Nomenclature of Organic Compounds

Nomenclature of Aliphatic/Acyclic compounds

Line-Angle Formula (Skeletal Structure or Stick Figure):
Very handy for writing organic structures, mostly for cyclic compoounds. Carbon atoms are assumed to be
present wherever two lines meet or a line begins or ends. N, O, X, S (heteroatoms) are shown while C, H are
not shown. H is shown onto a heteroatom.

O CH3 O
C
NH NH CH OH
OH CH
H3C CH
= CH3
C CH3
H3C
CH3

Alkanes
Rule: Longest continuous carbon chain bearing maximum number of branches, numbered in the direction
in which any alkyl branch is met first (Lowest Set of Locant Rules). Name of alkyl branches written first with
alphabetic order followed by Word Root + ane(primary suffix). The first letter of the complex branch is
considered for alphabetic ordering. For simple branch the multiplying prefixes di-, tri-, tetra- are not considered
for alphabetic ordring. Complex branches are multiplied with the prefix bis, tris, tetrakis, pentakis etc. Locants
are separated by commas and no space in between branches and parent alkane. If the set of locants is same
from both side, then the alphabetically senior branch gets the lower locant.

branches + alk + ane

Examples:
Lower Set of Locants Rule:

CH3 CH3
7 5 2 4
8 CH 6 CH2 CH2 1 CH 3 CH2 CH2
4 5
H3C CH CH3 H3C CH CH3
CH CH
3 1 6 8
CH3 CH3
CH2 2 CH3 CH2 7 CH3
CH2 CH2

4-ethyl-6,7-dimethyloctane(wrong) 5-ethyl-2,3-dimethyloctane(correct)

CH3
2 4 6 8 10

1
CH2 3 CH 5 CH2 7 CH2 9 CH3
9 7 5 3 1
H3C CH CH2 CH2 CH
10 8 6 4 2

CH3 CH3
3,4,9-trimethyldecane (wrong) (not lower set: begininng with 3)
2,7,8-trimethyldecane (correct) (Lower set: beginning with 2)

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Same Set of Locants: Alphabetic Serniority:

CH3 3-methyl-4-ethylhexane (wrong)

5 CH2 1
CH2 3 3-ethyl-4-methylhexan (correct)
4 CH 2 CH3
6 2' 4' 6'
H3C CH
3' CH2
1' 5'
CH3

Branching Rule:

CH3 CH3
2 4 6 2 4
1 CH 3 CH2 CH2 7 1 CH 3 CH2 CH2
5 5
H3C CH CH3 H3C CH CH3
CH CH
6
CH3 CH (wrong) CH3 CH (correct)
7

CH3 CH3 CH3 CH3

2,3-dimethyl-5-propan-2-ylheptane(wrong) 5-ethyl-2,3,6-trimethylheptane(correct)
The first one violates the branching rule. In 2nd one, the longest chain has largest number branches attached to it.

8'
7' C H3
H3C CH 3 CH 2 8
2' 6 C H3
4
CH CH CH 7
1' 3 5
CH CH CH
H3C
2
C C H3 C H3
H3 C 1 CH3
CH 3

6-ethyl-2,2,4,5-tetramethyl-3,7-bis(propan-2-yl)octane
N.B: propan-2-yl is a complex branch to be discussed below.
Line Structure of Alkanes:
1
H3C 2 CH3
CH CH3 7
3 5
CH3 CH 4 CH 6 CH2 8

= CH2 CH CH CH3
CH2 CH3
CH3

3,4-diethyl-2,5,6-trimethyloctane
SAQ I. 1: Give the IUPAC names of the following:
CH3
CH2 CH3
H3C CH CH2 CH3 CH CH3
CH CH3
(i) H3C (ii) CH2 (iii) H3C
CH C CH3
CH3
CH2 CH3
CH3
Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

H3C CH3
CH3 CH3 CH3 CH3
CH CH2
H3C C CH3 H3C C C CH3
(iv) H3C CH CH (v) (vi)
CH2 CH2 CH3 CH3 CH3 CH3

(vii) (viii)

SAQ I.2: Give the structural formula of the following compounds.

(i)2,3-dimethylpentane (ii)3-methylhexane (iii)2,2,4-trimethylhexane
(iv)2-methylpropane
SAQ I.3: Some incorrect names are given. Write the structure of alkanes from them. Also give the correct
names.
(i)3-methylbutane (ii)2-ethylpropane (iii)4,5-dimethylhexane

Naming a complex branch:

Latest Rule: Numbering made from one terminal to the other giving lower locant to -yl. When locant of -yl is 1,
then the suffix ‘ane’ is replaced by ‘yl’ and the loacnt 1 is dropped. For example, propyl, butyl, etc instead of
prop-1-yl, but-1-yl.
Simple alkyl groups like methyl, ethyl, propyl, butyl in which the locant of -yl is 1 are called simple branches.
All other alkyl branches containing subbranches of simple alkyl groups like 2-methylpropyl or having locant of
-yl other than 1 like propan-2-yl etc. are considered as complex branches. The first letter of the complex
branches is considered for alphabetic numbering which includes di-, tri-etc. Such branches are multiplied by
the prefixes bis, tris, tetrakis etc.
When locant of ‘yl’ is not 1, then letter ‘e’ of ‘ane’ is replaced by ‘yl’,with the locant of ‘yl’ prefixing it. For
example propan-2-yl etc.
3 2 3 2 1
CH3 CH CH3 CH2 CH2
1
CH3
propyl
propan-2-yl

4 3 2 4 3 2 1
CH3 CH2 CH CH3 CH2 CH2 CH2
1
CH3 butyl
butan-2-yl

1
CH3 CH3
CH3 3 1 3 1
3 2 2
2 CH3 CH CH2 CH3 C CH2
CH3 C
CH3 CH3
2-methylpropyl
2-methylpropan-2-yl 2,2-dimethylpropyl

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Old Rule:
The carbon atom of the alkyl branch directly bonded to the principal carbon chain is numbered 1’ to find the
longest chain. Ultimately prime over the locant is dropped once it is put insidie parenthesis.

CH3
CH3 CH3 2' 1'
CH3 C
CH3 CH CH3 CH2 CH
2' 1' 3' 2' 1' CH3

1-methylethyl 1-methylpropyl 1,1-dimethylethyl

isopropyl(propan-2-yl) sec-butyl(butan-2-yl) tert-butyl(2-methylpropan-2-yl)

CH3 CH3
3' 2' 1'
CH3 C CH2
CH3 CH CH2
3' 2' 1' CH3

2- methylpropyl 2,2-dimethylpropyl
isobutyl neopentyl
2-methylpropyl and 2,2-dimethylpropyl remain the same for both old and new conventions.

N.B: Many text books still use the old convention of naming a complex alkyl branch(1,1-dimethylethyl). The
names like isobutyl, isopropyl, sec-butyl, tert-butyl, neopentyl are also used in some texts in IUPAC naming.
So the student should not take much critically on this aspect. Remember that a structure can have more than
one IUPAC names out of which one is PIN(Preferred IUPAC Name) as per the latest conventions but one
name can have a unique structure.
Two branches having same initial words:
When two groups have same initial words(or letters), the longer branch gets the higher locant. Beween
methyl and methylpropyl the former gets a lower locant.

3' 1'
2 4 2'
10 12
3 5
1 6 7 8
2' 9
1' 3' 11

6-methyl-8-(2-methylpropan-2-yl)-5-(2-methylpropyl)dodecane (latest)
8-(1,1-dimethylethyl)-6-methyl-5-(2-methylpropyl)dodecane (old)
8-(tert-butyl)-5-isobutyl-6-methyldodecane (old)
If you write according to old system, then for complex branch the prefixes di-, tri- are considered for alphabetic
ordering as in the new convention. Using the common names of the alkyl groups, the prefix tert- and sec- are not
considered while the prefixes iso and neo are considered for alphabetic ordering.
3'
1' 2'
2 4
10 12
3 5
1 6 7 8
9 6,6-bis(2,2-dimethylpropyl)dodecane
2' 11
1'

3'

A complex branch has to be multiplied with the prefixes bis, tris etc. (not di, tri etc.)
Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

SHORT REPRESENTATIONS OF SOME COMMON ALKYL GROUPS:

The following abbreviations are used for the alkyl groups written against their names.
methyl Me isobutyl i-Bu
ethyl Et sec-butyl s-Bu
n-propyl n-Pr tert-butyl t-Bu
isopropyl i-Pr n-butyl n-Bu
SAQ I.4: Give the IUPAC names of the following compounds shown in line drawings.

(i) (ii)

(iii) (iv)

(v) (vi)

(vii) (viii)

(Rule for naming compound (viii): When two or more longest chains containing same number of branches
and same set of locants for the branches compete with each other, IUPAC recommends that the
longest chain which contains greatest number of carbon atoms in the branches is correct.

