IUPAC Nomenclature Exercises in Organic Chemistry

1
Prepared by V. Aditya vardhan adichemadi(at)gmail.com WARANGAL

Updated on 22nd January, 2010
If you want to get recent update of this file please visit
http://www.adichemistry.com
visit http://www.adichemistry.com
M
IUPAC NOMENCLATURE EXERCISES IN ORGANIC CHEMISTRY
CO
Propose IUPAC names for the following compounds
Y.
IS N
Note: Key with possible explanation is given at the end.
TR
EM HA
C2H5
C2H 5
1)
CH3
CH RDOR
H3C
CH
CH
CH3
CH2
CH3
DI VA
CH3 CH3
W YA
H3C CH CH CH3
2) OR CH CH CH2
CH3 H2C
W IT
CH2
.A
CH3
//W .AD
CH3
P: V
H3C CH2 CH CH3

CH CH CH2
3) OR
CH3 H2 C CH3
CH
CH3
CH3 CH3
TT
H3 C CH CH2 CH2 CH
4) OR CH2 CH CH2 CH2 CH3
H
CH3
CH3
H3C
C CH2 CH3
5) OR H3C
CH CH2
CH2
H3C
2
CH3
H3C CH CH3
CH CH2
6) OR CH2 CH2 CH CH2 CH2
H3C CH2 CH2 CH CH2 CH3
CH2
H3C
M
7) 8)
CO
Y.
IS N
TR
EM HA
9) 10)
CH RD
DI VA
W YA
11) 12)
W IT
.A
//W .AD
P: V
13) 14)
15) 16)
TT
17) 18)
19) 20)
3
C
21) 22)
23) 24)
M
CO
25) 26)
Y.
IS N
TR
EM HA
27) 28)
29)
CH RD 30)
DI VA
KEY WITH EXPLANATION

W YA
W IT
C2H5
3,4-Dimethylhexane and not 2-Ethyl-3-methylpentane
.A
1)
//W .AD
CH3
Explanation:
P: V
* This is the common mistake observed. The longest chain is NOT always expected to be
arranged straight. 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
shown below.
2 1 2 1
C2H 5 CH2 -CH3
TT
3 4 5 5
3 4
6 6
OR
CH3 CH3
H
2)
2,3,5-Trimethyl-4-propylheptane
Explanation:
* 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.
4
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.
M
* Note the two versions. Isobutyl radical is also a valid name and it can also be named as 2-
methylpropyl.
CO
* Following names may be used for the given unsubstituted radicals only.
H3C H3C
Y.
IS N
Isopropyl CH Isopentyl CH CH2
TR
EM HA
H3C H3C CH2
H3C CH3
Isobutyl
H3C
CH RD
CH CH2 Neopentyl H3C C
CH3
CH2
DI VA
CH3
CH3
W YA
H2C
sec-Butyl tert-Pentyl H3C CH2 C
CH
W IT
CH3
H3C
.A
//W .AD
CH3 H3C
tert-Butyl H3C C Isohexyl CH CH2

P: V
CH3 H3C CH2 CH2
4)
2,7,8-Trimethyldecane and not 3,4,9-Trimethyldecane
TT
even though
3+4+9 = 16 --- least sum
H
whereas
2+7+8 = 17 --- first locant is least
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
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
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.
M
For example, compare ‘e’ in ethyl with ‘m’ methyl, and not ‘e’ in ethyl with ‘d’ in dimethyl.
BUT CONSIDER THE NEXT PROBLEM.
CO
6)
Y.
IS N
6-(1,2-Dimethylbutyl)-5-ethylundecane
TR
EM HA
Explanation:
CH RD
* The name of a complex radical is considered to begin with the first letter of its complete
name.
DI VA
* In this case, “dimethyl” is included in the radical name (Note: “di”does not indicate two
methylbutyl side chains).
W YA
* Hence dimethylbutyl (as complete single substituent) is alphabetized under "d".
7)
W IT
3-Ethyl-4-methylhexane
.A
//W .AD
Explanation:
* If two or more side chains are in equivalent positions, the one to be assigned the lower
P: V
number is that cited first in the name.

* Previously, the less complex side chain is assigned the least number, which is discarded now.
8)
4-Ethyl-3-methylheptane
TT
Explanation:
H
* In this case, ethyl and methyl groups are not at equivalent positions. Hence according to
“Rule of First Difference”, methyl is given the lowest number.
9)
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
the radical.
6
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
M
one identical side chain which contains terms like bi-, tri-, tetra- etc., in its name.
* The side chain may be enclosed in parentheses
CO
or
carbon atoms in the side chains may be indicated by primed numbers.
Y.
IS N
TR
EM HA
11) 4,6-Diisopropylnonane
OR
4,6-Di(propan-2-yl)nonane
CH RD
DI VA
Explanation:
* Note the use of “propan-2-yl” for isopropyl radical.
W YA
12)
W IT
5-tert-Butyl-6-isobutyldecane
.A
//W .AD
P: V
Explanation:
* 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
alphabetical priority.
* In this case, tert-Butyl is alphabetized under “B” whereas isobutyl under “i”
TT
13)
5-tert-Butyl-6-sec-butyldecane
H
Explanation:
* tert-Butyl group is given priority over sec-butyl group. (Why?)
14) (3E)-7-Methyloct-3-ene
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
opposite sides of double bond.
7
2
1 H
H
2 1
* But the following is in ‘Z’(Zusammen) configuration i.e., groups with higher priorities are
M
on the same side of double bond.
CO
2
H
2
Y.
H
IS N
(3Z)-7-Methyloct-3-ene
TR
EM HA
1
1
CH RD
Additional information:
E-Z Notation:
DI VA
Following procedure can be adopted while arriving at the stereochemistry around the double
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.)
W YA
* Determine the higher priority group on each end of the double bond. If the higher priority
W IT
groups are:
.A
on opposite sides of double bond: E (entgegen = opposite)

//W .AD
on the same side of double bond: Z (zusammen = together)

P: V
The priorities are assigned by following Cahn-Ingold-Prelog sequence rules.

