IUPAC Nomenclature Exercises in Organic Chemistry

1
Prepared by V. Aditya vardhan adichemadi(at)gmail.com WARANGAL
Updated on 22nd January, 2010
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Propose IUPAC names for the following compounds Note: Key with possible explanation is given at the end.
C2H 5
C2H5 CH
1)
2)
3)
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4)
5)
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OR
CH2 H3C CH CH3
IUPAC NOMENCLATURE EXERCISES IN ORGANIC CHEMISTRY
CH3
CH3
CH3 CH
CH3 CH
H3C
CH3
OR
CH
CH
CH2
CH3
H2C
CH2 CH3
CH3 CH
H3C
CH2
CH3
OR
CH
CH
CH2
CH3
H2 C
CH3
CH
CH3
CH3 CH
CH3 CH
OR
H3 C
CH2
CH2
CH2
CH
CH2
CH2
CH3
CH3
H3C C
CH3 CH2 CH CH2 CH3
OR
H3C CH2 H3C
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Prepared by V. Aditya vardhan adichemadi(at)gmail.com
CH3 H3C CH CH CH2 CH2 CH CH2 H3C CH2 CH2 CH3 CH3
WARANGAL
6)
OR
H3C
CH2 CH2
CH2 CH2
CH
9)
11)
13)
15)
17)
19)
10) 12) 14) 16) 18) 20)
7)
8)
3
Prepared by V. Aditya vardhan
C
adichemadi(at)gmail.com
WARANGAL
21)
22)
25)
27)
29)
C2H5
1)
Explanation: * 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
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.
26) 28) 30) KEY WITH EXPLANATION
3,4-Dimethylhexane and not 2-Ethyl-3-methylpentane CH3
C2H 5
3 4 5
CH2 -CH3
4 5
OR
CH3
CH3
23)
24)
4
3)
2,5-Dimethyl-4-(2-methylpropyl)heptane or 4-Isobutyl-2,5-dimethylheptane
Isopropyl
Isobutyl
sec-Butyl
tert-Butyl
4)
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 difference. * Actually the so called Least Sum Rule is the special case of above Rule of First Difference. 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 dont use least sum rule neglect this statement.)
H3C H3C CH
Isopentyl
CH
CH2
H3C H3C
H3C
CH2
CH3 C
CH
CH2
Neopentyl
H3C
CH2
H3C
CH3
CH3
CH3 C
H2C
CH
tert-Pentyl
H3C
CH2
H3C
CH3
CH3 C
H3C
H3C
Isohexyl
CH
CH2
CH3
H3C
CH2 CH2
2,7,8-Trimethyldecane
and not 3,4,9-Trimethyldecane even though 3+4+9 = 16 --- least sum
whereas 2+7+8 = 17 --- first locant is least
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 2methylpropyl. * Following names may be used for the given unsubstituted radicals only.
5
5)
3-Ethyl-2,2-dimethylhexane
6)
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: didoes not indicate two methylbutyl side chains). * Hence dimethylbutyl (as complete single substituent) is alphabetized under "d". 7)
Explanation: * If two or more side chains are in equivalent positions, the one to be assigned the lower number is that cited first in the name. * Previously, the less complex side chain is assigned the least number, which is discarded now. 8)
Explanation: * 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-(1,2-Dimethylbutyl)-5-ethylundecane
3-Ethyl-4-methylhexane
4-Ethyl-3-methylheptane
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.
6
10)
5,5-Bis(1,2-dimethylpropyl)nonane OR 5,5-Bis-1',2'-dimethylpropyl)nonane
11)
Explanation: * Note the use of propan-2-yl for isopropyl radical. 12)
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
13)
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.
4,6-Diisopropylnonane OR 4,6-Di(propan-2-yl)nonane
5-tert-Butyl-6-isobutyldecane
5-tert-Butyl-6-sec-butyldecane
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.
7
2 1 H
Additional information: E-Z Notation: 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.) * Determine the higher priority group on each end of the double bond. If the higher priority groups are: 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. * 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 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. 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 H3C O,H,H
2
* 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.,
2 H H (3Z)-7-Methyloct-3-ene 1 1
* CH * C
* CH2 OH
C
C H3
* C
H3C
C,C,C CH3 CH3
H,H,H
* But the following is in Z(Zusammen) configuration i.e., groups with higher priorities are on the same side of double bond.
8
C C C C CH3
WARANGAL
* C
CH3
is equivalent to
C* C
C,C,C
O C* CH3 O C CH3
15)
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. * Starting from either side of the chain, the double bonds are getting same numbers. Hence the carbons on the main chain are numbered such that methyl group is given the least number. 16)
Explanation: * The triple bond is given the lowest number. * Another common mistake observed is, students name this compound as (4E)-4Methylhept-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 consider the next problem. 17)
18)
(3Z)-3,4-Diethylhexa-1,3-dien-5-yne
Explanation: * Double bond is given the lowest number when both double and triple bonds are at equivalent positions.
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.
O
O,O,C
(2E,4E)-3-Methylhexa-2,4-diene
(4E)-4-Methylhept-4-en-2-yne
(2Z)-4-Methylhept-2-en-5-yne
is equivalent to
C*
9
19)
Ethenyl group(also named as vinyl group)
(4Z)-4-Ethenyl-5-ethynyloct-4-ene
Additional information: * 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 bonds must be indicated where ever necessary.
H 2C CH
H2C
H3C
H3C
HC
HC
H 3C
20)
Explanation: * The names of divalent radicals, formed by removing two hydrogens from a carbon atom of acyclic hydrocarbon end with -idene.
vinyl or ethenyl
CH
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. * Selection of chain containing maximum number of unsaturated bonds as main chain (old IUPAC), even though there is a longer chain containing less number of double or triple bonds, is not followed now.
allyl or prop-2-en-1-yl
CH2
CH
CH
prop-1-en-1-yl
CH2
isopropenyl or prop-1-en-2-yl or 1-methylvinyl
Ethynyl
CH2
Prop-2-yn-1-yl
Prop-1-yn-1-yl
3-methylidene-5-(prop-1-yn-1-yl)decane
Ethynyl group
10
H 2C
WARANGAL
methylidene or methylene
CH H3C
Ethylidene
H2C
H3C
H3C
H3C
21)
Note: It is a cumulene. The carbon shown is sp hybridized. 22)

