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Part 4
Nomenclature
(1) Common system – It depends upon source, properties etc.
Ex- Urea (NH2CONH2) – First obtained from the Urine.
Formic acid (HCOOH) – Obtained by distillation of Formica (Latin Formica = red ant)
Acetic acid (CH3COOH) – Component of Acetum (vinegar)
(2). IUPAC system for naming organic compounds :–
Rule 1 - Selection of main chain
Longest continuous carbon chain containing principal functional groups and multiple bonds. This is called main
chain while all the other carbon atoms which are not included in the main chain are called side chain or
substituents
CH2– CH3
CH3 CH CH CH2 – CH3 Side chain
CH2 – CH2 – CH3 Main chain
Side chain
If two chains contain equal number of carbon then main chain is that which contains more number of side chain
C
C C C C – C – C
Main chain (+3-side chain)
C C C
If number of side chains is also same then that will be main chain having its substituent at
lower number.
If all above conditions are same then select alphabetical order
Rule – 2 Numbering of main chain .
Numbering is done from that side of the main chain having its substituent at lower number (lowest set of locants)
C
1 2 3 4 5 6 Correct 1 2 3 4 5 6 2 + 2 + 5 = 9 Correct
C–C–C–C–C–C C–C–C–C–C–C
6 5 4 3 2 1 Incorrect 6 5 4 3 2 1 2 + 5 + 5 = 12 incorrect
C C
C
If position of substituent is same from both side of the main chain, then numbering is done from
alphabetical order 1 2 3 4 5 6 7 3-ethyl, 5-methyl correct
C–C–C–C–C–C–C Alphabetical order
7 6 5 4 3 2 1 5-ethyl, 3-methyl incorrect
C C
C
If alphabets are also same then prefer lower number of substituent of the complex substituent
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Rule 3 – 2° prefix +1° prefix + root word + 1° suffix + 2° suffix
Root word – It is depends upon the number of carbon atom in main chain as:
No. of
Carbon
C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C20 Cn
in main
chain
Root meth. eth. prop. but pent hex hept oct non dec undec dodec tridec icos alk
word
1° prefix – when main chain is a ring then 1° prefix is cyclo –
1° suffix – It is related to C – C bond
For C – C single bond 1° suffix is ane
For C = C double bond 1° suffix is ene
For C C triple bond 1° suffix is yne
Priority order of functional group and their 2° suffix and 2° prefix
Sl. No. Functional group Name of the class 2 suffix 2 Prefix
# –COO– Carboxylate –oate/carboxylate* carboxylato
1 –COOH Carboxylic acid –oic acid/carboxylic acid* Carboxy
2 –SO3H Sulfonic acid –sulfonic acid Sulfo
3 (R–CO)2O Anhydride –oic anhydride
4 –COOR Ester Alkylalkanoate/ alkylcarboxylate* Alkoxycarbonyl
5 COX carbonyl halide alknanoyl halide/ carbonyl halide* Halo carbonyl
6 CONH2 Amide –amide/ carboxamide* Carbamoyl
7 CN Nitrile –nitrile/ carbonitrile* Cyano
8 CHO Aldehyde –al/ carbaldehyde* Oxo/formyl
9 >C=O Ketone –one oxo/keto
10 OH alcohols ol hydroxy
11 –SH Thioalcohol –thiol Mercapto
12 –NH2 Amines –amine Amino
13 –X Halo
14 –NO2 Nitro
15 –OR Alkoxy
16 –R Alkyl
17 –NO Nitroso
* Represents carbon containing principal functional groups and its carbon is not the part of main chain
Note: (1) Following prefixes are considered for alphabetization:
(a) iso , neo (b) di, tri, tetra when represents the name of complex radical are considered for alphabetization
(2) Following are not considered for alphabetization (a) di, tri, tetra for simple radicals (when represent the number of
radicals ). (b) Sec, tert, bis , tris are not considered for alphabetization
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Note
(1) If 1° suffix started with consonant then extra ‘a’ is added in root word
ex. CH2 = CH – CH = CH2 1, 3- butadiene
CH C – C CH 1, 3- butadiyne
(2) Substituents are written as
Number of position in main chain – name of substituent
(3) If 2° suffix started with vowel or y then 1° suffix – e + 2° suffix
CH3 – CH – CH2 – COOH
|
Cl
2° prefix +1° prefix + root word + 1° suffix + 2° suffix
3-chloro + + but + ane + oic acid
= 3-chlorobutanoic acid
Nomenclature of substituents:
1. For multi substituents select the alphabetical order with position
6 5 4 3 2 1
CH3 – CH – CH – CH – CH – COOH
NO2 Br Cl CH3
4-Bromo-3-chloro-2-methyl-5-nitro-hexanoic acid
2. For same type of multi substituents like 2, 3, 4, 5, 6, 7, 8……..etc. di, tri, tetra, penta, hexa, hepta, octa etc used.
