IUPAC
IUPAC
CH3 CH CH3
. Isobutane
2) Closed chain or Cyclic compounds : These compounds con-
tain one or more closed chains of atoms. These are further divided
into two types:
a) Homocyclic or carbocyclic compounds: These are the com-
pounds which contain one or more closed chains of carbon atoms
only. They are further subdivided into two types:
i) Alicyclic compounds: These are cyclic compounds and re-
semble aliphatic compounds in their properties e.g. cyclopropane,
cyclohexane etc.
CH2 CH2 CH2
CH2
. CH2 CH2 CH2
. Cyclopropane Cyclobutane
Alicyclic compounds are important compounds as alicyclic rings are
present in a number of natural product e.g. steroids, alkaloids etc..
ii) Aromatic compounds: These are cyclic compounds which
generally contain at least one benzene ring. (benzene ring ring
of six carbon atoms having alternate single and double bonds) e.g.
benzene, naphthalene, phenol etc.
.
. Benzene Naphthalene
b) Heterocyclic compounds: These are cyclic compounds which
contains at least one atom other than carbpon in the ring e.g. fu-
ran, pyridine, thiazole etc.
CH
CH
CH CH CH
CH
O CH CH
CH
N
. Furan Pyridine
————————————————————————————–
Hydrocarbons: Organic compounds containing carbons and hy-
drogen only are known as hydrocarbons. Hydrocarbons are further
divided into two classes: saturated and unsaturated.
Saturated hydrocarbons: The hydrocarbons in which all the
available valencies of carbon are satisfied by hydrogen are known
as saturated hydrocarbons. In saturated hydrocarbons, the car-
bons atoms are joined to each other by a single covalent bond e.g.
alkanes.
Unsaturated hydrocarbons: The hydrocarbons in which the
proportion of hydrogen is less as compared to the available valen-
cies of carbon are known as unsaturated hydrocarbons. Hydrocar-
bons, two carbons atoms are joined to each other by double bond
(alkenes) or a triple bonds(alkynes).
Cp H 3 Cp H Cp H2 Cp H2 Cp Cp H 2 Cp H3
Cs H3 Cs H3
The ‘Cp ’s make the parent chain and the ‘Cs ’ make the substituents.
It may be noted that the longest chain may or may not be straight
but it must be continuous. For example,
. C1 H3 C2 H2 C3 H CH2 CH3
C4 H2 C5 H2 C6 H3
. Correct parent chain indicated by C 1 to C 6
. C1 H3 C2 H2 C3 H C4 H2 C5 H3
(a) C1 H3 C2 H2 C3 H C4 H C5 H3
CH CH3
CH3
CH3
(b)CH3 CH2 C3 H C2 H C1 H3
C4 H CH3
C5 H3
In (a),C 1 to C 5 is the longest chain but only 2 substituents. In
(b), C 1 to C 5 is the longest chain with 3 substituents; so (b) is the
correct parent chain
2. Lowest set of locants: Number the carbon atoms in the par-
ent chain as 1,2, 3.... etc., starting from the end which gives smaller
number to the carbon atoms carrying the substituent. For example,
if S represents a substituent;
S S
C5 C4 C3 C2 C1 C1 C2 C3 C4 C5
. Structure ‘A’ Structure ‘B’
. Correct numbering Wrong numbering.
The numbering of the carbon chain as given in the structure B is
wrong because it gives higher number to the carbon atom carrying
the substituent. The number that indicates the position of the sub-
stituent or side chain is called locant. The position of the locant in
the above structure is 2.
When there are two or more different substituents attached to the
parent chain, then the end of the parent chain which gives lowest
set of the locants is preferred for numbering. This rule is called
lowest set of locants. This means that when two or more dif-
ferent sets of locants are possible, that set of locants which when
compared term by term with other sets, each in order of increasing
magnitude, has the lowest term at the first point of difference. This
rule is used irrespective of the nature of the substituents.
This rule is very simple to apply. We are to compare the position of
substituents term by term. This means that compare the first term,
whichever is lower will get the preference. If both ends have same
position for preference, the first substituent, compare the second,
then third that gives the lower number to carbon will get preference.
Similarly, compare, third term if needed and so on.For example,
CH3 CH3
C6 H3 C5 H2 C4 H2 C3 H C2 H C1 H3
. Set of locants = 2,3 (Correct)
CH3 CH3
C1 H3 C2 H2 C3 H2 C4 H C5 H C6 H3
. Set of locants = 4,5 (Wrong)
CH3 CH2 CH3 CH3
C1 H3 C2 H C3 H2 C4 H C5 H2 C6 H2 C7 H C8 H3
. Set of locants = 2,4,7 (Correct)
CH3 CH2 CH3 CH3
C8 H3 C7 H C6 H2 C5 H C4 H2 C3 H2 C2 H C1 H3
. Set of locants = 2,5,7 (Wrong)
While writing the name of the compound, the position of each sub-
stituent or side chain is indicated by the number of the carbon atom
to which it is attached. The names of the substituents are sepa-
rated from the number indicating their positions by using hyphens.
