I.U. → 3 − Amido − 5 − bromo − 2 − chlorocarbonyl − 4 − formyl hexanoic acid

or
I.U. → 5 − Bromo − 3 − carbamoyl − 2 − chlorocarbonyl − 4 − formyl hexanoic acid
 Note : Ester as a junior functional group
l When carbalkoxy (Prefix) used for an ester ?
O O Connectivity of an ester
through 'O' with longest
CH3 − C − O − CH 2 − CH 2 − C − O − H 'C' chain
I.U. → 3 − Carbethoxy propanoic acid

l When alkoxycarbonyl (Prefix) used for an ester ?

O O
3 2
CH3 − O − C − CH2 − CH2 − C − OH
1
I.U. → 3 − Methoxycarbonyl propanoic acid
Connectivity of an ester
through carbonyl with
longest 'C' chain

O
6 5 4 2 1
Ex.: CH − CH − CH − C − CH − CH I.U. → 2 − Bromo − 5 − hydroxy hexan − 3 − one
3 2 3
3
Prefix
OH Br
 Note : Aldehyde as a junior functional group
l When Formyl (Prefix) used for an Aldehyde ?
O
4 3 2
Ex.: CH 3 − CH 2 − CH − C − OH
1
C
O H Pr efix → formyl
I.U. → 2 − Formyl butan − 1 − oicacid

l When Oxo (Prefix) used for an Aldehyde ?

O
2 1
Ex.: CH 3 − CH − C − OH
3 C−H Pr efix → oxo
O
I.U. → 2 − Methyl − 3 − oxopropan − 1 − oicacid
Functional Groups Abstract IUPAC name
O
(Carboxylic acid) Carboxylic Acid (I.U.=Alkanoic acid)
− C − OH
O
Carbaldehyde (I.U.=Alkanal)
−C − H (Aldehyde)
O
Alkyl Carboxylate (I.U.= Alkyl alkanoate)
−C − O − R (Ester)
O
− C − NH2 (Amide) Carboxamide (I.U.=Alkanamide)

−C  N (Cyanide) Carbonitrile (I.U.= Alkanenitrile)

 1 2 3 O
CH 2 CH CH 2 O C − OH O
Ex.: HO − C C − OH C − OH or H − O − C − CH 2 − CH − CH 2 − C − OH
1 2 3 4 5
O O O
New I.U. → Propane-1,2,3 − tri carboxylic acid Old I.U. → 3 − Carboxy pentane-1,5-dioicacid

1 2 3 O O
2 3 4
CH2 CH CH2
Ex.: or H − C − CH 2 − CH − CH 2 − C − H
1 5
C C C C
O H O H O O
H H
New IUPAC → Propane − 1, 2,3 − tricarbaldehyde Old IUPAC → 3 − Formylpentane-1,5-dial
 1 2 3 O O
CH 2 CH CH 2 or H 2 N − C − CH 2 − CH − CH 2 − C − NH 2
Ex.: 2
1 3 4 5
C C C NH 2 − C
O NH 2 O NH 2 O NH 2
O
New IUPAC → Propane − 1, 2,3 − tricarboxamide Old IUPAC → 3 − Carbamoyl or
3 − Amidopentane − 1,5 − diamide

Correct order of priority

All substituents Alkyne Alkene All functional
−F / − Cl / − Br / − I etc. group
Increasing order of priority
 Some important cases for writing IUPAC names
Case-I When only C-side chains are present on longest C-chain
1 2 3 4 5 6 7
Ex.: 1 CH3 − CH 2 − CH − CH 2 − CH − CH 2 − CH3
Alphabetical CH 2 − CH 3 CH3
order
3 − Ethyl − 5 − methyl heptane
Prefix p suffix
1 2 3 4 5 6 7 8

Ex.: 2 CH3 − CH 2 − CH − CH 2 − CH − CH 2 − CH 2 − CH3

CH3 CH 2 − CH3
I.U. → 5 − Ethyl − 3 − methyloctane
 7 6 5 4 3 CH3 2 1
Ex.3 CH3 − CH 2 − CH − CH 2 − C − CH 2 − CH3
CH 2 − CH3 CH3
I.U. → 5 − Ethyl − 3,3 − dimethyl heptane