(ix) (ix) (x)

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

(xi) (xii)

(xiii)

SAQ I.5: Draw the line structures for the following molecules.
(i) 5-(2-methylpropy)dodecane (ii) 4-(propan-2-yl)-4-propylnonane
(iii) 5-(butan-2-yl)-5-(propan-2-yl)decane (iv) 4,4-bis-(2-methylpropan-2-yl)heptane
(v) 3-ethyl-6-(5-methylhexan-3-yl)-8-(propan-2-yl)undecane

Answers to SAQs
SAQ I.1 (i) 2,3-dimethylpentane (ii)3-methylpentane
5
CH3
4
CH CH3
3
(iii) H3C C CH3 3,3,4-trimethylpentane(wrong); the set of locants =3,3,4 which is higher
1
2
CH2 CH3

2,3,3-tripmethylpentane(correct) , The set of locants 2,3,3 is lower and is correct..

1
CH3 7 CH3 7
H3C H3C 6
2 6 CH3 CH3
CH CH2 CH CH2
3 1 3 5
5
(iv) H C CH CH
(correct); H3C 2 CH CH (wrong)
3 4 4
CH2 CH2 CH3 CH2 CH2 CH3

The second one is violating the branching rule. In the first, there are more number of branches attached
to the main chain. Count for yourself to verify.
Name: 3-ethyl-2,5-dimethylheptane.
The reverse direction of numbering would have given a higher set of locants: 5-ethyl-3,6-dimethylheptane
which is wrong.

CH3
1 2 3
H3C C CH3
(v) ; 2,2-dimethylpropane (same name if we reverse the numbering)
CH3

CH3 CH3
1 2 3 4
H3C C C CH3
(vi) ; 2,2,3,3-tetramethylbutane(same name on reverse numbering)
CH3 CH3

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

CH3

8 6 4 2

(vii)H3C9 7 5 3
CH3 ; 5-methyl-4-propylnonane (reverse numbering would have given the
1

CH3

set of locants 5,6 which is higher)

(viii) 5-ethyl-6,7-dimethyl-4-propyldecane
(The set of locants are same on either side. Hence lowest locant is given to alphabetically seniormost branch
ethyl by numbering from left to right).
SAQ.I. 2: While writing the structure of a compound from its name, first look to the word root of the parent
alkane. In this case it is alk(e.g pent-, hex-, but- etc.). First draw a carbon chain containing the required
number of carbon atoms in straight chain. Let us take the first bit.
(i) The parent alkane is pentane. So let us first draw: C-C-C-C-C. Then number them from one end to the
other end. Attach the substituents(branches) at the appropriate carbon atoms.
1 2 3 4 5
C C C C C

CH3 CH3
Then attach the required number of hydrogen atoms to each carbon atom of the main chain bearing in
mind that the valency of carbon is 4.
1 2 3 4 5
CH3 CH CH CH2 CH3

CH3 CH3
2 3 4 5 6

CH3 CH2 CH CH2 CH2 CH3

(ii)
CH3

CH3
1 2 3
1 2 3 4 5 6
CH3 CH CH 3
CH3 C CH2 CH CH2 CH3
(iii) (iv)
CH3 CH 3
CH3
SAQ I. 3:
1 2
4 3 2 1 CH3 CH CH3
CH3 CH2 CH CH3 (2-methylbutane) 3
(i) (ii) CH2 (2-methylbutane)
CH3 4
CH3

6 5 4 3 2 1
CH3 CH2 CH CH CH CH3
(iii) (2,3-dimethylhexane)
CH 3 CH 3

SAQ I.4:
(i) 4-ethyl-2-methyl-5,6-dipropylnonane
(ii) 3,6,8-triethyl-2,4-dimethyl-6-propylundecane
(iii) 5-(pentan-3-yl)decane (PIN); 5-(1-ethylpropyl)decane
(iv) 6-(3-methylbutyl)-5-(2-methylpropyl)undecane
(v) 2,3,5-trimethyl-4-propylheptane

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

(vi) 2,5-dimethyl-4-(2-methylpropyl)heptane
(vii) 7-(2-methylhexan-2-yl)-7- (2-methylpentan-2-yl)tridecane (PIN)
OR 7-(1,1-dimethylbutyl)-7-(1,1-dimethylpentyl)tridecane
(viii) 7,7-bis(2,4-dimethylhexyl)-3-ethyl-5,9,11-trimethyltridecane
(ix) 6-ethyl-2,4-dimethyl-5-(2-methylpropyl)-3-(propan-2-yl)octane (PIN)
OR 6-ethyl-2,4-dimethyl-3-(1-methylethyl)-5-(2-methylpropyl)octane
(x) 2,3-dimethyl-5-(propan-2-yl)octane(PIN) OR 2,3-dimethyl-5-(1-methlethyl)octane
(xi) 3,6-dimethyl-5-(3-methylbutan-2-yl)-7-(propan-2-yl)decane (PIN)
5-(1,2-dimethylpropyl)-3,6-dimethyl-7-(1-methlethyl)decane
(xii) 4-(2,2-dimethylpropyl)-9-ethyl-2,2-dimethyl-6,6-bis(2-methylpropan-2-yl)undecane(PIN)
6,6-bis(1,1-dimethylethyl)-4-(2,2-dimethylpropyl)-9-ethyl-2,2-dimethylundecane
(xiii) 6-methyl-5-(3-methylbutan-2-yl)decane(PIN) OR 5-(1,2-dimethylpropyl)-6-methyldecane

SAQ I.5:
H3C CH3
CH3 H3C
H3C

CH3
(i) (ii)
CH3
CH3
CH3

CH3
H3C CH3
H3C CH3
CH3

(iii)H3C (iv)H3C CH3

H3C CH3
H3C CH3
CH3

H3C CH3
CH3

H3C

CH3
(v)H 3C

CH3
CH3

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

ALKENES & ALKYNES

Rules
Old:
C C / C C should be a part of principal carbon chain even if it may not be the longest chain.
Locant of ‘ene’/ ‘yne’ should be least. In case of tally, the LSL(lower set of locants) rule for branches come into
force.
Branches + Word Root + primary suffix(ene/yne)
1
CH2
5
4
2 (2-ethyl-3-methylpent-1-ene)
H3C C 3
CH2 5
4 2
CH2 CH (not 4-ethyl-3-methylpent-4-ene)
3 CH3
1
CH3

CH3
2 4 6
CH 3 (2-methylhex-3-ene)
CH CH
1 5 3 3 5 1
H3C CH CH2 (not 5-methylhex-3-ene
6 4 2

CH3
1 2 3 4
HC C C CH3
3,3-dimethylbut-1-yne (not 2,2-dimethylbut-3-yne)
CH3

6
CH3 CH3
5
4 3 2 1 2,2,5-trimethylhex-3-yne
CH C C C CH3 NOT 2,5,5-trimethylhex-3-yne
CH3 CH3

SAQ Write the IUPAC names from the following line structures.

(i) (ii)

Answer:
(i) 6-(butan-2-yl)-3-(propan-2-yl)-2,2,7-trimethylnon-4-yne
(ii) 3-ethyl-8-methyldec-5-yne(ethyl gets precedence over methyl due to alphabetical seniority of
the former)
NEW:
Longest continuous carbon chain to be taken as parent hydrocarbon. This may or may not include C C /

C C . If C C / C C is not included, the parent becomes alkane. In such case, the branch containing

C C / C C are written along with other alkyl branch in alphabetic order.

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Naming branch containing C C /C C :

Monvalent alkenyl and alkynyl group:
The letter ‘e’ of ene/yne is replaced by ‘yl’. It becomes alkenyl or alkynyl. Note that ‘en/yn’ has its locant and
‘yl’ also has its locant. If the locant of ‘yl’ is 1, then it is dropped. According to new convention, the branch is
numbered from one terminal to another like a complex alkyl group. However, the old rule is still followed by some
text books in that the carbon atom bonded to the longest chain is numbered 1. See the following examples.
1
3 2 1 3 2 1
CH2 CH CH2 CH CH2 CH3 CH CH
ethenyl or vinyl prop-2-en-1-yl or allyl prop-1-en-1-yl
or prop-2-enyl or prop-1-enyl
3 2 5 4 3 2
CH3 C CH3 CH CH CH
1 CH2 1 CH3
prop-1-en-2-yl but-3-en-2-yl
(1-methylethenyl) (1-methylbut-2-enyl)

HC C HC C CH2 H3C C C
ethynyl prop-2-yn-1-yl prop-1-yn-1-yl
or prop-2-ynyl or prop-1-ynyl
Bivalent alkylidene group:
If =C- is directly bonded to the longest chain, then the group is bivalent. In that case, a suffix ‘idene’ is to be
used with the respective ‘alkyl’ group.
alkyl + idene = alkylidene
alkyl - alkylidene
CH 3 - (methyl group) CH 2 = (methylidene group)
CH3-CH2-(ethyl) CH3CH= (ethylidene)
CH3-CH2-CH2-(propyl) CH3-CH2-CH= (propylidene)
H3 C H3 C
CH C
(propan-2-yl/isopropyl (propan-2-ylidene/isopropylidene)
H3 C H3 C

Naming bivalent group contianing one more C C / C C :

alkenyl + idene = alkenylidene alkynyl + idene = Alkynylidene

H3 C CH CH CH (but-2-enyl) H3 C CH CH CH (but-2-enylidene)

CH C CH (prop-2-ynylidene)
SAQ : Write the names of the following groups.