For example,
CH3
. C5 H3 C4 H2 C3 H2 C2 H C1 H3
. 2-Methylpentane
3. Presence of more than one same substituent: If the same
substituent occurs more than once in the parent chain, it is indi-
cated by the prefixes such as di, tri, tetra, etc. to indicate 2, 3, 4,
etc. same substituents.The positions of each substituent whether
same or different are indicated separately and the numerals dif-
ferent representing their positions are separated by commas. For
example,
CH3
. C1 H3 C2 H C3 C4 H2 C5 h C6 H3
. C5 H3 C4 H3 C3 C2 H C1 H3
CH3 CH3
. 3-Ethyl-2,3-dimethylpentane.
5. Naming different substituents at equivalent positions: If
two different substituents are present at equivalent positions from
the two ends of the chain (two sets of locants are equally possible),
then the numbering of the chain is done in such a way that the sub-
stituent which comes first in the alphabetical order (written first
in the name) gets lower number. For example, in the compound
given below the methyl is at 3rd position if numbering is done from
left to right and ethyl groups is at 3rd position if numbering is done
from right to left.In such a case, the carbon bearing the ethyl group
gets lower position because it is cited first in the name according
to alphabetical order of substituents.Thus,
C7 H3 C6 H2 C5 H C4 H2 C3 H C2 H2 C1 H3
C3 H2 C4 C5 H2 C3 H2 C4 CH2
CH2 CH3 C5 H2 C6 H3
. Correct chain Wrong chain.
It maybe noted that the selected chain may or may not be the
longest chain. But it must contain double or triple bonded atoms.
For example, in the above example, the largest chain containing
double bonded carbon atoms is of five carbon atoms and not of six.
2. While writing the name of the alkene or alkyne, the suffix ‘ane’of
the corresponding alkane is replaced by ‘ene’ or ‘yne’ respectively.
3. If the multiple bond occurs twice in the parent chain, the alkene
and alkyne are called ‘diene’ and ‘diyne’ respectively.
4. The numbering of atoms in parent chain is done in such a way
that the carbon atom containing the double or triple bond gets the
lowest number. For example,
. C1 H3 C2 H C3 H C4 H2 C5 H3
. Pent-2-ene (Not Pent-3-ene)
The position of the double bond may be indicated by any of the
three ways: 2-Pentene or Pent-2-ene or Pentene-2.
5. All the rules for naming the side chains or substituents are then
followed (as in alkanes). For example:
CH3
. C6 H3 C5 C4 H C3 H C2 H C1 H3
CH3 CH3
. 4,5,5-Trimethylhex-2-ene.
Important notes:If the parent chain contains both double and
triple bonds, the following rules should be remembered:
i) The terminal ‘e’ in the name is dropped when it is followed by
the suffix beginning with any vowel or ‘y’. Therefore, the terminal
‘e’ of ene in ‘en-yne’ and a ‘dien-yne’ is dropped because it comes
before ‘y’(of - yne) However, e is not dropped in case of ‘enediyne’
because it comes before d of - diyne.
ii) Numbers as low as possible are given to double bond and triple
bond as a set, even though this may at times give -yne a lower num-
ber than -ene. However, if a choice is there, preference for lower
locants is given to double bond.
iii) These compounds are named as derivatives of alkynes rather
than alkenes.
For example,
i). C5 H C4 C3 H2 C2 H C1 H2
. Pent-1-en-4-yne
In this compound numbering is 1-4 from both sides, then preference
of lower locant for ‘ene’
ii) . C1 H C2 C3 H C4 H C5 H2
. Pent -3-en-1-yne.
The name of this compound cannot be Pent-2-en-4-yne as the low-
est set of locants is is 1, 3 rather than 2, 4.
In the case of cyclic alkenes, the position of double bond is always
given the number 1.
.
CH3
CH3
(2,3-dimethylcyclohex-1-ene; Not 1,6-Dimethylhex-1-ene; )
III Nomenclature of Compounds containing One Func-
tional Group or Secondary Suffix:In naming the organic com-
pounds containing one functional group, the numbering of the atoms
in the parent chain is done in such a manner that the carbon atom
bearing the functional group gets the smallest possible number. All
other rules for naming the side chains or substituents are then fol-
lowed.
1. Select the longest continuous chain containing the carbon atom
having the functional group.
2. The numbering of atoms in the parent chain is done in such a
way that carbon atom bearing the functional group gets the lowest
number.
3. All the rules for naming side chains or substituents are then
followed as discussed in case of alkanes.
The different classes of functional groups including multiple bonded
compounds and the suffix required to name these compounds are
given in the table above.For example,
O
C6 H3 C5 H C4 H2 C3 C2 H2 C1 H3
CH3
. 5-Methylhexa-3-one
It may be noted that the functional group should get the lowest
number even if it violates the lowest set rule. Preference should
be given only to the functional group. If functional groups such as
CHO,COOH,CONH2 ,COOR,COCl,CN are present in the molecule,
the number of parent chain must start from the carbon atom of the
functional group (secondary suffix). The position of the functional
group will always be number 1. The position is normally not indi-
cated in the IUPAC name of the compound.
