Organic Compounds

(a) Hydrocarbon - Organic compounds containing carbons and

hydrogens only.
Ex. - C3H6, C4H8, C2H6

(b) Hydrocarbon Derivatives - Organic compound which are

derived from hydrocarbons.
Ex. CH3Cl, CH3OH, CH3CHO, CH3CN

(c) Organometallic Compounds -Organic compounds in which

carbon-metal bond is present.
Ex. CH3MgBr, (CH3)2CuLi, (CH3)2Zn
 Representation of Organic Compounds

(i) Molecular Formula

(ii) Structural Formula

(iii) Condensed Formula

(iv) Bond line Representation

(i) Molecular Formula

It represents total number and type of different atoms present in the

compound.

Example C2H6 , C2H6O , C4H9N

(ii) Structural Formula

It represents atoms along with bond present between atoms.

H H H H
Example C2H6  H—C—C—H C2H5OH  H—C—C—O—H
H H H H
(iii) Condensed Formula

In this type of representation complete molecule is written in single

line without showing any bond.
Groups attached to carbon atoms are written in bracket in single line.

Example

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

H3CCH(CH3)CH3 CH3CH2C(CH3)2CH2CH3
(CH3CH2)2C(CH3)2
 (iv) Bond line Representation

✓ Frequently used representation of organic compound.

✓ In this type of representation bonds are written in zig-zag way and carbon
and their hydrogens are not shown.

✓ In this representation C–H bonds are not shown.

Atoms other than carbon and hydrogen are shown in formula.

✓ Corners and sharp edges represent carbon atoms.

Example
H3C—CH3 H3C—CH2—CH3
Example

Draw bond line representation of following compounds.

CH3—CH2—CH2—CH2—CH3

CH3
CH3—CH2—C—CH2—CH3

CH3

H3C—CC—CH3

OH Cl

H3C—C=C—CH3
Cl OH
 Example

Draw other representations of given compound H3C.CH(Cl).CH(OH).CH3

Solution
H H
H | | H
Structural formula H—C—C—C—C—H
H | | H
Cl OH

Cl
Bond-line notation

OH

Molecular formula C4H9ClO

 CLASSIFICATION
OF
ORGANIC COMPOUND
 On the Basis of Structure

Open-chain, acyclic Closed-chain, cyclic

Or aliphatic compounds compounds

Homocyclic Heterocyclic
Saturated Unsaturated
Compound Compound

Alkene Alkyne Alicyclic Aromatic Alicyclic Aromatic

Alkane
Cn H𝟐n Cn H(𝟐n−𝟐) Compound Compound Compound Compound
Cn H(2n+2)
 Aliphatic or open chain compounds

Those compounds in which first & last carbon atoms are not connected
with each other. Branched or unbranched chains are possible in these
compounds.

Example
CH3
CH3–CH2–CH2–CH3 CH3—CH2—CH—CH3 CH3—C—CH3
CH3 CH3
(Unbranched) (Branched) (Branched)
There are two varieties in these compounds

1. Saturated Hydrocarbons

Hydrocarbons in which carbon atoms are connected to each other by single

bonds.

Example CH3-CH2-CH2-CH3 CH3-CH2-CH2-CH2-CH3

2. Unsaturated Hydrocarbons

Hydrocarbons in which carbon atoms are connected to each other by double

or triple bonds.

Example CH3-CH=CH-CH3 CH3-CH=CH-C≡CH

 Closed-Chain (Cyclic) compounds

(a) Homocyclic

Cyclic compounds in which ring is made up of only one type of atoms.

(i) Alicyclic : Cyclic compounds which have properties of aliphatic compounds

are known as alicyclic compounds. These may be saturated or unsaturated
like aliphatic compounds.

Example
(ii) Aromatic(Homocyclic)

✓ Aromatic homocyclic compounds are cyclic compounds containing sigma

bonds, and delocalized  electrons between carbon atoms in a ring.

✓ They are known as aromatic due to their pleasant smell.

✓ They are highly stable in nature.

Example

OH NH2

Benzene
Phenol Aniline
 (b) Hetero cyclic compounds

✓ Cyclic compounds in which complete ring is formed by carbon and other

atoms like oxygen, nitrogen, phosphorous and Sulphur etc. These other
atoms are called hetero atoms.

