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IUPAC NOMENCLATURE EXERCISES IN ORGANIC CHEMISTRY

Propose IUPAC names for the following compounds

Note: Key with possible explanation is given at the end.

M
C2H5
C2H 5

O
1) OR CH CH2
H3C CH CH3

I.C
CH3

N
CH3

EM A
AD
CH3 CH3

H
H3C CH CH CH3
2)
CH D
OR CH CH CH2
DI R
CH3 H2C
CH2
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CH3

CH3
W A
W TY

H3C CH2 CH CH3

CH CH CH2
3) OR
CH3 H2 C CH3
W I

CH
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CH3

CH3 CH3
TP V

H3 C CH CH2 CH2 CH
4) OR CH2 CH CH2 CH2 CH3

CH3

CH3
HT

H3C
C CH2 CH3
5) OR H3C
CH CH2

CH2
H3C

CH3

H3C CH CH3
CH CH2
6) OR CH2 CH2 CH CH2 CH2
H3C CH2 CH2 CH CH2 CH3

CH2
H3C
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7) 8)

9) 10)

M
O
I.C
N
11) 12)

EM A
AD
H
CH D
DI R
.A VA

13) 14)

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W A
W TY

15) 16)
W I
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TP V

17) 18)
HT

19) 20)

C
21) 22)

23) 24)
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25) 26)

27) 28)

29) 30)

M
O
KEY WITH EXPLANATION

I.C
N
EM A
C2H5

AD
H
3,4-Dimethylhexane and not 2-Ethyl-3-methylpentane
1)
CH3
CH D
DI R
Explanation:
* This is the common mistake observed. The longest chain is NOT always expected to be
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arranged linearly. The parent chain may be represented zigzag. The condition is the carbons in
the chain must be continuous. In this case, longest chain contains six carbons continuously as
W A

shown below.
W TY

2 1 2 1
C2H 5 CH2 -CH3
3 4 5 5
W I

3 4
6 6
:// .AD

OR
CH3 CH3
TP V

2)
2,3,5-Trimethyl-4-propylheptane

Explanation:
HT

* If chains of equal length are competing for selection as parent chain in a saturated
branched acyclic hydrocarbon, then the choice goes to the chain which has the greatest
number of side chains.

3)
2,5-Dimethyl-4-(2-methylpropyl)heptane
or
4-Isobutyl-2,5-dimethylheptane

Explanation:
* In this case, The chain whose side chains have the lowest-numbered locants is taken as
the main chain.
* Note the two versions. Isobutyl radical is also a valid name and it can also be named as 2-
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methylpropyl.
* Following names may be used for the given unsubstituted radicals only.
H3C H3C

Isopropyl CH Isopentyl CH CH2

H3C H3C CH2

H3C CH3

Isobutyl CH CH2 Neopentyl H3C C CH2

H3C CH3

M
CH3
CH3
H2C

O
sec-Butyl tert-Pentyl H3C CH2 C
CH

I.C
N
CH3
H3C

EM A
AD
CH3

H
H3C

tert-Butyl H3C
CH D
C Isohexyl CH CH2
DI R
CH3 H3C CH2 CH2
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W A

4)
2,7,8-Trimethyldecane and not 3,4,9-Trimethyldecane
W TY

even though
3+4+9 = 16 --- least sum
W I
:// .AD

whereas
2+7+8 = 17 --- first locant is least
TP V

Explanation
* When series of locants containing the same number of terms are compared term by term,
that series is "lowest" which contains the lowest number on the occasion of the first differ-
ence.
* Actually the so called “Least Sum Rule” is the special case of above “Rule of First Differ-
ence”. And incidentally, in most of the simple cases we still use “Least Sum Rule”. But this
HT

becomes tedious when there are more than two substituents and where the actual rule will
come to the surface. (If you don’t use “least sum rule” neglect this statement.)

5)
3-Ethyl-2,2-dimethylhexane

Explanation:
* If two or more side chains of different nature are present, they are cited in alphabetical order.
* In case of simple radicals, they are alphabetized based on the first letter in the name of simple
radical without multiplying prefixes.
For example, compare ‘e’ in ethyl with ‘m’ methyl, and not ‘e’ in ethyl with ‘d’ in dimethyl.
BUT CONSIDER THE NEXT PROBLEM.
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6)

6-(1,2-Dimethylbutyl)-5-ethylundecane

Explanation:
* The name of a complex radical is considered to begin with the first letter of its complete
name.
* In this case, “dimethyl” is included in the radical name (Note: “di”does not indicate two
methylbutyl side chains).
* Hence dimethylbutyl (as complete single substituent) is alphabetized under "d".