H3 C
CH3 CH2 CH C CH
CH CH 2 CH
(i) (ii) CH3
(iii) H3C C C CH
H3 C

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

H3 C CH3
H3 C C CH CH C C CH2
(iv) CH 3 (v) (vi) H2 C C CH CH2 (vii)CH2=C=
H3 C CH3

(viii) CH3CH(CH3)CH(CH3)CH= (ix) CH3CH2C(CH3)=

Answer:

(i) 3-methylbutylidene (ii)2-methylpent-2-enylidene

(iii)but-2-ynylidene (iv)2-methylprop-1-enyl
(v)4-methylpent-2-ynyl (vi)2,3-dimethylbut-3-enyl
(vii)ethenylidene(vinylidene) (viii) 2,3-dimethylbutylidene
(ix) butan-2-ylidene

Naming Alkenes and Alkynes according new rule:

8 6 4 2

H 3C 7 5 3 CH 3
CH 3 9 1

1
2 4 6 8
2
H 3C 3 5 7 CH 3
1 9
CH
3
CH 2

2-methyl-7-methylidenenonane(new name) 5-(prop-2-ynyl)nonane( new name)

2-ethyl-7-methyloct-1-ene(old name) 4-butyloct-1-yne(old name)
SAQ : Write the names of names of the following alkenes and alkynes on the basis of the new rules.
Compare the names with those obtained by using old rules.

CH 3 CH3

CH3
CH3
H 3C CH 3 H3C
(i) (ii)
CH 3 CH3
CH 3 H3C

H 3C

CH 3

(iii)
CH
CH 3

Answer:
(i) 3,4-diethyl-5-methylhept-2-ene(same according both the rules as the C=C bond is included in
the longest chain)
(ii) 4-ethyl-2,7-dimethyl-5-propylidenenonane(new);
5-ethyl-7-methyl-4-(2-methylbutyl)oct-3-ene(old)
(iii) 3-ethyl-5-ethynyloctane(new); 5-ethyl-3-propylhept-1-yne(old)

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Haloalkanes(Alkyl Halides)
Rule:
The halo group(-X) may or may not be directly bonded to the longest carbon chain. If it is not directly bonded,
then it is part of a complex alkyl group with a halo subbranch. The naming is done just like any alkane. Halo
bearing group competes with other alkyl groups for alphabetical seniority.
1 2 3 4 5
H3C CH CH CH2 CH3
: 3-bromo-2-methylpentane(not 3-bromo-4-methylpentane)
CH3 Br

Br
H3C

6 4

H3C 5 3
7 CH3
CH3
2
H3C CH3
1

4-(2-bromoethyl)-3-ethyl-2,5,6-trimethylheptane

In the above example, Br- is a part of a complex group bromoethyl.

SAQ : Give the IUPAC names from the following line structures

Cl CH3 Br

(i) (ii) (iii)

Cl H3C CH3
I

Asnwer:
(i) 4-(butan-2-yl)-3-chloro-5-methylheptane (ii)4-ethyl-5-iodomethyl-2-methylheptane
(iii) 2-bromo-6-chloro-4-methylheptane

Functional Groups having Secondary Suffixes:

(Naming multifunctional compounds)

The following table gives the functional groups and their suffixes which are used after primary suffix.

Branches(Prefixes)+Word Root + primary suffix + secondary suffix

Word Root: meth(1), eth(2), prop(3), but(4), pent(5), hex(6), hept(7), oct(8), non(9), dec(10),
undec(11), dodec(12), tridec(13), tetradec(14), pentadec(15), hexadec(16), heptadec(17),..
icos(20), henicos(21), docos(22), tricos(23), tetracos(24), pentacos(25).... triacont(30),
hentriacont(31), dotriacont(32), tritriacont(33), tetratriacont(34)...... tetracont(40),
hentetracont(41),dotetracont(42), tritetracont(43)..........pentacont(50),
henpentacont(51),dopentacont(52)......., hexacont(60), henhexacont(61), dohexacont(62).....,
heptacont(70), henheptacont(71), doheptacont(72)...... octacont(80), henoctacont(81),
dooctacont(82)....... nonacont(90), hennonacont(91), dononacont(92)...... hect(100), henihect(101),
dohect(102), trihect(103), tetrahect(104).....decahect(110), undecahect(111),
dodecahect(112)........icosahect(120).....

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Primary suffix : ane/ene/yne

1. If there will be at least one C=C or C C , then primary suffix ‘ane’ is not used. In stead ‘ene’ or

‘yne’ is used. If there are more than one C=C or C C , then di-, tri- etc. are used as prefix to ‘ene’, ‘yne’.
In such case, the letter ‘a’ is suffixed to the Word Root (alk) to maka it alka (eg buta, penta, hexa etc.). For
example buta-1,3-diene(not but-1,3-diene).
2. C=C or C C can be used as primary suffix as ‘ene’ or ‘yne’ along with the secondary suffix of the
seniormost functional groups. They can also be used in a branch with the name alkenyl, alkynyl, alkylidene,
alkenylidene or alkynylidene etc.
3. The following table gives the functional groups with decreasing priority order for which secondary suffix
is used. These are called Type C groups which can both be used as suffix or as prefix(branches).

Type C functional Groups:

Name of group structure prefix suffix

O -oic acid
carboxylic acid C OH
carboxy (carboxylic acid)
sulfonic acid -SO3H sulfo sulfonic acid
O O
acid anhydride C O C - -oic anhydride

O -oate
ester C OR'
alkoxycarbonyl (carboxylate)

O -oyl halide
acid halide C X
halocarbonyl (carbonyl halide)

O
acid amide -amide
C NH2 aminocarbonyl (carboxamide)

nitrile C N cyano
-nitrile
(carbonitrile)
O oxo -al
aldehyde C H (formyl) (carbaldehyde)
O
ketone C oxo -one

alcohol -OH hydroxy -ol

thiol -SH sulfanyl/mercapto -thiol
amines -NH2/-NHR/-NR2 amino -amine
________________________________________________________________________________
Deletion of ‘e’: If the secondary suffix begins with any vowel such as ‘a, y, i, o, u’ then the letter ‘e’ to
be deleted from prmary suffix ane/ene/yne. For example butanol, pentanone, but pentanenitrile.
(NB: For acquainting with the IUPAC naming compounds containing single functional group,
please refer e-Concepts in Chemistry for Junior Level: Nomenclature Chapter-II)

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Rules:
* The LONGEST carbon chain bearing the highest priority functional (type C) group should also bear
maximum number of other type C groups. Such group(s) cannot be ignored or be excluded from the longest
chain. Such a chain may exclude C=C or C C if required, if they are not part of the LONGEST chain
containing maximum number of type C groups.
Conclusion: The longest chain bearing the highest priority group may or may not include other functional
groups or C=C/ C C . Betwen any typc C group and C=C/ C C , the former is preferred.

* The one having highest priority among such groups will make the secondary suffix. In other words
the parent compound will be named after this. Other such groups will be used as branches(prefixes). For
-OH it is hydroxy, for (-C=O) it is oxo and so one. Look to the prefix column for this. The suffix names
which are written inside parenthesis below their respective first names are used only when such functional
group is outside the principal carbon chain. For example, if -COOH remains within the principal chain, i.e
the carboxyl carbon is counted as no. 1, then the secondary suffix ‘oic acid’ is used. If -COOH remains
outside the carbon chain, then ‘carboxylic acid’ is used. As a prefix also if -CHO(aldehyde) group remains
outside the carbon chain, then ‘formyl’ is used otherwise ‘oxo’ is used.
Groups which are used only as substitutents(Prefix): Type A groups
Such groups do not have any priority order. All such groups obey LSL rule.
Name of the group General formula
alkyl R-
alkoxy RO-
alkylsulfanyl(alkylthio) RS-
halo X-
nitro NO 2 -
alkenyl R CH CH

alkynyl R C C
phenyl C6H5-
cycloalkyl cyclopropyl, cyclobutyl etc.

(Note that C=C and C C are called Type B functional groups which are used as primary suffix(ene/yne)
* Since -COOH and derivatives of -COOH and -CHO are terminal functional groups, the one which
has the highest priority among them always gets no. 1 locant.
* When –CN is a lower priority group in a molecule, it is never taken inside the principal carbon chain.
It is always used as prifix(cyano). Cyanide carbon is never counted in such case.

* In polyene/enynes C=C and C C enjoy the same priority. However in case of tally, ‘ene’ gets
the precedence.
CH 3
O Cl O

7 5 3 1

H 3C 6 4 2 OH
8

O OH

5-chloro-2-cyano-4-hydroxy-7-methoxy-6-oxooct-3-en-1-oic acid OR
5-chloro-2-cyano-4-hydroxy-7-methoxy-6-oxooct-3-enoic acid

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

(locant 1- for terminal functional groups appearing in secondary suffix is deleted).

OH
Cl

H 4 2 O CH3
5 3 1

O OH O

ethyl 4-chloro-3-hydroxy-2-(hydroxymethyl)-5-oxopentanoate

(note that for aldehyde group, we used the prefix ‘oxo’ as it is a part of the carbon chain. For ketones too
we shall use ‘oxo’.

HO 6
5 NH 2

4 2 OH
3 1

O
O H
6-amino-5-hydroxy-4-(2-oxoethyl)hexanoic acid

The longest chain containing more number of functional groups is chosen irrespective their priorities.