(i) Alicyclic :

Example

O N
|
Tetrahydrofuran
Oxirane/Epoxide (THF) H
Piperidine
(ii) Aromatic(Hetreocyclic)

✓ Aromatic heterocyclic compounds are cyclic compounds containing

sigma bonds, and delocalized p electrons in a ring.

✓ In aromatic heterocyclic compounds two or more than two types of

atoms in a ring will be present.

Example

N
O S |
N
H
Furan Thiophene Pyridine Pyrrole
 Example

Classify the following compounds as Homocyclic, Heterocyclic, Aliphatic

saturated or Aliphatic unsaturated.
OH

O
Aliphatic Aliphatic Homocyclic Homocyclic Heterocyclic
unsaturated saturated

S N
H
Heterocyclic Aliphatic Heterocyclic Homocyclic
unsaturated
 Functional groups
Those atoms or group of atoms which are responsible for chemical property
of a molecule.

Functional groups Name Example

(1) — OH Alcohol
OH

(2) — SH Thioalcohol
SH

(3) — O — ether O

(4) — X(F, Cl, Br, I) Halogen

Cl
Functional groups Name Example

(5) — NH2 Amine

NH2

O
(6) Aldehyde C O

‖
—C—H H

O
(7) Ketone
—C— O

O
O
(8) Carboxylic acid
—C—OH OH
 Functional groups Name Example
O O
(9) ||
—C—X = Acid Halide
(—X=F, Cl, Br, I) Cl

O O
(10) || = Amide
—C—NH2 NH2

O O
(11) || = Ester
—C—O— O

—C—O—C— O O
(12) || || = Acid anhydride
O O O
 Functional groups Name Example

(13) —C≡N(CN) = cyanide CH3–C≡N

(14) —N = C(NC) = Isocyanide CH3–NC

O
||
(15) —SO3H = Sulphonic acid CH3–S—OH
||
O
CH3– N O

||
(16) —NO2 = Nitro
O
 Functional groups Name Example

ሷ
(17) —N=O = Nitroso N O

||
(18) —N=N — = Azo N N

||
(19) C=N—OH = Oxime N—OH

(20) C=NH = Imine H3C–CH=NH

 Functional groups Name Example

(21) = Cyclic ether

O O
OH

(22) = Phenol

(23) C=C = alkene They are also considered as

functional group, but they are

(24) —C ≡ C = alkyne not true functional group.

 Degree of Carbon & Hydrogan

How many carbon

directly attached to Type of carbon Type of Hydrogen Example
other carbon atom.

1C Primary/1° Primary/1° CH3—CH3

1° 1°

2C Secondary/2° Secondary/2° CH3—CH2—CH3

1° 2° 1°

1° 3° 1°
CH3—CH—CH3
3C Tertiary/3° Tertiary/3°
1° CH3

1°
CH3
1° 1°
4C Quaternary/4° Not possible CH3—C—CH3
4°

1°
CH3
 Example

Find degree of each carbon and hydrogen atoms in following :-

Structure 1°C 2°C 3°C 4°C 1°H 2°H 3°H

CH3–CH2–CH–CH–CH2–CH3
4 3 2 0 12 6 2
CH3 CH2CH3

CH2 = CH – CH – CH = CH2
CH 3 3 1 0 6 3 1
CH2

CH3
CH3– C – CH3 4 0 0 1 12 0 0
CH3
 Example

Find degree of each carbon atoms in following :-

NH—CH2—CH—CH3
CH3

Solution

Degree of Carbon Total No.

Degree of Hydrogen Total No.
Primary Carbon (1°C) 3
Primary hydrogen (1°H) 8
Secondary Carbon (2°C) 5
Secondary hydrogen (2°H) 5

Tertiary Carbon (3°C) 2 Tertiary hydrogen (3°H) 1

Quaternary Carbon (4°C) 0

DEGREE of Alcohol :—OH
Degree of Alcohol define by degree of carbon in which the −OH
group(Hydroxyl group) is bonded to Carbon atom atom.

Compounds Degree of Alcohol

H3C —CH2 —OH 1° alcohol

CH3
H3C — C — OH 2° alcohol
H

CH3
H3C — C — CH3 3° alcohol
OH
 Note

1°, 2° and 3° alcohols are considered as same functional group.

Phenol and Alcohol are not considered same functional group

OH

2° alcohol

Note

Degree of alkyl hailde is same as degree of alcohol.

 Degree of amine :—NH2

(1) Primary amine (1°) Secondary amine (2°) Tertiary amine (3°)
Nitrogen is bonded to Nitrogen is bonded to Nitrogen is bonded to
only one carbon atom. two carbon atom. three carbon atom.