6 5 4 3 2 1
CH3 – CH – CH – CH – CH – COOH
CH3 CH3 Cl CH3
3-chloro-2, 4, 5-trimethyl hexanoic acid
3. di, tri, tetra, penta, hexa, hepta, octa etc of the complex substituent used as alphabetical order
For example,
CH3 CH3
4 3 2 1
CH3CH2 CH CH CH2CH3
13 12 11 10 9 8 7 6 5 4 3 2 1
CH3CH2CH2CH2CH2CH2 CH CH2 CH CH2CH2CH2CH3
7-(1,2-Dimethylbutyl)5ethyltridecane
Note Note
It may be noted here that ‘dimethylbutyl’ group as a complete substituent is alphabetised under ‘d’ and as such
is cited before ‘e’ of ethyl group.
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4. When the names of two complex substituents are same, then priority of citation is given to those substituents
which have the lowest locants number of complex substituents. For example,
CH3
1 2 3 4
CH2 CH CH2CH3
CH3 CH2 CH2 CH2 CH2 CH CH CH2 CH2 CH2 CH2 CH2 CH3
1 2 3 4 5 6 7 8 9 10 11 12 13
CH CH2CH2 CH3
1 2 3 4
CH3
6-(1-Methylbutyl)7(2methyl butyl) tridecane
Note Note
It may be noted here that ‘1-methylbutyl’ group is given priority of citation over ‘2-methylbutyl’ group because
the locants 1 comes before 2.
Nomenclature of substituted cyclic compound
1. If the ring contains more or equal number of carbon atoms than the alkyl group attached to it, it is named as a
derivative of cycloalkane and the alkyl group is treated as a substituent group, otherwise it is name as a
derivative of alkane and the cycloalkyl group is considered as substituent group. For example,
1 2 3 4
CH3 CH CH2 CH3 CH2CH2CH2CH2CH3 CH3 CH2 CH CH2 CH3
but-2 - yl cyclohexane Pent-1-yl cyclopentane 3-Cyclobutyl pentane
2. Among the ring or chain which contain main functional group that will be main chain and other will be
substituted group.
3 2 1 4 3 2 1
CH2 CH = CH2 CH = CH COCH3
3-Cyclopropylprop-1-ene 4-Cyclohexylbut-3-en-2-one
3 2 1
CH3 – CH – CH2OH 5 6
3 2 1
1
2 5
CH3
4 1 CH2CH2COOH
3 2
3 4
2-(Cyclopent-3-enyl) propan-1-ol 3-(4-Methylcyclohex-2-enyl) propanoic acid
3. If, however, the alicyclic ring and the side chain contain the same functional group, the compound is named as a
derivative of the side chain of the ring according as the side chain or the ring contains higher number of carbon
atoms. For example,
OH
OH OHC 3 2
1 CH2CHCH2CH3 7 6–2 1
6 2 1 2 3 4 CH2 – [CH2]5 – CHO
1
5 3
4
7-(3-Formylcyclopentyl) heptanal
2-(2-Hydroxybutyl) cylcohexan-1-ol
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4. If a compound contains an alicyclic ring directly linked to the benzene ring, it is named as a derivative of
benzene, i.e., the compound having lowest state of hydrogenation. For example,
2 3
1 1
NO2
4
2 5 6
CH3
Cyclohexylbenzene
1-(2-Methylcyclohexyl)-4-nitrobenzene
5. If two ring-directly attached with chain then chain behaves as main chain
2 1 1 3
CH2 CH2 CH2
2
Dicyclopropylmethane 1-cyclobutyl 2-cyclo 1,3-Dicyclohexylpropane
propyl ethane