NH2 O

O 6 1 OH
H
O O 5 4 3 2
6 1
5 4 3 2
NH2 O NH2

NH2 H
2-amino-5-methyl-6-oxohex-3-ynamide 2,6-diamino-5-formyl-6-oxohex-3-ynoic acid

In the 2nd case above, amide is senior to aldehyde, hence amide carbon was included in the principal chain.
Since -CHO is now excluded from main chain, the prefix ‘formyl’ has been used. Note that for amide group,
we used two suffixes, one for -C=O(oxo) and other other for -NH2(amino).
functional group two prefixes used
amide both amino and oxo (not aminocarbonyl)
acid chloride both chloro and oxo (not chlorocarbonyl)
ester both alkoxy and oxo (not alkoxycarbonyl)

H O
O
4 2 OH
6
2
3 1
5 4
3 1 Cl CH3 O

O O
2-ethyl-4-formylhexanoyl chloride 4-methoxy-2-methyl-4-oxobutanoic acid

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

SO3 H O O
2
H 3C 3 5 CH3
1 3 4
1 2 4 6 7
OCH3

4-methoxy-3-methyl-4-oxobutane-2-sulfonic acid Cl Br OH

4-bromo-2-chloro-6-hydroxyhept-5-en-3-one

1'
2 I
OH 5 2' 4'
H2N 3 1 3
6 4 2 3'
3-aminopropan-1-ol
(not 3-hydroxypropan-1-amine 1
CN OH

2-(3-hydroxybutan-2-yl)-3-iodo-4-methylhexanenitrile

Br
CH3 CH2 O

7 5 3 1

Cl 2-bromo-5-chlorohexane H3C 6 4 2 OH
8
2-chloro-5-bromohexane(wrong)

7-methyl-5-methylideneoctanoic acid
old: 5-(2-methylpropyl)hex-5-enoic acid)
CH2
CH2
HO 6 4 2 OH
H3C 4 2 O CH3 7 5 3
6 1
5 3 1
CH3 O
O

propan-2-yl 2-(prop-2-enylidene)hex-4-enoate 7-hydroxy-4-methylideneheptanoic acid

old: 1-methylethyl 2-(but-2-enyl)penta-2,4-dienoate old: 4-(3-hydroxypropyl)pent-4-enoic acid
O

5 3 1

4 2
O CHO 1CN
H3 C OH
6 7 5 4 3
6 2
COOEt
CH3 C CH C C CH CH2 CH3
4-(ethoxycarbonyl)hexanoic acid
2-ethyl-5-formyl-6-oxohept-3-ynenitrile

4 6 4
2
3 2 1 OH 5 3 1 O
N C
CN O
O
4-cyano-2-methylbutanoic acid sec-butyl 5-cyano-2-methylpentanoate

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

1
4 2 CN COOEt
3 1 OH 2
4
NC 3
O 5

4-cyano-2-methylbutanoic acid Ethyl 4-cyano-2-ethyl-3-methylpentanoate

CH3 CH3
CH
O
3 O
CHO O 7C 5
4 2 1
EtO OH
6
COOEt

ethyl 6-methyl-7-oxo-4-(propan-2-yloxy)hept-4-enoate 7-ethoxy-7-oxoheptanoic acid

O O
3 O 3 5 7
5 CH3 C1
C 6 2 6 8
EtO 4 1 CH O
OH 2 4
CH3 C
7 8 O NH2

6-(ethoxycarbonyl)oct-7-enoic acid propan-2-yl 6-(aminocarbonyl)octanoate

Polyenes/Polyyenes/enyes:
In this case, longest chain is the key. That chain can bear C=C, C C , then its preferred. Such longest
chain should bear maximum number of multple bonds, but not at the cost of chain length.

1 3 5 9 7 3 1
11 5
6 10 8 6 4 2
2 4

(I) (II)
3-methylhex a-1,4-diene 5-ethyl-7,9-dimethylundeca-4,6-diene

6 4
7 5
1 4 2
2
2 3 5 3 1
1 4
3 6

(IV) (V)
(III)
4-isopropyl-6-methyl-3-propylhept-5-en-1-yne but-1-en-3-yne hexa-1,3-dien-5-yne

[Please read 4-(propan-2yl) for 4-isopropyl in (III) of the above structures and put it after 6-methyl. Isopropyl
can be used but it is now not PIN].

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

7
5 3
2 6 4 2
8 4
7 5 3
9 6 1 1

6-ethyl-3,7-dimethyl-4-methylidenenon-2-ene 4-(ethenyl)hep-5-en-1-yne
old: 2-(2-ethyl-3-methylpentyl)-3-methylpenta-1,3-diene
(In the last structure ‘e’ has been deleted from ‘ene’ as ‘y’ is facing it. ‘en’ is always written first even though
its locant is higher)
H3C
6
5
7
2 4 5
CH2
4 2'
1 3 1' 3' 6 7
2 3

H2C 8 9 CH
1 10

4-(prop-1-enyl)hepta-1,4-diene 7-ethenyl-5-ethylidenedec-1-en-9-yne
2

CH 3 CH3
1

H3C 6 4 6 8
7
5 7 CH3
5 4 3 9

2 CH3 CH2
1
H2C
H3C
CH

3-ethenyl-3-ethynyl-2-methylheptane 5-(prop-2-ynylidene)-4-vinylnona-2,7-diene
Old: 4-(2-methylpropyl)-4-propylpent-1-en-4-yne 4-(but-2-enyl)-5-ethenylocta-3,6-dien-1-yne

Compounds containg idential functional groups:

In such case, the secondary suffix is prefixed with di-, tri- etc. For example, diol, trione, dial etc. In such case
the ‘e’ of primary suffix is not dropped.
Rule: The principal chain should bear maximum number functional groups.

Br
1 3 5 OH OH OH
3
OH OH 2 4 6 2 4 OH
CH2 CH CH2
CH2 CH2 OH 1
OH OH
ethane-1,2-diol propane-1,2,3-trio 2-buty lbutane-1,4-dio
(et hylene glycol)
5-bromohexane-2,4-diol (glycerol)

OH

1
2
2 4 6 CH3
8
5 3 CH3 H3 C 3 5 7
4 1
H 3C
6

OH OH NH2 NH2 CH3

3-(1-hydroxyethyl)hexane-1,4-diol

7-methyloctane-3,5-diamine

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

CH3
10
CH3
9
CH3 8

7
5 3 CH3 O 6
4 2 1
H3C
6 H3 C 3 5 CH3
1 2 4
O O
O O

3-ethyl-5-methylhexane-2,4-dione 5-(1-oxoethyl)decane-2,7-dione

O O O O O O
H C C H H C CH2 C H H C CH2 CH2 C H
ethanedial propanedial butanedial
(oxalaldehyde) (malonaldehyde) (succinaldehyde)

O O
HO OC CO OH
HOOC COOH
HO C C OH CH2 CH2 CH 2
ethanedioic acid propanedioic acid butanedioic acid
(oxalic acid) (malonic acid) (succinic acid)

HOOC(CH2)3COOH 1 5
COOH COOH
(pentanedioic acid/glutaric acid)
2 4
3
HOOC(CH2)4COOH
(hexanedioic acid/adipic acid) 2-ethyl-4-isopropylpentanedioic acid

H2N 1 O
4
O O 2
3 3
1 5
O 4 2 O
5
6
O NH2 2-ethyl-5-methylhexanediamide
diisopropyl 2-methylpentanedioate
(Please read di(propan-2-yl) for diisoprpyl)
H3C CH3

CH3

O O CH3

O O

1-ethyl 5-isopropyl 2-methylpentanedioate

2 4
Cl 6
1 3 5 Cl 4
NC 2 1
5 3
CN
O O
3-ethyl-2-methylpentanedioyl dichloride 2,4-dimethylhexanedinitrile

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Compound containing 3 or more identical carbon-bearing terminal functional groups :

Case-I If the 3rd group is directly bonded to the principal chain containing two groups, then all the three are
not included for the parent carbon chain. In such case, the following suffixes are used after alkane.

alkane tricarboxylic acid(acid); trialkyl alkanetricarboxylate(ester);

alkane tricarbaldehyde(aldehyde); alkanetricarbonitrile(nitrile);
alkane tricarboxamide(amide); tricarbonyl trichloride(acid chloride)

OCH2CH3
OH
O
O O O
O
2
4 2 3 1
3 1 CH3CH2O OCH2CH3
OH
4 5
HO O
butane-1,1,2-tricarboxylic acid triethyl pentane-1,2,3-tricarboxylate

O H CN CH 3
6 O Cl
H O
H 3C 3 5
2 2 4
Cl 1 Cl
O 3 1 H
1 CN
propane-1,2,3-tricarbaldehyde CN O O

methanetricarbonyl trichloride
2-methylhexane-1,3,4-tricarbonitrile

Case-II: If the 3rd group is not directly bonded to the carbon chain, then two groups in the chain are included
in the principal chain, the third becomes subbranch of an alkyl branch eg. carboxymethyl, amioncarcarbonylmethyl
etc.
1
3
HOOC 5 7
5
4
2
2 3 1
4 COOH
6 CN CN

CN
COOH
4-carboxymethylheptanedioic acid 3-cyanomethyl-2-methylpentanedinitrile

3'
2' COOCH2 CH3
1'
CHO 2'
1 1'
3 5
OHC 2 4
6 1 3 5 7
CH3CH2O OC 2 4 8
CHO 6
COOCH2 CH 3

2-methyl-3-(2-oxoethyl)hexanedial diethyl 3-methyl-5-(3-ethoxy-3-oxopropyl)octanedioate

SAQ: Give the IUPAC names of the following compounds from their line structures.