H3C —CH2 —NH2

H2C =CH—NH2
NH2 N
N
H
CH3 CH3
H3C NH H3C — N — CH3

Note 1°, 2° and 3° amines are considered as different functional group.

Degree of amide:—CONH2

Primary amide Secondary amide Tertiary amide

Nitrogen is bonded Nitrogen is bonded to Nitrogen is bonded to

to only one carbon
atom. two carbon atom. three carbon atom.

O O O
H3C—CH2—C—NH2 H3C—CH2—C—NH —CH3 H3C—CH2—C—N—CH3
CH3

Note

1°, 2° and 3° amides are considered as different functional group.

 Example

Encircle the functional group present in molecule and write their name also
count total number of different functional group.

(i) O SH Cl
(ii)
O N
H H2N OH

NH2 O NC O H
 Example
OH

NH2 N O

HO
O

O NH2
O
O

Solution
 Homologous series

The Series of compounds in which all the members can be represented

by a general formula is known as homologous series and members of the
series are known as homologues.
 Characteristics of homologous series

(a) Two successive members (Consecutive) of same family are differ by

−CH2− unit or 14 molecular mass.

(b) If functional group is present then all the members must have same
functional group.

(c) All the members of series have same general formula.

(d) Homologues have nearly same chemical properties but there is a

regular change in physical properties.

(e) Members of homologues series have same general method of preparation.

Example

Alkane family General formula: CnH2n+2

+CH2 +CH2 +CH2

CH4 C2H6 C3H8 C4H10

Alkene family General formula: CnH2n

+CH2 +CH2 +CH2

C2H4 C3H6 C4H8 C5H10

Example

Alcohol family Gen. formula CnH2n+1OH/CnH2n+2O

+CH2 +CH2

CH3OH C2H5OH C3H7OH

Ether family Gen. formula CnH2n+2O

+CH2 +CH2

CH3OCH3 CH3OCH2CH3 CH3CH2OCH2CH3

Note 1°, 2° and 3° Amines/amides are considered as different

functional group so they form diffrent homologous series.
 Example

Which of the followings are homologous of each other?

OH OH COOH COOH
(i) (ii)

No Yes

O O

(iii) (iv) H
OH
O O
OH

No No
 Degree of unsaturation

It is the deficiency of H2 molecule (2H) in a compound with respect to

corresponding saturated hydrocarbon (Alkane).

Example

–2H
C3H8 : H3C – CH – CH2 H3C – CH = CH2
H H

–2H

C3H6
 Calculation of DOU

Case 1 : If 2D structure is given :-

DOU = number of  bonds + number of rings

Example

(1) (2)

DOU= 2 in both case

Example DOU

(3) 4

(4) 7

(5) 8
 Example

Find degree of unsaturation in following compounds.

COOH CN

(i) (ii)
O

Solution

Ans. (i) 5, (ii) 6

Case 2 : If molecular formula is given :-

H+X−N
C
DOU = (C + 1) –
2

= Number of carbon atom

= Number of hydrogen atom

= Number of halogen atom

= Number of nitrogen atom

 Example

C4H8
8+0+0
D.O.U. = (4 + 1) – =1
2
In C4H8 compound there may be one double bond present or one cyclic ring
present.
So, following structures are possible for C4H8.
 Example

Find degree of unsaturation of following compound.

H+X−N
DOU = (C + 1) –
2
(1) C3H2Cl2 2

(2) C5H11N 1

(3) C5H4ClBr 3

(4) C6H6O 4

(5) C6H3ClBrI 4
Case 3 : If 3-D structure is given :-

Molecular formula for cube = C8H8

 Example

Calculate DU of following compounds.

H+X−N
DU = (C + 1) –
2
1. C3H4 2

2. C2H5NO 1

3. C2H5Cl 0

4. C6H4O2Cl2Br2 3

Solution

Ans.
 HYBRIDISATION

Structure 𝝈&𝝅 Hybridization Bond angle Shape

C 4,0 sp3 109°28’ Tetrahedral

3,1 sp2 120° Trigonal planar

C

C 2,2 sp 180° Linear

C 2,2 sp 180° Linear

 Example

What is the hybridization of Carbon in the given compounds ?