* Rank the atoms directly attached to the olefinic carbon according to their atomic number.
High priority is given to the atom with higher atomic number.
* 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)
* If the atoms are still identical, examine the next atoms along the chain until a “first point of
TT
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
list which contain atom with higher atomic number at first point of difference.
H
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.
C,H,H O,H,H
H3C *CH *
CH
2 2 OH
C C
C,C,C
*
H3
C C* CH3
H,H,H H3C CH3
* 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.,
8
C C
* C* C CH3
C C CH3 is equivalent to
C C
C,C,C
O O C
is equivalent to C*
M
C* CH3
CH3
CO
O
O,O,C
Y.
IS N
TR
15) (2E,4E)-3-Methylhexa-2,4-diene
EM HA
Explanation:
* It is a diene. The positions of two double bonds are indicated by 2,4. At each double bond
CH RD
the configurations are indicated by 2E,4E.
* Starting from either side of the chain, the double bonds are getting same numbers. Hence
DI VA
the carbons on the main chain are numbered such that methyl group is given the least
number.
W YA
16)
(4E)-4-Methylhept-4-en-2-yne
W IT
Explanation:
.A
//W .AD
* The triple bond is given the lowest number.

* Another common mistake observed is, students name this compound as (4E)-4-
Methylhept-3-en-5-yne, which is wrong. Remember the ‘Rule of first point of difference’.
P: V
In this case, the carbons are counted such that triple bond gets least number. However
consider the next problem.
17)
(2Z)-4-Methylhept-2-en-5-yne
Explanation:
TT
* Double bond is given the lowest number when both double and triple bonds are at equiva-
lent positions.
H
18)
(3Z)-3,4-Diethylhexa-1,3-dien-5-yne
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.
9
19)
Ethenyl group(also named as vinyl group)
(4Z)-4-Ethenyl-5-ethynyloct-4-ene
Ethynyl group
M
Explanation:
CO
* 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.
Y.
* Selection of chain containing maximum number of unsaturated bonds as main chain (old
IS N
IUPAC), even though there is a longer chain containing less number of double or triple
TR
EM HA
bonds, is not followed now.
Additional information:
CH RD
* 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
DI VA
bonds must be indicated where ever necessary.
H 2C CH vinyl or ethenyl
W YA
CH allyl or prop-2-en-1-yl
W IT
H2C CH2
.A
//W .AD
CH
H3C CH
prop-1-en-1-yl
P: V
isopropenyl
C or prop-1-en-2-yl
H3C CH2 or 1-methylvinyl
HC C Ethynyl
TT
HC C CH2 Prop-2-yn-1-yl
H
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”.
10
H 2C methylidene or methylene
CH
H3C
Ethylidene
ethenylidene
H2C C or
vinylidene
M
CO
CH2
propan-1-ylidene
H3C CH or
Y.
IS N
propylidene
TR
EM HA
H3C
propan-2-ylidene
CH RD
C or
H3C
Isopropylidene
DI VA
4-ethenylideneheptane
C or
21)
W YA
4-vinyledeneheptane
W IT
Note: It is a cumulene. The carbon shown is “sp” hybridized.

.A
//W .AD
22) Hexylcyclopentane
or
P: V
1-Cyclopentylhexane
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”.
TT
* In the second case, hexane is taken as root word as it contains more number of carbons
H
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
11
24)
ethenylcyclobutane
25) methylidenecyclohexane
M
1-ethenyl-3-ethylcyclopentane
CO
26)
Y.
IS N
TR
EM HA
What about ?
CH RD
It is (3Z)-1-ethenyl-3-ethylidenecyclopentane
DI VA
27) (1E)-prop-1-en-1-ylcyclopropane
W YA
W IT
28) cyclopentene
.A
//W .AD
P: V
29) cyclopenta-1,3-diene
2 10
3 1 9
30) (1E,3Z,5E,7Z,9Z)-cyclodeca-1,3,5,7,9-pentaene
4 8
5 6 7
TT

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1

Prepared by V. Aditya vardhan adichemadi(at)gmail.com WARANGAL

If you want to get recent update of this file please visit

H3C CH2 CH CH3

KEY WITH EXPLANATION

tert-Butyl H3C C Isohexyl CH CH2

CH3 H3C CH2 CH2

* Hence dimethylbutyl (as complete single substituent) is alphabetized under "d".

number is that cited first in the name.

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

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

The priorities are assigned by following Cahn-Ingold-Prelog sequence rules.

* The triple bond is given the lowest number.

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

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

* Most of the older textbooks follow the second convention.

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