OH O
(i) (ii) (iii)
OH COOH

O
NH2 SO 3 H O

Cl H
(iv) (v) (vi) OH

Br OH CN

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

COOH
O O
CH3 H3C
CH3
Cl
(vii) H3C O (viii)
CH3
SO 3 H
CHO

HS OH
OH
S NH2
(ix) (x) H
(xi)
CH3
CH3
OH

H3C
CH3
H3C
(xii) S CH3 (xiii) OH

O
CH3
O

CH3

O
CH3
H3C
(xiv) (xv)
O OH
H3C CH3
CHO

Asnwer:
(i) pent-4-en-2-ol (ii) 2-methylhex-3-ynoic acid
(iii) 5-hydroxyhexan-3-one (iv)3-amino-2-bromo-5-chloroheptan-4-ol
(v) 2-methyl-5-oxopentanenitrile (vi)2-methyl-3-sulfobutanoic acid
(vii) 7-tert-butoxy-6-formyl-3,5-dimethyl- 7-oxohept-4-enoic acid
(viii) 6-chloro-4-methyl-6-oxohex-1-yne-3-sulfonic acid

(ix) 2-(prop-1-enyl)hexan-1-ol(new); 2-butylpent-3-en-1-ol(old)

(x) 3-aminopropane-1-thiol
(xi) 4-sulfanylbutan-2-ol (4-mercaptobutan-2-ol) (xii)7-(propan-2-ylthio)octan-4-ol
(xiii) 7-oxo-4-(prop-1-enyl)octanoic acid(new);4-(3-oxobutyl)hept-5-enoic acid(old);
(xiv)3-(but-1-enyl)-6-ethyl-7-methyloctan-2-one(new); 3-(3-ethyl-4-methylpentyl) hept-4-en-2-one(old) ;
(xv) 4-formyl-5-phenylhept-2-enoic acid
SAQ: Write the IUPAC names of the following compounds.

H3C CH3
HC
CH
CH2

(i)H3C (ii)H 3 C CH2

CH3 H 2C
H3C

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

H3C CH2

CH3 CH3

H2C

(iii)

CH

CH3
H3C CH3

CH3

H3C CH2

CH2
(iv) (v)
H3C
CH3 CH3

CH3

Answer:

(i) 4-ethynyl-2-methyl-5-(pent-2-en-2-yl)undec-2-en-8-yne
(ii) 3-ethynyl-4-methyl-5-methyidenehepta-1,6-diene
(iii) 3-ethynyl-4-(prop-1-en-2-yl)-6-methyldeca-1,3,6-trien-8-yne
(iv) 4-ethenyl-6-methyl-7-(propan-2-ylidene)undeca-2,5,9-triene
(v) 6-ethyl-4-methylidene-5-(prop-1-enyl)dodeca-7,9-dien-2-yne
SAQ: Write the IUPAC names of the following.

O
H2N NH2
HO
O
O O
(i) NH2 (ii) H
NH 2
O O

NH2 NH2 NH2 NH2

O O O O
(iii) (iv)
O O H2N O
H3C

H 2N
O CH3 OH
O O

O
O
(v) (vi) (vii)
O O
Cl
HO
HO OH OH
O

O O O

NH CH3
H3C CH3

(viii) (ix) H3C NH

CH3

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds
O

CHO Cl
O

H3C

(x) (xi) Cl

Cl
CHO CHO

O O CH3

(xii)H3C O O CH3

CH3

Answer:
(i) 3-(2-amino-2-oxoethyl)-2,3-dimethylpentanediamide
(ii) 3-(2-amino-2-oxoethyl)-6-oxohexanoic acid)
(iii) methyl 7-amino-2-(3-amino-3-oxopropyl)-7-oxoheptanoate
(iv) heptane-1,3,7-tricarboxamide
(v) 4-(aminocarbonyl)-7-oxoheptanoic acid
(vi) 9-chloro-5-formyl-6-(methoxycarbonyl)-9-oxononanoic acid
(vii) propane-1,2,3-triol(glycerol)
(viii) 2-methylnonane-3,5,7-trione
(ix) N,N’-dimethylbutane-1,4-diamine
(x) pentane-1,1,3-tricarbaldehyde
(xi) 3-(2-chloro-2-oxoethyl)hexanedioyl dichloride
(xii) 5-ethyl 1-(propan-2-yl) 2-methylpentanedioate
(When two alkoxy(OR’) parts of diester are different, each alkyl group is prefixed with the locant of carboxyl
carbon to which the alkoxy group is attached)

SAQ: Draw the structures of the following.

(i) ethyl 6-cyano-4-methyl-3-methylidenehepta-4,6-dienoate
(ii) methanetricarbaldehyde
(iii) 2,3,4,5,6-pentahydroxyhexanal
(iv) 3-ethenyl-2,3,6-trimethylocta-1,6-dien-4-yne
(v) 3-(2-amino-2-oxoethyl)pentanediamide
Answer:
CN CH3
OHC

6 4 2 O CH3
H2C 5 3 1 CHO
(i) 7 (ii)
CH2 O OHC

OH OH O CH2
H3C 7 CH2
8 1
H
6 5 4 3 2
(iii) (iv)
OH OH OH
H3C CH3 CH3

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds
Naming Bivalent and Multivalent Radicals:

Divalent radicals using the suffix ‘idene’ has been already discussed. That is case when one H atom is removed
from a monovalent alkyl group. Similarly when two H atoms are removed from a monovalent alkyl group, it
becomes a trivalent radical.
Trivalent radical: yl of alkyl is suffixed with ‘idyne’.

CH : methyl+idyne = methylidyne CH3 C : ethyl + idyne = ethylidyne

Note that these radicals cannot attach with any carbon chain. However such groups are used in complex
compounds of metals ions as ligands.
Bivalent radicals obtained by removing H atom from the two terminal carbon atoms(two monovalent radicals
in one species) of a normal alkane(unbranched)

The suffix ‘ene’ is used after polymethyl : polymethyl+ene = polymethylene

CH2
CH2 tetramethyl+ene = tetramethylene (butylene)

–CH2–CH2– : ethyl + ene = ethylene

Similarly hexamethylene, pentamethylene etc. These namings are used in trivial systems, eg.
(1) hexamethylene diamine(for hexane-1,6-diamine) (2) ethylene dichloride(1,2-dichloroethane)
Multivalent radicals on two terminals :
alkane + diyl + idene (if both the terminals are C=)
alkane + diyl + idyne (if both terminasl are C )
alkan+yl+ylidene (if one is C– and other is C=)
CH
CH butane+diyl+idene = butanediylidene

CH
CH butane + diyl + idyne = butanediylidyne

CH
CH butan-1-yl-4-ylidene

Such groups(restricted to divalent on either side) can be used in naming compounds in trivial system eg
butanediylidene diimine. However trivalent radicals on either side cannot be used often usually in organic
structures.

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Naming of Alicyclic compounds:

cyclopropane cycloprpyl cyclobutane cyclobutyl cyclopentane cyclopentyl

cyclohexane cyclohexyl

Naming aliphatic compounds with cyclic branches:

O OH
O

Cl
O

5-cyclopropyl-4-oxoheptanoyl chloride 1-cyclobutyl-3-hydroxybutan-1-one

* If the cyclic ring is attached to one carbon atom or one functional group, then the naming should be
done as a cyclic compound. In other words, if the higher priority functional group is directly attached to the
ring, then it is named as a cyclic compound.
* If the cyclic ring is attached to more than one carbon, then it can have two alternative names : (i) as an
aliphatic compound with cycloalkyl prefix or (ii) a cyclic compound with aliphatic prefix. The aliphatic name is
preferred(PIN)j in such case. See the following examples.

COOH CH2COOH

cyclobutane carboxylic acid 2-cyclopentylethanoic acid(aliphatic name)

(not cyclobutylmethanoic acid) carboxymethylcyclopentane (cyclic name)
4 2
3 1 2'
CO O H
3' OH
3'' 2'' 1'' 2
4' 1' 1
HO CH2 CH2 CH2 CH CH2 OH

3-cyclohexylbutanoic acid 1-[4-(3-hydroxypropyl)cyclohexyl]ethane-1,2-diol

Only in case of the 1st compound, the cyclic name is preferred. In all the other three examples, the aliphatic
names are preferred as the functional group is not directly bonded to the ring.
Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Other logic for naming as valid for aliphatic compounds are also valid for ring compounds. After the highest
priority group, C=C is considered(not other functional group) for LSL rule.