1. H3C — C  N 2. H2C = C — CH2 — C  CH
CH3
3. H2C = C = CH2 4. H3C—CH2—C  C

Solution

sp3 sp sp2 sp sp2

1. H3C—C  N 3. H2C = C = CH2

sp2 sp2 sp3 sp sp sp3 sp3 sp sp

2. H2C = C — CH2 — C  CH 4. H3C—CH2—C  C

CH3 Lone pair is present in sp

sp3 hybridized orbital
 Example

sp sp sp2 sp2 sp3 Total  bonds = 10

HC  C — CH == CH — CH3 Total  bonds = 3

Example

H

C
H—C
 C—H
 Total  bonds = 12
120° Total  bonds = 3
H—C
 C—H

C

H
Flat hexagonal structure due to sp2 hybridised C-atom in benzene
 Example
1 2 3 4
In CH2=C=CH–CH3 molecule, the hybridization of carbon 1, 2, 3 and 4
respectively are : [JEE Main 2021]
(1) sp3 , sp, sp3 , sp3 (3) sp2 , sp, sp2 , sp3
(2) sp2 , sp2, sp2 , sp3 (4) sp2 , sp3 , sp2 , sp3

Solution

Ans. (3)
 IUPAC Nomenclature

Format for IUPAC Naming

Secondary + Primary + Word Root + Primary + Secondary

Prefix (2°P) Prefix (1°P) Suffix (1°S) Suffix (2°S)
Word Root

It represents number of carbon atoms in main chain.

No. of Carbon Root Word

1 Meth
2 Eth
3 Prop
4 But
5 Pent
6 Hex
7 Hept
No. of Carbon Root Word No. of Carbon Root Word
1 Meth 8 Oct
2 Eth 9 Non
3 Prop 10 Dec
4 But 11 Undec
5 Pent 12 Dodec
6 Hex 13 Tridec
7 Hept 14 Tetradec
15 Pentadec
16 Icos
Primary Prefix (1° prefix)

It represent nature of parent carbon chain

Nature of parent carbon chain 1° Prefix

Aliphatic —

Cyclic Cyclo

Bicyclic Bicyclo

Spiro Spiro
 Secondary Prefix (2° prefix)

✓ Groups which are part of molecule but does not become part of parent
carbon chain during IUPAC naming.

✓ Following groups are always treated as substituents in IUPAC nomenclature.

Substituents Sec. Prefix Substituents Sec. Prefix

–R Alkyl
–NO2 Nitro
–CH3 Methyl
–C2H5 –OR Alkoxy
Ethyl
–X –OCH3 Methoxy
Halo
–F –OC2H5 Ethoxy
Fluoro
–Cl —CH—CH—
Chloro Epoxy
–Br Bromo O
–I lodo –N=O Nitroso
Primary Suffix (1° suffix)

It denotes whether the compound is saturated or unsaturated.

C – C → ane C=C–C=C → diene

C = C → ene CC–CC → diyne

C  C → yne
 = enyne
C=C–CC → eneyne

✓ If a, e, i, o, u or y is present after ane, ene or yne then ‘e’ of ane/ene/yne

are removed.
SECONDARY Suffix (2° suffix)

✓ Give us information about main functional group.

 IUPAC Naming
of
Saturated Hydrocarbons
 IUPAC Naming of Saturated Hydrocarbons

Rule - 1

Select the longest continuous parent carbon chain.

Example

1. CH3 – CH2 – CH2 – CH3 2. CH3 – CH – CH – CH3

CH3 CH3

3. CH3 – CH2 – CH– CH3 4. CH3 – CH2 – CH– CH2 – CH3

CH2 – CH3 CH2
CH2
CH3
 IUPAC Naming of Saturated Hydrocarbons

Rule - 2
If more than one symmetrical carbon chain is present, then select the
one which has the maximum number of substituents.

Example

1. CH3 – CH2 – CH – CH2 – CH – CH2 – CH3

CH3 – CH CH2
CH3 CH3

2.
 IUPAC Naming of Saturated Hydrocarbons

Rule - 3
Numbering always starts from the terminal C-atom.
Numbering should be done according to the lowest set of locant rules
(LSLR).

1. CH3 – CH – CH2 – CH3

CH3

2. CH3 – CH – CH – CH2 – CH3

CH3 CH3
 IUPAC Naming of Saturated Hydrocarbons

Rule - 4
When two or more substituents are present at a symmetrical position,
then follow alphabetical order for numbering.