1 2 3 4 5 CH3 6 7 8
Ex. 4
CH3 − CH 2 − CH − CH 2 − C − CH 2 − CH 2 − CH 3
CH 2 − CH3 CH3
I.U. → 3 − Ethyl − 5,5 − dimethyloctane
Case II If substituents like –F / -Cl / -Br / -I / -NO2 etc also present along with C-side
chains.
1 2 3 4 5 6
Ex.: CH3 − CH − CH 2 − CH − CH 2 − CH3
Cl CH3
I.U. → 2 − Chloro − 4 − methylhexane
O
Ex.: CH3 − CH − CH − CH − CH 2 − N
O
F Br CH3
I.U. → 3 − Bromo − 4 − fluoro-2-methyl − 1 − nitropentane

F Cl
2 1
Ex.: F − C − C − Br I.U. → 1 − Bromo − 1 − chloro − 2, 2 − difluoroethane

H H Alphabatical order
 1
F Cl 2
L to R →1,1,1, 2, 2
Ex.: F − C −− C − Br R to L →1,1, 2, 2, 2
F H
I.U. → 2 − Bromo − 2 − chloro − 1,1,1 − trifluoroethane
Case III If (=) or () bonds are present along with substituents or C-side chains

Ex.: If double and triple bonds both are present on same position from two ends of longest C-
chain then end > yne
1 2 3 4 5
I.U.  pent − 1 − en − 4 − yne
CH 2 = CH − CH 2 − C  CH
Both are p suffix

Ex.: If double and triple bonds both are present on different position then near so clear (no
priority)
6 5 4 3 2 1
CH3 − CH = CH− CH2 − C  C− H Hex − 4 − en − 1 − yne
Both are p suffix
 1 2 3 4 5
Ex.: CH 2 = CH − CH 2 − CH 2 − CH 2 − Cl

I.U. → 5 − Chloropent − 1 − ene

p suffix
1 2 3 4 5 6
Ex.: CH3 − CH − CH = CH − CH − CH3 I.U. → 2 − Bromo − 5 − methylhex − 3 − ene
Br CH3
Case IV If two or more double bonds (or triple bonds) are present then we have to
write extra alphabet ‘a’ after Alk.
1 2 3 4 5 6 I.U. → Hexa − 1,3,5 − triene
Ex.: CH 2 = CH − CH = CH − CH = CH 2 Complete
p suffix

I.U. → Hex − 1,3,5 − triene (wrong)

1 2 3 4
Ex.: CH  C − C  CH
I.U. → But a − 1,3 − diyne

1 2 3 4
Ex.: CH 2 = C − CH = CH 2
Cl
C.N. → Chloroprene (Artificial rubber)
I.U. → 2 − Chlorobuta − 1,3 − diene
Case V If functional groups are also present along with double / triple bonds or C-side
chains or substituents
Ex.: Succinicacid (C.N.)
Ex.: Acrolein (C.N.) (Acryldehyde) O
3 2 1
CH 2 = CH − C − H CH 2 − C − OH
I.U. → Butane-1,4 − dioicacid
O CH 2 − C − OH
I.U. → Prop − 2 − en −1 − al
s suffix O
Ex.: Maleic acid (C.N.)
Ex.: Malonic acid (C.N.) O
O 1
2 CH − C − OH
C OH
I.U. → Propane − 1,3 − dioicacid
CH 2
p suffix s suffix
3 CH − C − OH
4
C OH O
O I.U. → Cis − But − 2 − ene − 1, 4 − dioicacid
Ex.: Malic acid (C.N.)
O Ex.: Citric Acid (C.N.)
Chiral centre
C − OH O OH O
Carbon atom whose all four
valencies are connected with H −*C − OH *
HO − C − CH 2 − C − CH 2 − C − OH
different groups / atoms 1 2 3 4 5
CH 2 − C − OH
I.U. → 2 − Hydroxybutane COOH
O
−1,4 − dioicacid Old IUPAC → 3 − Carboxy − 3 −
Ex.: Fumaric acid (C.N.) hydroxy pentane − 1,5 − dioic acid
O Alternatively,
2
O CH − C − OH I.U. → Trans − But − 2 − O OH O
1 2 3
1
ene − 1,4 − dioicacid
HO − C − CH 3 H − O − C − CH 2 − C − CH 2 − C − OH
4

