2

Follow me On Instagram
@
arvind.aroraj
3
 4

vdnt.in/medicalv

Link Given in “Description Box”

General Organic
Chemistry L-4
 In this session, we will cover
IUPAC Nomenclature

GOC
Exercise: Nomenclature
L-4

Alkyl substitutents

6
 1.
IUPAC Nomenclature

7
 ORGANIC CHEMISTRY

Millions of organic compounds

How will we identify each compound then?

8
 IUPAC Nomenclature

Systematic method of naming

IUPAC- International Union of Pure and

Applied Chemistry

9
 IUPAC Nomenclature

10
 IUPAC Nomenclature- History

◆ Earlier, organic compounds were assigned names based

on their origin or certain properties.

◆ Example: Citric acid was named so because it is found in

citrus fruits.

◆ These names are called as common names / trivial

names

11
 The IUPAC naming for branched alkanes

12
 Parts of IUPAC name

1o + 2o
Prefix + Word Root +
suffix suffix

Substituents No. of c atoms unsaturation Principle functional

in the parent chain index group

13
 Rules for IUPAC nomenclature

Rule 1: Select the longest continuous chain. It will be

called as the parent chain

14
 Rule 1: Example

C C C C C C C C C
Longest chain ⇒ 8 C
C C C

C C C C C C C C C
Longest chain ⇒ 9 C
C C C

Note:If there is a functional group, it must be part of the

parent chain.
15
 Rule 2:

Assign the number to the carbon atoms of the longest chain

such that the substituent receives the lowest possible number
irrespective of their nature.

1 2 3 4 5 6 7 8 9
C C C C C C C C C
9 8 7 6 5 4 3 2 1
C C C

L – R : 2, 6 R – L : 4, 8

16
 Rule 2: Examples

Example 2 :
1 2 3 4 5 6 6 5 4 3 2 1
C C C C C C C C C C C C Lowest
Locant rule
C C C C C C

17
 Rule 3:

After selecting the longest chain and numbering the carbon atom,
while writing the name of compound the substituent which is
alphabetically 1st should be written first irrespective of its locant.

18
 Rule 3: Examples
1 2 3 4 5 6 7 8 9
C C C C C C C C C
C C C
m e
6 - Ethyl - 2 - methylnonane

Note: Two no’s should be separated by ‘comma’

Number and letters should be separated by ‘hyphen’
First letter capital

19
 Rule 4:
When a molecule contain two or more identical substituents, use
numerical prefix such as di, tri, tetra etc. for two, three, four
substituents respectively, however their initial alphabet shouldn't be
considered for ordering the substituents in the final naming.

20
 Rule 4: Example
m C
1 2 3 4 5 6 7 8
C C C C C C C C C
9 8 7 6 5 4 3 2
C C C
e m
9
L–R:377 R–L:337
1
7 – Ethyl – 3, 3 - dimethylnonane

21
 Rule 5:

If the two substituents are found in equivalent

positions, the lower number is given to the one
coming first in the alphabetical listing.

22
 Rule 5: Example

3-ethyl-6-methyloctane not 6-ethyl-3-methyloctane

23
 2.
Exercise: Nomenclature

24
 Exercise: Nomenclature
CH3 CH CH3
1.
CH3

25
 Exercise: Nomenclature
CH3 CH CH3
1.
CH3

Answer
1 2 3
CH3 CH CH3
1. 2 - Methylpropane
CH3 m

26
 Exercise: Nomenclature

CH2 CH3
2. CH3 CH2 C CH2 C CH3
CH2 CH3

27
 Exercise: Nomenclature
CH2 CH3
2. CH3 CH2 C CH2 C CH3
CH2 CH3

Answer
5 6
CH2 CH3
7C 2 3 4
2. CH3 CH2 C CH2 C CH3
e m
6 C CH2 CH3
1 m

28 2 - Ethyl – 4, 4 – dimethylhex – 1 – ene

 Exercise: Nomenclature

3.

29
 Exercise: Nomenclature

3.

Answer
e
6 2
3. 4 3
7 5 1
m m

4 - Ethyl – 3, 3 – dimethylheptane

30
 Exercise: Nomenclature
4. H3C C C CH2 CH CH3
CH3

31
 Exercise: Nomenclature
4. H3C C C CH2 CH CH3
CH3

Answer
1 2 3 4 5 6
4. H3C C C CH2 CH CH3
CH3 m

5 – Methylhex - 2 - yne

32
 3.
Alkyl Substituents

33
 Alkyl substituents as a complex branches
:
As we know
Alkane – H = Alkyl (R–)
Cn H2n + 2 Cn H2n + 1

34
 Alkyl substituents as a complex branches
:
–H
CH4 CH3 – Methyl
–H
CH3 CH3 CH3 CH2 Ethyl
CH3 CH2 CH3 –H CH CH2 CH2 Propyl
3

CH3 m
2 1
H 3C CH CH3 H 3C CH (1 – methylethyl) Systematic names
isopropyl Head carbon

35
 Naming of alkyl substituents

CH3 CH2 CH2 CH3

CH3 CH2 CH CH3

CH3
H 3C C
CH3

36
 Naming of alkyl substituents
CH3 CH2 CH2 CH3 CH3 CH2 CH2 CH2 butyl

3 2 1
CH3 CH2 CH CH3 (1 – methylpropyl)
m
Sec - butyl

CH3 m
H 3C C (1, 1 – Dimethyl ethyl)
2 1
CH3 m

37
 Points to be remember

Instead of using systematic naming, if we are using sec, tert naming of complex
substituent it is to be remembered that they are to be italicized and
should not be considered for alphabetical ordering.

When iso and neo naming of alkyl group is used

instead of systematic name, their alphabets are
to be considered for ordering

38
 Let’s revise n , iso, neo, sec and tert – alkyl groups :

39
Naming of Alkyl Substituent

Write common and systematic name following alkyl groups :

Alkyl substituent Common name Systematic name

CH3 CH2 CH2 Propyl Propyl

2 1
H 3C CH
isopropyl 1 - methylethyl
CH3
Write common & systematic name of following alkyl groups

Alkyl substituent Common name Systematic name

CH3 CH2 CH2 CH2

H 3C CH2 CH
CH3
CH3
CH3 CH CH2
Write common & systematic name following alkyl groups :
Alkyl substituent Common name Systematic name

C C C C C pentyl pentyl
C C C C
4 3 2
C
1 ― 1 – methylbutyl

C C C C
4 3 2 1 ― 2 – methylbutyl
C
Write common and systematic name following alkyl groups :
Alkyl substituent Common name Systematic name
C
C C C
C
C
C C C
C

C C C
C C
Write common and systematic name following alkyl groups :

Alkyl substituent Common name Systematic name

C
C C C tert-pentyl 1, 1 – dimethylpropyl
3 2 1
C
C
C C C
3 2 1 neo-pentyl 2, 2 – dimethylpropyl
C

3 2 1
C C C
–– 1, 2 – dimethylpropyl
C C
 46

Follow me On Instagram
@
arvind.aroraj
 47

vdnt.in/medicalv

Link Given in “Description Box”

48