Example

CH3 – CH2 – CH – CH – CH2 – CH3

CH3 CH2– CH3
 IUPAC Naming of Saturated Hydrocarbons

Rule - 5
If two or more than two substituents are present, then they are written
in alphabetical order, along with their location.

Example

CH3 – CH – CH – CH3
Cl Br

CH3 – CH2 – CH – CH – CH3

Cl Br
 IUPAC Naming of Saturated Hydrocarbons

Rule - 6
If two or more than two substituents are the same, then use:
di for 2, tri for 3, tetra for 4, etc.

Example

CH3 – CH – CH – CH2 – CH3

CH3 CH3

CH3 – CH – CH2 – CH – CH3

Cl Cl
 IUPAC Naming of Saturated Hydrocarbons

Rule - 7
Di, tri, tetra, secondary, tertiary, and normal are not counted in
alphabetical order.

Note

Cyclo, iso, neo are counted in alphabetical order.

 ✓
Di, tri, tetra Iso
secondary, tertiary Neo
normal Cyclo
 Example

Write the IUPAC name of the following compound.

CH3 – CH – CH2 – CH3
CH2 – CH3

Solution
 Example

Write the IUPAC name of the following compound.

CH3
CH3 – C – CH2 – CH – CH3
CH3 CH3

Solution
 Example

Write the IUPAC name of the following compound.

Br Cl

Solution
 Some important Common names

Iso

Neo

Secondary

Tertiary.
 Example
Match the column : –
Compound Common names
OH
(A) (P) Sec-butyl alcohol
OH
(B) (Q) Isopropyl alcohol

(C) (R) Tert-butyl alcohol

OH
(D) (S) n-butyl alcohol
OH
(1) A → R, B → P, C → Q, D → S (2) B → Q, A → P, C → S, D → R
(3) A → Q, B → P, C → S, D → R (4) A → P, B → Q, C → S, D → R

Solution
Ans. 3
 IUPAC naming for Complex substituent

✓ When substituents or multiple bond are present in the substituent itself

which is attached to parent carbon chain.

✓ Numbering of subtituent always starts from that carbon atom which

is directly attached to parent carbon chain.

Example

1 3 5 7
2 4 6
1
2 4-(1–methylethyl)
Rule-1

✓ If substituent is complex type then their name is written in bracket.

Example

1 2 3 4 5 6 7 8
1. CH3 – CH2 – CH2 – CH – CH2 – CH2 – CH2 – CH3
1 CH – CH3
4-(1–methylethyl)octane
2 CH3

1 2 3 4 5 6 7 8
2. CH3 – CH2 – CH2 – CH – CH2 – CH2 – CH2 – CH3
1 H3C – C – CH3
4-(1, 1-dimethylethyl)octane
2 CH3
Rule-2

✓ When any complex substituent gets repeated more than one times then
we use : -

2 bis
3 tris
4 tetrakis
5 pentakis

Example

4,6 – Bis (1,1 – dimethylethyl) nonane

Rule-3

✓ If di, tri, tetra are used for complex substituent then they are consider for
alphabetical order.

Rule-4

✓ bis, tris, tetrakis are not consider for alphabetical order.

Example

Cl
3–chloro–4,6–Bis(1,1–dimethylethyl) nonane
IUPAC NOMENCLATURE
OF MULTIPLE BOND
 Selection of parent chain

Select that carbon chain (cyclic or acyclic) which includes : -

Maximum number > Longest Chain > Maximum number

of Multiple bond of substituent.
(= > )

Numbering in PCC :

Numbering always Starts from terminal C-atom.

Numbering should be done according to lowest set of locant rule (LSLR).

Follow LSLR in following order :

Multiple bond > Substituent > Alphabetical order

(= > )
 Example

Write IUPAC name of following compound ?

(1) (2)

But-1-ene
Or Pent-2-ene
Butene Or
Or 2-pentene
1-butene

(3) (4)

Prop-1-yne Hexa-1-en-4-yne
Or
1-propyne
 Example
yne
(5)

ene
Pent-1-en-4-yne

Note

If more than one type of multiple bonds are present in PCC then ‘a’ is written
after word root.

(6) CH3—CH2—CH2—CH2 —CH == CH2 (7)

|
CH == CH2
3-propylpenta-1,4-diene Hepta-3,5-dien-1-yne
 Example

Write IUPAC name of following compound ?