HO O
OH

1 H3C 1
6 2 6 2

5 3 5 3
4 4

cyclohex-2-en-1-ol 6-methylcyclohex-2-ene-1-carboxylic acid

O H O
CH3
1 CH3
6 2 1
2 6
5 3
4
3 5
4
OH

4-hydroxy-2-methylcyclohexanone 2-ethylcyclohexanecarbaldehyde

Cl O
H2N O

1 HO 1
6 2 6 2

5 3 5 3
O 4
4

5-oxocyclohex-2-ene-1-carboxamide 6-hydroxycyclohex-3-ene-1-carbonyl chloride

O O
H3C HO 2 NH2
1 3
HO 1
2 6
6 4
3 5 5
4 O

methyl 2-hydroxy-5-oxocyclohexanecarboxylate 3-aminocyclohexanol

NH2

1 O

OH

2-ethylcyclohexanol O NH2
(2-ethylcyclohexan-1-ol)
2-(8-amino-8-oxooctyl)cyclohexanecarboxamide

COOH
OH

cycloprop-2-ene-1-carboxylic acid 3-cyclobutylpropan-2-ol

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

NH2
CH3
CH3

H2N
CHO
3-methylcyclohexane-1-carbaldehyde
OH

1-(2,4-diaminocyclohexyl)propan-1-ol

NH2 OH
CONH2

2-aminocyclopentane-1-carboxamide cyclobut-2-en-1-ol

SAQ : Write the IUPAC names of the following.

H 2N O
O O
CH3 CH3

OH
OH
(i) (ii) (iii)
O

HO

H 3C

CH3

CH3
HO

(iv) (v)
CH3
OH

CH3
NH 2
HO CH3

H3C

CH 3
(vi) COOH
(vii) (viii)

CH3
CH3

Answer:
(i) 3-(6-methylcyclohex-1-enyl)propan-1-ol
(ii) 3-[2-(aminocarbonyl)cyclohexyl]propanoic acid
(iii) 4-(3-formylcyclopentyl)-2-methylbutanoic acid
(iv) 1-cyclopentylethanol
(v) 2-(2,3-dimethylbutyl)cyclobutanol
(vi) 3-(5-hydroxycyclohex-2-enyl)-2-methylpropanoic acid
(vii) 2-(2,2-dimethylbutyl)cyclopropanamine
(viii) 1-ethyl-2-propylcyclohexane

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

AROMATIC COMPOUNDS:

Benzene(C6H6): It is primarily the hybrid of the two resonating structures.(Refer Chemical Bond for details).
Benzene and its derivatives are aromatic compounds. Such compounds are unique in their behaviour. They
are more stable and hence less reactive than their acyclic analogue hexa-1,3,5-triene apart from having
acceptable fragrance(aroma). The details of aromaticity will be discussed later in the chapter aromatic
hydrocarbons.

(Resonance Hybrid)
Resonating Structures

All the six positions of benzene are equivalent.

(C6H5–) phenyl CH2 (benzyl)

Monosubstituted Benzene:
1 2
CH 3 Cl OH NO 2 NH2 COOH COCH3
CHO

toluene chlorobenzene phenol nitrobenzene aniline benzaldehyde benzoic acid acet ophenone
(methylbenzene) (hydroxybenzene) (aminobenzene) (1-phenylet hanon

CN COCl CONH2 COONa OCH3 O

COOCH3

methoxybenzene benzophenone
benzonitrile benzoyl chloride benzamide sodium benzoate methylbenzonate (anisole) (diphenylmethanone)

NO
CH2 Cl
(nitrosobenzene) chloromethylbenzene
biphenyl (benyl chloride)

Cl
Cl
C Cl
CH Cl
dichloromethylbenzene Cl
trichloromethylbenzen
(benzal chloride) (benzotrichloride)
If the functional group is not directly bonded to the benzene ring, then the compound is named as aliphatic.

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

OH

COOH
CH2 OH
OH
phenylmethano
phenylmethanol phenylacetic acid (benzyl alcohol
triphenylmethanol

SAQ III.8: Write the IUPAC names of the following compounds.

H3 C CH3
CH2 CH3 CH COCH2CH3 OCHCH3 COOCH(CH3)2
I

(i) (ii) (iii) (iv) (v) (vi) (vii)

Answer:
(i) ethylbenzene (ii) isopropylbenzene(cumene)
(iii) propiophenone(1-phenylpropan-1-one) (iv) ethoxybenzene
(v) isopropylbenzoate (vi) iodobenzene
(vii) 1,2,3-trimethylbutylbenzene

SAQ: Write the IUPAC names of the following.

CHO
CH3 H3C

NH2 O CN CH3
Cl
(i) (ii) (iii) (iv) (v) CH3
O

Answer: (i) (chloromethyl)benzene(Cl is not a functional group) (ii) 1-phenylmethanamine

(iii) methyl 2-phenylacetate(ethanoate) (iv) phenylacetonitrile(phenylethanenitrile)
(v) 2,3-dimethyl-3-phenylbutanal
Disubstituted Benzene :

X X X
1 1 1
6
2 Y 6 2
6 2

3 5 3
5 3 5
Y 4
4 4
Y
1,2- or ortho 1,3- or meta 1,4- or para

There are three isomers for two substituents namely (i) ortho(1,2) (ii) meta(1,3) (iii) para(1,4). There two
equivalent ortho positions with resepct to a particular substitutent on either side of it. Similarly there are two
equivalent meta positions for group. But there is only one para position.
Naming:
Rules: Priority order among Type C groups are the same as for aliphatic compounds.

-COOH >-SO3H > -COOR’ > COCl > CONH2 > -CN > -CHO > -COR > -OH > -NH2
(I) If the comounds has both or at least one Typce C group, then the parent compound is given after the
higher priority group, the other one appears as branches(prefixes) see these examples.
Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

2 NH2
COOH 1 CN 3
1 3
2
HO 2
4
1
OHC
HO
salicylic acid 4-formylbenzonitrile 3-aminophenol
(2-hydroxybenzoic (p-formylbenzonitrile) (m-aminophenol)
acid/ o-hydroxybenzoic (not 4-cyanobenzaldehyde) (not 3-hydroxyanilin
acid)

H3C CH3
N COCH3 COCH3
OH

SO3H
NO2

N,N-dimethyl-4-nitroaniline 3-acetylbenzenesulfonic acid 2-hydroxyacetophenone

(II) If both groups belong to type A (not type C), then the alphabetic senior group will get the lower locant.

NO2
4 CH3
2
Cl
1
1
CH3 CH3
1-ethenyl-3-methylbenzene(PIN 1-chloro-2-methylbenzene(PIN
1-methyl-4-nitrobenzen
(3-ethenyltoluene) (2-chlorotoluene)
Or, 4-nitrotoluene

OCH3
4

HO
1
1
2 2-(4-aminophenyl)phenol
CH2CH3 H2N
1-ethyl-4-methoxybenzene(PIN
(4-ethylanisole)

* If aromatic and aliphatic parts contain type C group, then the part bearing higher priority functional
group gives the parent name. If idential functional group present in both the parts, then it will be named as
aromatic.
CH3
COOH
CHO

H3C
HOOC
HO HO CH3

(4-hydroxyphenyl)acetaldehyde 4-(2,2-dimethylbutyl)phenol 4-(carboxymethyl)benzoic acid

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

1 OH
OH
2

NH2
phenylm ethanol
(3-aminophenyl)methanol

Identical groups:

OH OH OH
COOH
OH

COOH
OH
OH
pyrocatechol resorcinol hydroquinone phthalic acid
(1,2-dihydroxy (1,3-dihy droxy (quinol/1,4-dihy droxy (benzene-1,2-dicarboxy lic
benzene/o-dihydroxy benzene/o-dihy droxy benzene/p-dihy droxy acid)
benzene) benzene) benzene

CH 3
COO H COO H CH 3
CH 3

CH 3
COO H
COO H
o-xylene m-xylene
isophthalic acid terephthalic acid (1,3-dimethyl
(benzene-1,3- (1,2-dimethyl
(benzene-1,4- benzene/o-dimethyl benzene/m-dimethyl
dicarboxylic acid) dicarboxylic acid) benzene)
benzene)

NH2 NH2
CH3 NH 2
NH2

NH2
NH2
CH3
p-xylene benzene-1,2-diamine benzene-1,3-diamine benzene-1,4-diamine
(1,4-dimethyl (1,2-diam inobenzene/ (1,3-diam inobenzene/ (1,4-diam inobenzene/
benzene/p-dimethyl o-pheny lenediam ine) m -pheny lenediam ine
) p-pheny lenediam ine
)
benzene)

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

SAQ III.10: Write any one IUPAC name of the following aromatic compounds.

CH3 COOH CH2CH3

Cl NO2

NH2 O2N SO3H NO2

Cl
CN COCl
Cl Cl CH(CH3)2

O 2N NO2
NO2
CONH2
COCH3
C2H5 OC H2 CO OH
CHO CONH2 COOC2H5
Br Cl
H2NOC

CHO
I CN CH3 Cl

Answer:
3-methylaniline(m-toluidine), 1-chloro-2-nitrobenzene(o-nitrochlorobenzene), 3-sulfobenzoic acid, 1-chloro-4-
ethylbenzene, 1,2-dinitrobenzene, 1,3-dichlorobenzene, 1-isopropyl -2-nitrobenzene, 4-acetylbenzonitrile, 3-
(aminocarbonyl)benzoyl chloride, 1,3-dinitrobenzene, 1-bromo-3-iodobenzene, benzene-1,3-dicarbaldehyde,
benzene-1,2-dicarboxamide, ethyl 4-cyanobenzoate, 1-ethyl-4-methylbenzene, 2,4-dichlorophenoxyacetic acid
SAQ III.11: Write the preferred IUPAC names of the following compounds.