Ex.: Tartaric acid (C.N.) COOH

2
O Abstract I.U. → 2 − Hydroxy
1
HO −*CH − C − OH I.U. → 2,3 − Dihydroxy propane − 1,2,3 − tricarboxylicacid
4 butane − 1,4 − dioicacid
HO −*CH − C − OH
3
O
Case − VI If two or more different functional groups are present then we have to follow
priority order of various functional groups.
Ex. : AAE (Aceto aetic ester) or Ex.: Glyoxal (C.N.) Ex.: Methylglyoxal (C.N.)
EAA (Ethyl aceto acetate) O O
O
4 2 1 1 C−H CH3 − C 2
CH3 − C − CH 2 − C − O − CH 2 − CH3
3 2 C−H
O Alkyl H−C 1
I.U. → Ethyl − 3 − ketobutanoate
O O
Ex.: Cinnamic acid (C.N.)
3 2 1 I.U. → Ethane − 1, 2 − dial I.U. → 2 − Ketopropan − 1 − al
C6 H5 − CH = CH − COOH
I.U. → 3 − Phenylprop − 2 − en − 1 − oicacid Ex.: Dimethyl glyoxal(C.N.)
Ex.: Pyruvic acid ( − keto acid)
O O
O O
3 I.U. → Butane − 2,3 − dione
CH3 − C − C − OH CH3 − C − C − CH 3
( − Diketone)
2 1 1 2 3 4
I.U. → 2 − ketopropan − 1 − oicacid
Ex.: Ketene (C.N.)
2 1
CH 2 = C = O
I.U. → Eth − 1 − en − 1 − one or Ethenone

O O
3 2 1
Ex.: CH3 − C − CH − C − C − O − CH 3
5 4
OH C − H Methyl

O
I.U. → Methyl − 2 − formyl
−3 − hydroxy − 4 − keto − pentanoate
 LECTURE – 4
IUPAC of Cyclic Compounds
(Bicyclo & Spirocompounds)
 ORGANIC COMPOUNDS

Open chain Compounds Closed chain or Cyclic or

or Acyclic Compounds Ring compounds

HOMOCYCLIC HETEROCYCLIC

In a ring all In a ring other than

are carbon ‘C’ atoms like N, O,
atoms S etc. are also
present with ‘C’

ALICYCLIC AROMATIC

ALICYCLIC AROMATIC
Naming of Cyclic Compounds (Homocyclic compounds)
Alicyclic Compounds (aliphatic + Cyclic) (Aliphatic compounds = those compounds which are
not aromatic & they can be open chain or close chain)

Monocyclic compounds
Gen. IUPAC :- Cycloalkane

Ex. I.U. → Cyclopropane

Ex. I.U. → Cyclobutane

Ex. I.U. → Cyclopentane

Ex.
I.U. → Cyclohexane
Case – I When no of C-atoms in ring > No of C atoms in C – side chain then
Alkyl Cycloalkane
IUPAC of monocyclic compounds → i.e.Alkylcycloalkane
C − side chain Ring (Parent chain)

1 CH 3
Ex.: 5C 1 Ex.: 6C
2 CH 3
I.U. → 1 − Ethylcyclopentane
I.U. → Cis − 1, 2 − Dimethylcyclohexane

Ex.: I.U.  4 − Cyclopropyl octane

 3
C IUPAC name of monocyclic compound →

A 1 2
Cycloalkyl alkane i.e.cycloalkyl alkane
or C C  
C C Ring Main Chain
I.U. → 1,2 − Dimethylcyclopropane
i.e.prefix (i.e.parent chain)

4 C C 3 2
3 1
or
1 C C 2 Ex.: 5C
4 5
I.U. → 1 − Methylcyclobutane I.U. → 3 − Cyclopentylpentane
Case – II When no. of C-atoms in ring  1
no. of C-atoms in side chain or two or Ex.:
2
more rings directly connected to C-side
I.U. → 1, 2 − Dicyclopropylethane
chain then.
 O O O
Case – III When functional groups like −C − OH, − C − H, − C  N, − C − OR etc.
directly connected to ring then we have to write their abstract IUPAC names
O Br
O 2 1 CN
2
3
Ex.: C − OH Ex.: Alphabeticalorder
1 4
5 6 OH
I.U. → 2 − Ketocyclobutane
carboxylicacid I.U. → 2 − Bromo − 6 − hydroxy
O O Cyclohexanecarbonitrile
HO O
5 C − O − C2 H5 Ex.:
Ex.: H − C C−H
4 1