(1) CH3—CH2—CH2— C == CH2 2-methylpent-1-ene

|
CH3

(3) 2-(1-methylpropyl)buta-1,3-diene

3-Ethenylhexa-1,4-diene
(4)
 Substituents Sec. Prefix

=R alkylidene
=CH2 Methylene
=CH—CH3 Ethylidene
=CH—CH2—CH3 Propylidene
=CH—CH3 Isopropylidene
CH3 Or
1-methylethylidene

(5) 3-methylenehexa-1,5-diene
Example

(6)

3-Ethynylpenta-1,4-diene
 Example

The IUPAC name of the following compound is : [JEE Main 2019]

(1) 3,5-dimethyl-4-propylhept-6-en-1-yne
CH3
(2) 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne H3C CH
(3) 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
(4) 3,5-dimethyl-4-propylhept-1-en-6-yne CH3
CH2
Solution

Ans. (4)
 Example [JEE(Advanced) 1984]

The IUPAC name of the compound having the formula is :

CH3
|
H3 C – C – CH = CH2
|
CH3
(A) 3,3,3 trimethyl 1 propene (B) 1,1,1 trimethyl 2 propene
(C) 3,3 dimethyl 1 butene (D) 2,2 dimethyl 3 butene

Solution

Ans. (C)
 Example
[JEE(Advanced) 1987]
The IUPAC name of the compound CH2=CH–CH(CH3)2 is :
(A) 1,1 dimethyl 2 propene (B) 3 methyl 1 butene
(C) 2 vinyl propane (D) None of the above

Solution

Ans. (B)
 Example
[JEE(Advanced) 1989]
The number of sigma and pi bonds in 1 Butene 3 yne are:
(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi
(C) 8 sigma and 2 pi (D) 6 sigma and 4 pi

Solution

Ans. (B)
IUPAC NOMENCLATURE OF
CYCLIC HYDROCARBON
✓ IUPAC names of cyclic compounds are given by prefixing “cyclo” before
parent name.

Example

Cyclopropane

Cyclobutane

Cyclopentane
 Note

In case of cyclic hydrocarbon select that chain (whether cyclic or open

chain) as parent chain which contains more no. of carbon atom.

But

If both cycle and open chain contain same no. of carbon atom and same
subtituent then cycle will be considered as parent chain.

Example

1–pentylcyclopentane

Note Cyclic ring and aliphatic carbon chain are never considered
together for PCC.
Example

Cyclohexane

1,1,2,2–tetramethylcyclobutane

1,2,3,4–tetramethylcyclobutane
Example

Cl

1–bromo–3–chlorocyclopentane

Br

1–ethyl–4–methylcyclohexane

Me
Et
4–bromo–2–ethyl–1–methylcyclohexane

Br
 Example

1–cyclopentylcyclohexane

(1–ethylpropyl)cyclopentane
Example

cyclopentylethene

3
4 2
6–ethyl–3,3–dimethylcyclohex–1–ene
5 1
6

F
4
5 3
6 2 2–bromo–1–chloro–4–fluorocyclohexane
1 Br
Cl
 Special Case − 1

✓ If two or more than two cycles are attached by an open chain then open
chain will be considered as parent chain.

Example

Cyclobutylcyclopropylmethane

Parent chain
Parent chain

1–cyclohexyl–3–cyclopentylpropane
 Special Case − 2

✓ When a cycle attach with benzene then benzene always consider as

main chain.

Example

Cyclohexylbenzene
 Example

Write correct IUPAC name of following compounds.

Cyclohexa-1,3-diene 1,1-Dimethylcyclopropane

1-Ethyl-2-methylcyclopropane 3-Ethyl-6-methylcyclohexa-1,4-diene
Example

1-Propylcyclopropane 2-Cyclopropylbutane

2-ethyl-1,1,4-Trimethyl-cyclobutane
IUPAC NOMENCLATURE OF
MONOFUNCTIONAL GROUP
 Type-1

Functional group belong to 2 suffix category and they are carbon containing
and chain terminating.

O O O O
Ex: —C—OH, —C—H, —C—NH2, —C—X,
O O O
—C—O—R, —CN, —C—O—C—

Selection of parent chain : That carbon chain will be selected as parent

chain which contains carbon of functional group.

Numbering of parent chain : Numbering should be start from functional

group carbon.
 Type-2

Functional group belong to 2 suffix category and they are carbon containing
and chain non–terminating.
O
Ex: —C— (ketone)

Selection of parent chain : That carbon chain will be selected as parent

chain which contains carbons of such functional group.