H 3C CH 3 CHO CN
NH2
N

CH3

CH 3
(i) (ii) (iii) CH3
CH3

CHO

CH 3
CHO CH 3

COOH COOH
(iv) (v)
NO 2

Answer:
(i) 3-[2-(dimethylamino)phenyl]butanal (ii)2-(2-methylprop-1-enyl)aniline
(iii) 3-(1-oxopropan-2-yl)benzonitrile (iv)2-(2-formylphenyl)propanoic acid
(v) 3-methyl-4-(2-nitrophenyl)but-2-enoic acid

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Tri or polysubstituted benzene:

1. If one of the groups belongs to type C, then the name is given after that groups getting locant 1. If more
than one of such groups are there, then the highest priority groups determines the name of the compound.
2. If all the groups belong to type A, then LSL rule determines the name. See these examples.

OH Br NO 2
2 1
5 Br 1 3 Br 6 2
6
4
5 3
1
3 COOH O2 N 4
NO2
2
1,2,3-tribromobenzene 1,3,5-trinitrobenzene
CH 3
5-hydroxy-2-methylbenzoic acid

CHO CONH 2
Br
6 NC 2
HO 1 2 OH
1 3
5 1 NH2 6

2 6 4 5 3
4
Br Br 5 COCH3 4
3
2,4,6-tribromoaniline 4-acetyl-2-formylbenzonitrile 2,6-dihydroxybenzamide

3
CH3 2 4 Cl H2N 1 5 Cl
1 2
4
O2N O2N 3
4-chloro-2-methyl-1-nitrobenzene(correct) 5-chloro-2-nitroaniline(correct)
5-chloro-2-nitrotoluene(wrong) 2-amino-4-chloro-1-nitrobenzene(wrong)

CH3
2
CH2CH3 O 2N 3 NO2
4
1
3
4 6
2-chloro-4-ethy l-1-methoxy benzene
2 5
Cl (not 3-chloro-1-ethy l-4-m ethoxy benzen NO2
1

OC H3 2-methyl-1,3,5-trinitrobenzene(PIN
(2,4,6-trinitrotoluene)

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

SAQ:

COOCH3 COCH3 COOCH3

CH3 C 2H5
CH3

COOCH3
O 2N
NO 2 O 2N CHO

OC 2H5 NO 2 COCl
Br I O2N NO 2
H 3C NH2

H 3C NO 2 COOH
Cl
Cl Cl
CH3

Answer:
methyl 2-methyl-5-nitrobenzoate, 3-acetyl-5-nitrobenzaldehyde, 4-ethyl-2-methyl-1-nitrobenzene, dimethyl
phthalate, 1-bromo-3-chloro-5-iodobenzene, 2-chloro-4-ethoxy-1-methylbenzene, 3,4-dimethyl-2-nitroaniline, 1,2,4-
trinitrobenzene, 2-chloro-5-chlorocarbonylbenzoic acid

DIAZINES/AZO and AZOXY Compounds:

HN=NH : diazene CH3 N N CH3 (dimethyldiazene)

1
N N 2
1
N N
2

diphenyldiazene (1-naphthyl)(2-naphthyl)diazene
(azobenzene) (1,2’-azonaphthalene)

1 Cl 3
2 2 2 3
N N
1 1 4
N N Cl

(2-naphthyl)phenyldiazene (3-chlorophenyl)(4-chlorophenyl)diazene
(naphthalene-2-azobenzene) (3,4'-dichloroazobenzene)

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

2
NH2 CH3
1 2
1 3
N N
4 N N 4 1 SO H
3
Cl

1-[(4-chloro-2-methylphenyl)diazenyl]naphthalen-2-amine 4-(phenyldiazenyl)benzenesulfonic acid

1
O SO3H
3
N N
N3

diphenyldiazene oxide 3-azidonaphthalene-2-sulfonic acid

(azoxybenzene) (N3– = azido group)
Diazoninum compounds: Compound containing R-N2+ X– are called alkanediazonium halide (not alkyldiazonium
halide)

CH2 CH2
H3C N N Cl H3C N N Cl (covalent structure)

ethyanediazonium chloride

-
N N Cl N N Cl (covalent structure)

benzenediazonium chloride

1 + -
HO 7 N2 BF4
N N OH

7-hydroxynaphthalene-2-diazonium tetrafluoroborate phenydiazenol (benzenediazonium hydroxide)

CH2NH2: (diazomethane)

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

POLYNUCLEAR AROMATIC COMPOUNDS

Compounds containing more than one benzene ring fused at the ortho or 1,2 positons are called polynuclear
or condensed aromatic compounds. A few examples are given below.

8 1 5 4

7 2 6 3

or
3 7 2
6
5 4 8 1

(napthalene)
9 5 10 4
8 1
7 2 6 3

or 2
6 3 7

4 8 9 1
5 10
(anthracene)

Then tetracenene(four benzene rings fused linearly), pentacene and so on.

Monosubstituted naphthalene:
For monosubstituted naphthalene, there are two non-equivalent positions namely 1-(α) or 2-(β).

1 1
2 2

2 2
1 1
Di- or polysubstituted naphthalene:
For such compounds the numbering of carbon atoms is shown before. The highest priority functional group
to get the lower locant.

CHO
OH

COOH H3C

naphthalen-2-ol naphthalene-1-carboxylic acid 6-methylnaphthalene-1-carbaldehyde

(β-naphthol)

4 5 5 4
CH3 OH H5C2 6
6
1
CN
2
1 1
COOH NH2

1-methylnaphthalene-2-carbonnitrile 6-hydroxynaphthalene-1-carboxylic acid 6-ethylnaphthalen-1-amine

Anthracene:
For monosubstitued anthracene has 3 non-equivalent position, 1, 2 and 9. But for di- and polysubstituted
anthracene, the numbering has been given before.

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

1 9 1 OH
2 2 COOH

2 2
1 9 1
anthrancene-2-carboxylic acid anthracen-9-ol

1 OH
2 CHO 9
1
2 NO
7 2

5 6
4
5 4
CH3 CH3

5-methylanthracene-2-carbaldehyde 4-methyl-2-nitroanthracen-9-ol
Heteroaromatics and Heterocyclics:
4 4
4 3 4
3 3
5 3

5
5 2 5
2 2
6 2
N
O H S N
1 1
1 1

furan pyrrole thiophene pyridine

4
4
5 3
5 3

6 2
2
6 1
N
O O
H O
1

4
4 3 4 3 4 3
5 3
5 1 2 5 1 2 5 1 2 1
NH O S 6 2
N
pyrrole funran thiophene pyridine
N COOH

NH CHO O
N
pyrazine pyrrole-2-carbaldehyde furan-3-carboxylic acid

OH
CH3

N
3-methylpyridin-4-ol

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds
Other Heterocyclic Compounds:
O

NH O O O
piperidine tetrahydrofuran(THF) oxane 1,3-dioxane

NH NH
NH HN NH

NH NH NH NH O
piperazine 1,4-dihydropyrazine 1,3-diazinane 1,3,5-triazinane 4-H-pyran
(1,4-diazinane)

Bicyclic Compounds:
A bicyclic compound is one which can be converted to an open chain acyclic compound by making
cleavage(scission or breakage) of covalent bonds two times.

1st cleavage 2nd cleavage

open chain

bridgehead carbon

bridges

bridgehead carbon
There are two bridge head carbon atoms and three bridges. The bridge may contain only a single covalent
bond(no carbon atom).
bicylo[x.y.z]alkane
x, y and z are ring size i.e number of carbon atoms in three bridges from highest to lowest bridges. This
excludes the two bridgehead carbon atoms. If a bridge has no carbon atom(only a covalent bond) then it will
get the numeral ‘0’.
alkane will be from (x+y+z) +2 i.e all the carbon atoms. The numbering will start from one bridgehead
through the longest bridge to the other bridgehead, then to bridge of intermediate length and shortest bridge.
For naming a branched bicyclic compound, the priority order of functional group and LSL to be taken into
account.
10

9
2

3 1

8 bicyclo[4.3.1]decane
4
6
7
5

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

2 1 3 1 0 1
2 5
0

bicyclo[2.2.0]hexane bicyclo[5.3.1]undecane bicyclo[1.1.0]butane

H3C 2 1 10
H3C
3
11
5 4 3
4 9
7

5 6 8
6 1 2

5-methylbicyclo[2.2.0]hex-2-ene 3-methylbicyclo[5.3.1]undec-8-ene

CH 3 OC H 3

6 4 5
5 7
8 3
10 6
HO
4 9 9
2 7
O 2N
1
3 1 8
2
6-m ethylb icyclo[5 .2.1]dec-3 -ene 4- m ethoxy-2-nitrobicyclo[3.2.2]nonan-6-ol
SAQ:
SAQ III.14:Write the names of the following bicyclics.
CH3

H3C

(i) (ii) (iii) CH3 (iv) (v) (vi)

H 2N
OHC

COOH
(vii) (viii) (ix) (x)
H2 N
H 2N

Answer:
(i) bicyclo[1.1.1]pentane (ii)bicyclo[2.2.2]oct-2-ene (iii)7-methylbicyclo[4.2.1]non-3-ene (iv)9-
ethylbicyclo[3.3.2]decane (v)bicyclo[4.4.2]dodec-11-ene (vi) 8-methylbicyclo[5.2.0]non-2-ene
(vii)bicyclo[5.3.1]undec-4-en-2-amine (viii)5-aminobicyclo[4.2.1]non-2-ene-7-carboxylic acid (ix)bicyclo[3.2.2]non-
2-en-6-amine (x)bicyclo[3.1.1]hept-2-ene-6-carbaldehyde

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

SPIRO COMPOUNDS:
The compounds in which two rings share one common carbon atom are called spirocompounds.
spiro[x.y]alkane
x and y are chain lengths in the two rings or the number of carbon atoms in the two rings which link to the
common atom(called spiro atom), which are separted by full stop. Note that the spiro atom is excluded in
these numbers. The numbers are written in increasing order eg. [4.5] unlike that followed in bicyclic
compounds(decreasing order). While naming the parent alkane the total number of carbon atoms in the
compound is counted.