Hexylcyclopentane or 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. * In the second case, hexane is taken as root word as it contains more number of carbons 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
CH2 CH
propan-1-ylidene or propylidene
propan-2-ylidene or Isopropylidene
4-ethenylideneheptane or 4-vinyledeneheptane
ethenylidene or vinylidene
11
24)
ethenylcyclobutane
25)
methylidenecyclohexane
26)
What about
It is (3Z)-1-ethenyl-3-ethylidenecyclopentane
27)
28)
29)
30)
4
?
(1E)-prop-1-en-1-ylcyclopropane
cyclopentene cyclopenta-1,3-diene 10 2 1 9 8 (1E,3Z,5E,7Z,9Z)-cyclodeca-1,3,5,7,9-pentaene 5 6 7
1-ethenyl-3-ethylcyclopentane

IUPAC Nomenclature Exercises in Organic Chemistry

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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

IUPAC NOMENCLATURE EXERCISES IN ORGANIC CHEMISTRY

CH3 CH2 CH CH2 CH3

H3C CH2 H3C

and not 3,4,9-Trimethyldecane even though 3+4+9 = 16 --- least sum

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

Explanation: * Note the use of propan-2-yl for isopropyl radical. 12)

C,C,C CH3 CH3

Ethenyl group(also named as vinyl group)

isopropenyl or prop-1-en-2-yl or 1-methylvinyl

Note: It is a cumulene. The carbon shown is sp hybridized. 22)

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