Numbering of parent chain : Numbering should be done from that end

which gives lowest locant no. of functional group carbon.
 Type-3
Functional group belong to 2 suffix category and do not contain carbon.

Ex: —OH, —NH2, —SH, —SO3H

Selection of parent chain : Select that carbon chain as parent chain which
contains carbon with which such functional groups are attached.

Numbering of parent chain : Numbering should be done from that end

which gives lowest locant no. of that carbon.
 ✓ Priority order of functional group’s for IUPAC Nomenclature

Functional group Prefix (2°) Suffix (2°)

O
(1)
—C—OH X oicacid
Carbon include in PCC
—COOH Carboxy Carboxylicacid

(2) —SO3H Sulpho Sulphonic acid

 Functional group Prefix (2°) Suffix (2°)
O
Oic anhydride
—C
(3) O X
—C
O
O
—C
O X Carboxylic anhydride
—C
O
O
X alkyl……..oate
(4) —C—OR
—COOR Alkoxy carbonyl alkyl……carboxylate
—OCOR Alkanoyl oxy X
Functional group Prefix (2°) Suffix (2°)

O
X Oyl halide
(5) —C—X

Halocarbonyl/ Carbonyl halide

—COX
haloformyl
O
X amide
(6) —C—NH2

carbamoyl Carboxamide
—CONH2

(7) —CN X Nitrile

—CN Cyano Carbonitrile

Functional group Prefix (2°) Suffix (2°)

→ isocyano Carbylamine
(8) —N==C
or
carbylamino

O
(9) —C—H oxo al

—CHO formyl Carbaldehyde

 Functional group Prefix (2°) Suffix (2°)

O Keto/oxo
(10)
—C— one

(11) —OH Hydroxy ol

(12) —SH mercapto thiol

(13) —NH2 amino amine

(1) CARBOXYLIC ACIDS (-COOH)

O Prefix Suffix

—C—OH X Oic acid

—COOH Carboxy Carboxylic acid

Example

O Ethanoic acid
H3C—C—OH (Acetic acid)

But-2-enoic acid
CH3—CH=CH—COOH (Crotonic acid)
Example
Ethane-1,2-dioic acid
COOH or
COOH Ethanedioic acid (Oxalic acid)

OH 2-Ethylprop-2-en-1-oic acid

CH2 O
3-Methylenepent-4-enoic acid
OH
𝐒𝐩𝐞𝐜𝐢𝐚𝐥 𝐂𝐚𝐬𝐞 − 𝟏

✓ When Carbon containing chain terminating functional group is directly

attached to the ring then cycle is consider as parent chain.

Example

COOH

Cyclohexanecarboxylic acid

COOH

Cyclopent-2-ene-1-carboxylic acid
 Example [JEE Main 2020]
The IUPAC name of the following compound is :
CH3 O
(1) 3-Bromo-1, 2-dimethylbut-1-ene
(2) 5-Bromo-3-methylcyclopentanoic acid C—OH

(3) 3-Bromo-5-methylcyclopentane carboxylic acid

(4) 3-Bromo-5-methylcyclopentanoic acid Br
Solution

Ans. (1)
 𝐒𝐩𝐞𝐜𝐢𝐚𝐥 𝐂𝐚𝐬𝐞 − 2

✓ When more than two carbon containing functional groups are directly
connected to parent carbon chain.