3 2
Br SH
I.U. → Ethyl − 2 − bromo − 4 − I.U. → 2 − Hydroxy − 5 − mercapto
formylcyclopentanecarboxylate cyclopentanecarbaldehyde
Functional Groups Abstract IUPAC name
O
(Carboxylic acid) Cycloalkane carboxylic Acid (I.U.=Alkanoic acid)
− C − OH
O
Cycloalkane carbaldehyde (I.U.=Alkanal)
−C − H (Aldehyde)
O
Alkyl cycloalkane carboxylate (I.U.= Alkyl alkanoate)
−C − O − R (Ester)
O
− C − NH2 (Amide) Cycloalkane carboxamide (I.U.=Alkanamide)

−C  N (Cyanide) Cycloalkane carbonitrile (I.U.= Alkanenitrile)

 O O O
Case – III When functional groups like − C − OH ; − C − H ; − C  N; − C − OR etc.
present on C-side chain then C-side chain is parent C-chain irrespective of the length of
C-chain. We have to follow simple IUPAC names of functional groups.

2 1 2 1 BICYCLO COMPOUNDS
Ex.: CH 2− C − OH BridgeheadC − (that C atom which is
common for both the rings)
3 4 O
H 2C CH 2
CH
HO CH 2 or
CH
I.U. → 2 − (3 − Hydroxycyclobutyl) H 2C CH 2
ethanoicacid Bridgehead C − 3C − Chain bridge
2C − Chain bridge
2 1 I.U. → Bicyclo [3,2,0] heptane
CH − C  N
Ex.:
CH3 3
Ex.: 2C 2C or
I.U. → 2 − Cyclohexyl propanenitrile
2C Bicyclo [2, 2, 2] octane
Ex.: In case of substituents we will always start numbering from bridge head C & via
longer carbon chain ends to other bridgehead carbon atom. Assign numbering to
shortest carbon bridge in last:
1 1 1
6 Cl 3
7 Cl 3 6 Cl
7 8 2 or 2 8 or 2 8
5 4 4
3 6 7

4 5 5
Wrong Wrong Correct

I.U. → 6 − Chloro bicyclo [3,2,1] octane

1
Ex.: O 2 O
6 7 Bicyclo [2,2,2] octane − 2,6 − dione
8 s suffix
5 3
4
SPIRO COMPOUNDS
They are special type of bicyclo compounds in which only one bridgehead C-atom is present
10 2
5C
1 3 OH
2C 9
Bridge Ex.:
Bridge 8 4
6
7 5
I.U. → Spiro [2,5] octane
I.U. → Bicyclo [4,4,0] decan − 3 − ol
8 1
3
7
Ex.: 2
6
4
5 NO 2

I.U. → 4 − Nitrospiro [2,5] octane

Different bond notation (used in 3D-molecules)
= Simple bond = Atom / Group present in plane of board

= Solid wedge = Atom / Group present above the plane of board

(Towards observer)

= Dashed wedge = Atom / Group present below the plane of

board (Away from observer)
O
C H (S.F.G)
I.U. → 2 − Hydroxypropanal
C OH
H (J.F.G)
CH 3
 LECTURE – 5
IUPAC of Cyclic Compounds
(Aromatic compounds)
 NAMING OF AROMATIC
(HOMOCYCLIC) COMPOUNDS  Naming of benzene or its compounds
R
 Homocyclic  All are C − atoms in ring Side
Ring chain
 Aroma  special odour
Aromatic compounds → All those organic
compounds in which benzene ring is present. I. Naming of Aromatic hydrocarbons
BENZENE (C6 H 6 ) Case I Ring substituted
CH Smallest alkyl group i.e. CH 3 − present
CH CH 
CH 3
CH CH
CH
Two 100% equivalent (same)
resonating structures

  
  6 electrons

 
⎯
→ C.N. → Toluene (C7 H 8 )

are delocalised

I.U. → Toluene or 1 − Methylbenzene

Resonance Hybrid
 C8 H10 Case II − Side chain substituted
CH 3 CH 3 CH 3
Here we have to consider
1
CH 3
1 1 benzene sing as substituent
2 2
2
3
3 CH 3 4
CH 3
or C6 H5 − or Ph − or  −
C.N. = 1, 2 − or C.N. = 1,3 − or
Ortho Xylene meta xylene C.N. = 1,4 − or
I.U. → ortho or I.U. → meta or Para xylene
1, 2 − Dimethyl 1,3 − Dimethyl I.U. → Para or Phenyl radical
benzene benzene 1,4 − Dimethyl
benzene
2 1
Disubstituted benzene → o− | m− | p −
CH − CH 3 Parent chain
CH 3 (irrespective of the no.of
1
2 CH3 C-atoms)
6 3