Example:
CH3
i) CH3 CH2 C2 C3 H2 C4 H3
C1 HO
. 2-Ethyl-2-methylbutanal
5
ii) C H3 C4 C3 C2 H2 C1 HO
. Pent-3-ynal
If a compound contains two same functional groups, the numerical
prefix di, is used before the name of the secondary suffix. In this
case, the terminal e of the primary suffix is retained while writing
the IUPAC name.
OHC CH2 CH2 CHO HOOC CH2 CH2 COOH
. Butanedial Butanedioic acid.
In these structures, the positions of CHO or COOH group are not
indicated because these groups will always be at the terminal po-
sition, having number 1 and last i.e., Butane-1,4-dial or Butane-1,
4-dioic acid.
O O
NC CH2 CH2 CN C5 H3 C4 C3 H2 C2 C1 H3
. Butanedinitrile Pentane-2,4-dione
IV. Nomenclature of Compounds having Functional Groups,
Multiple Bonds, Side Chains, Substituents: If the organic
compound contains a functional group, multiple bond, side chain
or substituent, the order of preference is :
Functional > Double bond> Triplebond > Substituent/
Side chain
Examples:
O
i)C5 H2 C4 H C3 H2 C2 C1 H3
. Pent-4-en-2-one
CH3
ii)C9 H3 C8 H2 C7 H2 C6 H2 C5 H2 C4 H C3 H C2 H CHO
. 2-Methylnon-3-enal
O
iii) C6 H5 C3 H C2 H C1 OH
. 3-Phenyl prop-2-enoic acid
iv)C4 H3 C3 H C2 H CH3
Cl C1 OOH
. 3-Chloro-2-methylbutanoic acid.
Exercise:
Q 1. The ‘Vital force theory’ was proposed by —.
Q 2. How and when was the ‘Vital force theory’ proven wrong?
Q 3. The highest level of catenation is observed in —- elemnt.
Q 4. Which of the folowing statements is wrong?
(i) Organic compounds possess low melting and boiling points.
(ii) Organic compounds exhibit isomerism.
(iii) Organic compounds are obtained only from netural resources.
(iv) Organic compounds can be synthesised in the laboratory.
Q 5. Which of the following is called an unsaturated compound by
definition?
(i) CH3 CH = CH2 (ii) CH3 C ≡ N
O
—————————————————————————————
CH3
2. CH3 CH CH2 CH CH3
CH3 CH3
3. CH3 CH CH2 CH CH2 CH3
CH3 CH2
CH3
CH3
CH3
CH3 CH3
5. CH3 CH CH CH3
CH3
CH2
CH3
7. CH3 CH2 CH CH CH CH3
CH3
CH3
CH2
CH3
CH3
CH2
CH3
Give the IUPAC names for given Alkenes:
1. CH3 − CH = CH2
2. CH3 − CH = CH − CH = CH2
3. CH2 CH CH CH3
CH3
4. CH3 CH2 C C CH3
C3 H7 CH3
5. CH2 C CH2 CH CH2 CH3
CH3 CH3
6. CH3 CH CH CH CH CH CH CH3
CH3
7. CH3 C CH2
8. CH3 C CH CH CH3
CH3 CH3
9. CH2 C CH2 CH2 CH2 CH3
CH3
10. CH2 C CH CH2
CH3
C2 H5
CH3
3. HC ≡C CH CH CH2 CH3
CH3 CH3
CH3 CH3 CH3
4. CH ≡C CH CH CH CH2 CH3
CH3
5. CH ≡C C CH2 CH3
CH3
6. CH3 C≡C CH ≡C C≡C C≡C CH CH2
CH3 CH3
C3 H7 C3 H7
CH3
CH3 CH3
10. CH3 C≡C CH3
Give the structure of the following compounds:
1) 2,3 dimethyl-1-butane 2) 2- methyl- 1- propene
3) 1- propyne 4) 2,3,4-trimethy-l- hexane
5) 3-methyl-2- pentene 6) 3-methyl-1- butyne
7) 4,4,5-trimethy-l,2-hexyne 8) 2,2,3,4-tetramethy-1-pentane
9) 1,4-hexadiene 10) 3-heptyne
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Alkyl halides:
Give the Trivial or common names of following compounds:
1) CH3 Cl 2) C2 H5 Br
3) CH3 CHICH3 4) (CH3 )3 CBr
Give the IUPAC name of following compounds
1) CH3 Cl 2) C2 H5 Br
3) CH3 CHCH3 4) CH3 − CH2 − CH2 − CH2 − Cl
CH3
Cl Cl
H H H H
7) H C C H 8) C C 9) CH3
Cl Cl H Cl CHCl2
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Alcohols/Acids:
Give the common names of the following compounds
1) CH3 OH 2) C2 H5 OH
3) CH3 CH2 CH2 CH2 OH 4) CH3 CH2 CH2 OH
CH3 CH3 CH3
OH OH OH
7) CH3 H7 OH 8) C4 H9 OH
H
OH
H OH
H
CH3 OH CH3
13) CH3 CH C CH2 CH3 14) CH3 CH CH2 CH2 OH
CH3 CH3
19) HCOOH 20) CH3 COOH