Example

COOH

Propane-1,2,3-tricarboxylic acid
COOH COOH
(2) CARBOXYLIC ACID ANHYDRIDE

Prefix Suffix

O
—C X Oic anhydride
O
—C
O

O
—C
O X Carboxylic anhydride
—C
O
Example

O O
Methanoic anhydride
C C
H O H

O O
C C Ethanoic anhydride
H3C O CH3

O
O O Butane-1,4-dioic anhydride
(Succinic anhydride)
Example

O
C
But–2–ene–1,4–dioicanhydride
O
C
O

O
Pentane-1,5-dioic anhydride
O
(3) ESTER

Prefix Suffix
O
—C—OR X alkyl……..oate

—COOR alkoxy carbonyl alkyl……carboxylate

O C R alkanoyloxy X

Naming Formate R—O—C—R

O
Alkyl Alkanoate
Example

O
C CH3 Methylethanoate
H3C O

O
C CH3 Methylmethanoate
H O

O
H3C C CH3
Methyl-2-bromopropanoate
CH O

Br
Example

O
C O Cyclopropylcyclopro-2-ene-1-carboxylate

O
Propyl-2-methylpentanoate
O
(4) ACID HALIDE

Prefix Suffix

O
—C—X X Oyl halide

—COX haloformyl Carbonyl halide

Example

CH3—C—Cl Ethanoyl chloride

O

CH3—CH=CH—C—Br But-2-enoyl bromide

O

O
2-Ethylprop-2-en-1-oylchloride
Cl
Example

O
Cl

2-cyclohexylethanoylchloride

Cl Cyclohexanecarbonyl chloride
 (5) AMIDE

Prefix Suffix
O
—C—NH2 X amide

—CONH2 carbamoyl Carboxamide

Example

O
1. C Ethanamide (Acetamide)
H3C NH2
Example

H3C—NH—CHO N-Methylmethanamide

NH2 Cyclohexanecarboxamide

Cl
N
4-Chloro-N,N,5-trimethylhex-3-enamide
O
Example

NH2 Benzenecarboxamide
Or
Benzamide

O
CH3
C6H5 N N-methylbenzamide

H
(6) CYANIDE (-CN)

Prefix Suffix

—CN X Nitrile

—CN Cyano Carbonitrile

Example

CH3—CN Ethanenitrile (methyl cyanide)

CH3—CH2—CH2—CN Butanenitrile

CN
Cyclobutanecarbonitrile
Example

CN
Benzenecarbonitrile
Or
Benzonitrile

H3C
CN

NC CN
CN CH3
 →
(7) isocyanide (—N=C)

Prefix Suffix

→ isocyano Carbylamine
—N==C
or
carbylamino
Example

NC

2–methylcyclohexane–1–carbylamine

Cyclopropane–1,2–dicarbylamine
CN NC
(8) ALDEHYDE (-CHO)

Prefix Suffix

O
—C—H oxo al

—CHO formyl Carbaldehyde

Example

OHC—CH=CH2 Prop-2-enal or
2-Propenal (Acrylaldehyde)

But-2-enal or
OHC—CH=CH—CH3
2-Butenal (Crotonaldehyde)
Example

O O
Pentanedial
H H

O
3-methyl-3-pentenal
H
(9) KETONE

Prefix Suffix
O
—C— Keto/oxo one

Example

O
Propanone (Acetone)
C
H3C CH3

O
Pentan-2-one
Example

Cyclopentanone

4-Bromocyclopent-2-enone

Br
O

3-(1,1,-dimethylethyl)-4-(1-methylethyl)cyclopentanone
(10) Sulphonic acid (–SO3H)

Prefix Suffix

—SO3H sulpho Sulphonic acid

Example

SO3H Propane–1–sulphonicacid

SO3H

4,4–dimethylcyclohexane–1–sulphonicacid
 (11) ALCOHOL (–OH)

Prefix Suffix

—OH Hydroxy ol

Example
Methanol
CH3—OH (Methyl alcohol / Wood spirit)

Ethanol
CH3—CH2—OH (Ethyl alcohol / Grain alcohol)

H3C—CH2—C—CH2—OH 2–Ethylprop–2–en–1–ol
CH2
Example

CH2
Cl—CH2—CH—C—CH3 1-Chloro-3-methylbut-3-en-2-ol

OH

OH
3,4-Dimethyl-1-penten-3-ol

OH Propane-1,2,3-triol or
HO—CH2—CH—CH2—OH 1,2,3-Propanetriol (Glycerol/Glycerine)
 (13) AMINE (-NH2)

Prefix Suffix
—NH2 amino amine

Example

H2N—CH2—CH2—CH3 Propan-1-amine

H2C—CH2—CH2—CH2—NH—CH2—CH3 N-Ethylbutan-1-amine

CH3
H3C—CH2—CH2—N—CH2—CH3 N-Ethyl-N-methylpropan-1-amine
 R—O—R

Ether (R-O-R) Alkoxy Alkane

Prefix Suffix
—OR Alkoxy 

Example

1 2
H3C—O—CH2—CH3 Methoxyethane

2 1
H3C—O—CH—CH3 2-Methoxypropane
3CH
3

1 2
H3C—O—CH2—CH2—O—CH3 1,2-Dimethoxyethane
 Example

The IUPAC name of the following compound is :

O
CH3
CH3
CH3
Mesityl oxide(common name)

Solution

Ans. 4-methylpent-3-en-2-one