I.U. → 2 − Phenylpropane
CH 3 5 4
3 CH 3
C.N. → Isopropylbenzene (or cumene)
C.N. → Mesitylene
I.U. → 1,3,5 − Trimethylbenzene
 II Naming of organic compounds in which − OH group is present
Case − I Ring substitued
O−H
sp2
I.U. → Phenol (Antiseptic)i.e.Phene + ol = Phenol
(Old nameof benzene = Phene)

We have 3 categories
Monohydric phenol (one − OH group present on benzene)
O−H
O−H OH 1
1 2 CH 3 1

3
4
CH 3 CH 3
C.N. → o − Cresol C.N. → m − Cresol C.N. → p − Cresol
I.U. → 2 − or o − Methylphenol I.U. → 3 − or m − Methylphenol I.U. → 4 − or p − Methylphenol
Dihydric phenol (Two − OH groups)
O−H
O−H O−H 1
1
OH

4 OH
3 OH
O−H
C.N. → Catechol C.N. → Resorcinol C.N. → Quinol
I.U. → Benzene − 1, 2 − diol I.U. → Benzene − 1,3 − diol I.U. → Benzene − 1, 4 − diol

Trihydric phenol (In which three − OH groups)

O−H O−H O−H
1 1 OH
2 OH 2 1 OH
3 3
OH 4 HO 5 OH
OH
C.N. → Pyragallol C.N. → Hydroxyquinol C.N. → Phloroglucinol
I.U. → Benzene − 1, 2,3 − triol I.U. → Benzene − 1, 2, 4 − triol I.U. → Benzene − 1,3,5 − triol
Case II → Side chain substituted
2 1
CH 2 − CH 2 − OH Aromatic alcohol

sp3

I.U. → 2 − Phenyl ethan − 1 − ol

prefix
CH 2 − H CH 2 −
−H
Note : Toluene (C7 H8 ) ⎯⎯ →
Benzylic − C
(directly connected
to benzene)
Benzyl radical
(C 6 H 5 − CH 2 − )
−H
C C
−H
or (C6 H5 − C−) ⎯⎯ H
C.N. → Benzoradical CN → Benzal radical
(C6 H5 − CH )
 CH 2 − OH O
C.N. → Benzyl alcohol
C C − O − CH3
3
(sp ) I.U. → 1 − Phenyl methanol  Alkyl

Case III Other functional groups I.U. → Methyl benzoate

containing compounds
(a) Ring substituted CN
H C
CH O 
C=O
 or C6 H 5 − C − H
I.U. → Benzonitrile
Benzal I.U. → Benzaldehyde

Br
2
O 3 CN
O 1 (SFG)
C C − OH
 or C6 H 5 − C − OH
PROBLEM : 4
6
5
Benzo I.U. → Benzoic acid O−H
I.U. → 2 − Bromo − 5 − hydroxybenzonitrile
Prefix
PROBLEM : PROBLEM :
O NH 2
1 C−H
C.N. → Salicaldehyde P aromatic amine
I.U. → 2 − Hydroxybenzaldehyde I.U. → Aniline
2 O−H
PROBLEM :
PROBLEM :
OH O
O
V/s H−O−C−O−H
1 C − OH
C.N. → Salicylic acid Carbonic acid
Carbolic acid
I.U. → 2 − Hydroxybenzoicacid
2 OH PROBLEM : O −CH 3
C.N. = Anisole
PROBLEM : I.U. → Methoxybenzene
O NH − CH 3
PROBLEM :
C − CH3 C.N.or I.U. → Acetyl + phenyl + ketone
Acetyl  Acetophenone or 1 − Phenylethanone
s aromatic amine
Ketone I.U. → N-Methylaniline
 Hetero cyclic compounds
O − CH 2 − CH 3
PROBLEM : Aromatic Alicyclic
Aromatic (heterocyclic)compounds
C.N. → Phenetole I.U. → Ethoxybenzene

(b) SIDE CHAIN SUBSTITUTED

O N
3 2 N | O
CH 2 − CH 2 − C − H H
1 Pyridine Furan
Pyrrole
(C5H 5 N)
I.U. → 3 − Phenylpropan − 1 − al
Alicyclic (Heterocyclic) Compounds
O  Which are not aromatic
2
CH 2 − C − OH
Tetrahydrofuran ( T.H.F.)
I.U. → 2 − Phenylethanoic acid O
 Congratulations!
You have taken a step closer to
your Goal!