M
O
7)

I.C
3-Ethyl-4-methylhexane

N
EM A
AD
Explanation:

H
* If two or more side chains are in equivalent positions, the one to be assigned the lower
CH D
number is that cited first in the name.
* Previously, the less complex side chain is assigned the least number, which is discarded now.
DI R
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8)
4-Ethyl-3-methylheptane
W A
W TY

Explanation:
* In this case, ethyl and methyl groups are not at equivalent positions. Hence according to
W I

“Rule of First Difference”, methyl is given the lowest number.

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9)
TP V

7-(1-methylbutyl)-9-(2-methylbutyl)pentadecane

Explanation:
* In this case the names of complex radicals are composed of identical words. Hence priority
is given to that radical which contains the lowest locant at the first cited point of difference in
HT

the radical.

10)
5,5-Bis(1,2-dimethylpropyl)nonane
OR
5,5-Bis-1',2'-dimethylpropyl)nonane

Explanation:
* Multiplying prefixes like bis-, tris-, tetrakis-, pentakis- etc., are used to indicate more than
one identical side chain which contains terms like bi-, tri-, tetra- etc., in its name.
* The side chain may be enclosed in parentheses
or
carbon atoms in the side chains may be indicated by primed numbers.
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11) 4,6-Diisopropylnonane
OR
4,6-Di(propan-2-yl)nonane

Explanation:
* Note the use of “propan-2-yl” for isopropyl radical.

12)

M
5-tert-Butyl-6-isobutyldecane

O
I.C
N
EM A
Explanation:

AD
H
* The prefixes - “tert” or “sec” are not taken into consideration for deriving alphabetical
priorities. But “iso” is considered to be the part of radical name and important in deciding
CH D
alphabetical priority.
DI R
* In this case, tert-Butyl is alphabetized under “B” whereas isobutyl under “i”
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13)
W A

5-tert-Butyl-6-sec-butyldecane
W TY

Explanation:
W I
:// .AD

* tert-Butyl group is given priority over sec-butyl group. (Why?)

14) (3E)-7-Methyloct-3-ene
TP V

Explanation:
* Double bond must be given priority (and hence lowest number) over “alkyl” groups.
* Only the lower locant of the double bond ( i.e., 3) is cited as the locants of double bond differ
by unity (i.e., 3,4).
* It is in ‘E’(Entgegen) geometrical configuration. The groups with higher priority are on the
HT

opposite sides of double bond.

2
1 H

H
2 1

* But the following is in ‘Z’(Zusammen) configuration i.e., groups with higher priorities are
on the same side of double bond.
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2
H
2
H
(3Z)-7-Methyloct-3-ene

1
1

Additional information:
E-Z Notation:
Following procedure can be adopted while arriving at the stereochemistry around the double

M
bond and can be denoted by E or Z descriptors. (Remember, if any of the doubly bonded
carbon is attached to two similar groups, then there is no need of giving E-Z descriptors.)

O
I.C
* Determine the higher priority group on each end of the double bond. If the higher priority

N
groups are:

EM A
on opposite sides of double bond: E (entgegen = opposite)

AD
H
on the same side of double bond: Z (zusammen = together)

CH D
The priorities are assigned by following Cahn-Ingold-Prelog sequence rules.
DI R
* Rank the atoms directly attached to the olefinic carbon according to their atomic number.
.A VA

High priority is given to the atom with higher atomic number.

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* In case of different isotopes of same element, then higher priority is given to the isotope with
higher atomic mass. (Eg., D>H, C13>C12)
W A

* If the atoms are still identical, examine the next atoms along the chain until a “first point of
W TY

difference” is found. This is done by making a list of atoms linked directly to the atom. Each
list is arranged in order of decreasing atomic number. Then the higher priority is given to the
W I

list which contain atom with higher atomic number at first point of difference.
:// .AD

Eg., Examine the lists of atoms directly linked to the highlighted carbons in the following
compound, (2Z)-2-tert-Butyl-3-methylpent-2-en-1-ol.
TP V

C,H,H O,H,H

H3C *CH *
CH
2 2 OH

C C
C,C,C
*
H3C C* CH3
H,H,H H3C CH3
HT

* Multiple bonds are counted as multiples of that same atom i.e., each  - bond is treated as if
it were another  - bond to that type of atom.
Eg.,
C C

* C* C CH3
C C CH3 is equivalent to
C C
C,C,C
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O O C

C* is equivalent to C* CH3

CH3 O
O,O,C

15) (2E,4E)-3-Methylhexa-2,4-diene

Explanation:
* It is a diene. The positions of two double bonds are indicated by 2,4. At each double bond
the configurations are indicated by 2E,4E.