1 6 7

5 8

4
10 9

spiro[4.5]decane

The numbering starts in the smaller size ring from the carbon atom adjacent to the spiro atom and
proceeds around the smaller ring back to spiro atom and then proceeds around the second ring(larger
size ring). While going from the smaller ring towards the larger ring the lowest set of locants rule is
kept in mind. If there is a C=C, then ene should get the lower locant compared to alkyl or other type
A groups.

6 4
6
5
3 7 3
7
4 5
4 2
5
1
8
1
3 6 10
9 8 2
2 9 1
8 7
H 3C
spiro[4.4]nona-2,7-diene
1 -e th y ls p iro [3 .6 ]d e c -6 -e n e
H 3C

8-methylspiro[2.5]oct-4-ene

SAQ III.15: Name the following spiro compounds.

H3C

CH3
(i) (ii)- (iii)
H3C
H3C

CH3

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

(iv) Cl (v)
H 3C

Answer:
(i) 1,4-dimethylspiro[2.7]deca-5,8-diene (ii) 6-isopropylspiro[3.5]non-1-ene
(iii) 4-methylspiro[2.2]pent-1-ene (iv)1-chloro-5-ethylspiro[3.3]heptane
(v) 4-methylspiro[4.8]trideca-1,7,9-triene

SUBSTITUTED OXIRANES(EPOXYALKANES), IMINES, LACTONES, LACTAMS, IMIDES,

KETENES

1. Substituted oxirane: The O atom of oxirane is always numbered 1. Alphabetical seniority of alkyl groups
decides the correct direction of numbering. These are also named as epoxyalkanes, the locants of the epoxy
are to be prefixed to it.
1
O
3 2
H 3C CH CH CH 2 CH 3
2 -e th y l-3 -m eth y lo x ira n e
(2 ,3 -ep o x y p en ta n e)
2. Imines: =NH is called imine group. It is a bivalent group. The name of imine is alkan-x-imine where x is the
locant of imine.
H 3C CH 3
H 3C CH 2 CH 2 CH NH
b u ta n -1 -im in e NH
p ro p a n -2 -im in e
3. Lactones: Cyclic esters are called lactones. Butyrolactone, valerolactone, caprolactone are a few examples
of lactones.
CH 2 CH
H2 CH 2 2
C H 2C CH 2 H 2C
H 2C CH
O 2
H 2C H 2C O H 2C
C C O
C
O O
O
-b u tyrolacto n e -vale rolacto n e -capro lacton e
4. Lactams: Cyclic amides are called lactams. Butyrolactam, valerolactam, caprolactam are few examples of
lactams.
CH 2 CH 2
H2 CH 2
C H 2C CH 2 H 2C
H 2C CH 2
NH
H 2C H 2C NH H 2C
C C NH
C
O O
O
-butyro lactam -valero lactam -capro lactam

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

5. Ketenes: R-CH=C=O are called ketenes. Such compounds are named according to IUPAC rule.
Example: CH3-CH=C=O prop-1-en-1-one
6. Imides: Imides contain -CO-NH-CO- group. It is analogous to acid anhydride except -O-in anhydride
is replaced by -NH- in imide. They are named according to IUPAC rules.
CH 3-CO-NH-CO-CH3 N-acetylacetamide.
ALTERNATIVE NAMING PROCEDURE FOR ETHERS AND 20 AMINES
Ethers:(OXA System)
1. Oxygen atom in ether is treated like a carbon atom in finding out the longest continuous chain
including the oxygen atom. In otherwords, the oxygen atom is counted like a carbon atom in determining
the the name of parent alkane. The ether group(oxygen atom) is indicated by the prefix oxa with
its locant placed before it. Lowest set of locants rule is followed while choosing the direction of
numbering. Note that ether group (O atom) does not enjoy any priority as functional group.

5 3 CH3
1

H3C O 2
6 4

(2-methyl-4-oxahexane)
CH3

Note that IUPAC does not have a fixed procedure for naming ethers, although the one discussed
before(alkoxyalkane) is the preferred name. The oxaalkane procedure of naming ether is simpler,
although used to a lesser degree of preference.

Cyclic ethers:
When oxygen atom remains as a part of a ring, it is a cyclic ether. The systematic names of these ethers
and their alternative names according to oxa system are given below.

O O O O

O
oxirane oxetane oxacyclopentane 1,4-dioxacyclohexane
(oxacyclopropane) (oxacyclobutane) (tetrahydrofuran or THF) (1,4-dioxane)

Note that oxirane is also commonly called ethylene oxide or epoxyethane.

Sec-amines (AZA System)
Like oxygen atom in ether, the nitrogen atom in a sec-amino group( NH) is counted like a carbon atom
in finding out the longest continuous chain. The prefix aza is used for the amino function with its locant before
it.
4 2 OH

H3C NH 1
5 3
3-azapentanoic acid [ 2-(ethylamino)acetic acid/N-ethylglycine]
O

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

Trivial System(Common Names):

Type of Carbon atoms:
(a) Primary (10) (b) secondary (20) (c) tertiary(30) (d) quaternary(40)

CH3
CH3
10 20
30 40
CH3 CH CH2 C CH3
CH3

Types of Alkyl Groups:

(a) n-alkyl : straight chain : example n-propyl, n-butyl, n-pentyl etc. ( n = normal)

CH3 CH2 CH2 CH3 CH2 CH2 CH2

n-propyl n-butyl
(b) sec-alkyl: derived from a 20 carbon atom. The carbon bearing the unsatistfied valency has one H atom.

CH3 CH2 CH CH3 CH3 CH2 CH CH2 CH3

sec-butyl sec-pentyl

CH3 CH2 CH2 CH CH3

sec-pentyl
There is only one sec-butyl and hence can be used in naming. But there are two sec-pentyl groups, hence cannot
be used for naming. Can you say how many sec-hexyl group you can have from hexane ? Again two. You will
get clear picture about this in the chapter ‘Isomerism’.
(c) tert-alkyl: derived from a 30 carbon atom. The carbon bearing the unsatisfied valency has NO H atom in it.

CH3 CH3

CH3 C CH3 C
CH3 CH2CH3

tert-butyl tert-pentyl
Since there is one from each of the above, they can be used in naming.

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

(d) isoalkyl group: contain -CH3 branch at the 2nd position.

CH3 CH3 CH3

CH3 CH CH3 CH CH2 CH3 CH CH2 CH2

isopropyl(sec-propyl) isobutyl isopentyl

Note that isopropy is also sec-propyl as it satisfies both the definitions. But isopropyl is preferred.
(d) neopentyl group:

CH3

CH3 C CH2
(neopentyl)
CH3

Naming by Common System(traditional or trivial system):

CH3 CH2 CH2 CH3 CH3 CH2 CH2 CH2 CH3

n-butane n-pentane

CH3
CH3 CH3
CH3 C CH3
CH3 CH CH3 CH3 CH CH2 CH3
CH3

isobutane isopentane neopentane

CH3
O CH3
CH3
CH3 C CH2 OH CH3 C CH
CH3 CH2 CH Cl CH3
CH3

sec-butyl chloride neopentyl alcohol isopropyl methyl ketone

CH3

CH3 CH2 O C CH3

tert-butyl ethyl ether
CH3

Dr. S.S.Tripathy
 Nomenclature of Organic Compounds

BRACKET SYSTEM OF STRUCTURE WRITING:

CH3 OH CH3
CH CH C COOH
(CH3)2CHCH(OH)C(CH3)2COOH =
CH3
CH3

CH3 O CH3

(CH3)3CCOCH(CH3)(CH2)3CH3 =
CH3 C C CH CH2 CH2 CH2 CH3
CH3

Short Notations:
n-Bu (n-butyl); i-Pr (isopropyl); t-Bu (tert-butyl); n-Pr ( n-propyl); Me(methl): Et(ethyl)

Dr. S.S.Tripathy