M
* Starting from either side of the chain, the double bonds are getting same numbers. Hence

O
the carbons on the main chain are numbered such that methyl group is given the least

I.C
number.

N
EM A
AD
16)
(4E)-4-Methylhept-4-en-2-yne

H
Explanation: CH D
DI R
* The triple bond is given the lowest number.
* Another common mistake observed is, students name this compound as (4E)-4-
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Methylhept-3-en-5-yne, which is wrong. Remember the ‘Rule of first point of difference’.
In this case, the carbons are counted such that triple bond gets least number. However
W A

consider the next problem.

W TY

17)
(2Z)-4-Methylhept-2-en-5-yne
W I
:// .AD

Explanation:
* Double bond is given the lowest number when both double and triple bonds are at equiva-
lent positions.
TP V

18)

(3Z)-3,4-Diethylhexa-1,3-dien-5-yne
HT

Explanation:
* When two chains of equal length are competing, then the chain with maximum number of
double and triple bonds is selected as main chain.
* Observe the notation (3Z). There is no need to assign E-Z descriptor for first double
bond.
* In this case also, double bond is given more priority while numbering the chain.
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19)
Ethenyl group(also named as vinyl group)

(4Z)-4-Ethenyl-5-ethynyloct-4-ene

Ethynyl group

Explanation:
* In this case, longest chain contains eight carbons and it should be taken as the parent
chain irrespective of whether it contains maximum number of unsaturations or not.

M
* Selection of chain containing maximum number of unsaturated bonds as main chain (old

O
IUPAC), even though there is a longer chain containing less number of double or triple

I.C
bonds, is not followed now.

N
EM A
Additional information:

AD
H
* The names of univalent radicals derived from unsaturated acyclic hydrocarbons have the
endings “-enyl”, “-ynyl”, “-dienyl”, “-diynyl” etc., and the positions of double and triple
CH D
bonds must be indicated where ever necessary.
DI R
H 2C CH vinyl or ethenyl
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CH allyl or prop-2-en-1-yl
W A

H2C CH2
W TY

CH
prop-1-en-1-yl
W I

H3C CH
:// .AD

isopropenyl
C
TP V

or prop-1-en-2-yl
H3C CH2 or 1-methylvinyl

HC C Ethynyl
HT

HC C CH2 Prop-2-yn-1-yl

H 3C C C Prop-1-yn-1-yl

3-methylidene-5-(prop-1-yn-1-yl)decane
20)

Explanation:
* The names of divalent radicals, formed by removing two hydrogens from a carbon atom
of acyclic hydrocarbon end with “-idene”.
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H 2C methylidene or methylene

CH
H3C
Ethylidene

ethenylidene
H2C C or
vinylidene

propan-1-ylidene

M
CH2
H3C CH or
propylidene

O
I.C
N
H3C
propan-2-ylidene

EM A
AD
C or

H
H3C
Isopropylidene

CH D
DI R
4-ethenylideneheptane
.A VA

C or

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21)
4-vinyledeneheptane
W A

Note: It is a cumulene. The carbon shown is “sp” hybridized.

W TY

22) Hexylcyclopentane
W I
:// .AD

or
1-Cyclopentylhexane
TP V

Explanation:
* In the first name, cyclopentane is given more priority, eventhough the straight chain
contains more carbons, and taken as root word. This is according to the rule -“cycles are
senior to acycles”.

* In the second case, hexane is taken as root word as it contains more number of carbons
HT

than cyclopentane. This type of naming was actually suggested in 1979 recommendations
and can be stated as follows.

“a hydrocarbon containing a small cyclic nucleus attached to a long chain is generally

named as a derivative of the acyclic hydrocarbon; and a hydrocarbon containing a small
group attached to a large cyclic nucleus is generally named as a derivative of the cyclic
hydrocarbon.”

* Most of the older textbooks follow the second convention.

23)
1-ethyl-2-methylcyclohexane
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24)
ethenylcyclobutane

25) methylidenecyclohexane

1-ethenyl-3-ethylcyclopentane
26)

M
O
I.C
N
What about ?

EM A
AD
H
It is (3Z)-1-ethenyl-3-ethylidenecyclopentane

CH D
DI R
27) (1E)-prop-1-en-1-ylcyclopropane
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W A

28) cyclopentene
W TY
W I
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29) cyclopenta-1,3-diene
TP V

2 10
3 1 9
30) (1E,3Z,5E,7Z,9Z)-cyclodeca-1,3,5,7,9-pentaene
4 8
5 6 7
HT
HT
TP V
:// .AD
W I
W TY
W A
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CH D
H
EM A
AD N
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