■ CHEMISTRY | STANDARD X

Nomenclature of Organic Compounds &

Isomerism
Chapter 1 · Complete Study Notes

■ ■ ■■ ■
Alkanes Alkenes Alkynes Isomerism

Saturated hydrocarbons One C=C double bond One C≡C triple bond Same formula, different
Suffix: -ane Suffix: -ene Suffix: -yne structures

IUPAC NAMING — ALKANES (SATURATED)

■ The longest continuous carbon chain is the main chain. Remaining carbons are branches (substituents).

Formula for naming branched alkanes:

Position No. of Branch + hyphen + Name of Alkyl Group + Word Root + suffix (ane)

Step-by-step rules:
1 Identify the longest carbon chain → main chain.

2 Number the chain so branches get the lowest position numbers.

3 If two directions give the same lowest number for the first branch, choose the direction giving the lowest
number for the second branch.

4 If the same branch occurs more than once, use prefixes: di (2), tri (3), tetra (4) and separate position
numbers with commas.

5 List branch names in alphabetical order (ignore multiplying prefixes).

Worked examples:
Main Chain
Structural Formula Branch / Position IUPAC Name
(C)

CH3–CH(CH3)–CH2–CH3 4 Methyl at C-2 2-Methylbutane

CH3–CH2–CH(CH3)–CH2–CH3 5 Methyl at C-3 3-Methylpentane

CH3–C(CH3)2–CH2–CH3 4 Two methyls at C-2 2,2-Dimethylbutane

CH3–CH(CH3)–CH2–CH(CH3)–CH2–CH3 6 Methyl at C-2 & C-4 2,4-Dimethylhexane

CH3–CH(CH3)–CH2–CH2–CH(CH3)–CH3 7 Methyl at C-2 & C-5 2,5-Dimethylheptane

IUPAC NAMING — UNSATURATED HYDROCARBONS

Alkenes (C=C double bond) — suffix: -ene

■ Number the chain so the double-bond carbons get the lowest position number. State position of the double
bond before the suffix.

Word Root + hyphen + Position of double bond + hyphen + ene

Formula IUPAC Name Reason

CH2=CH–CH2–CH3 But-1-ene Double bond at C-1

CH3–CH=CH–CH3 But-2-ene Double bond at C-2

CH2=CH2 Ethene 2C, double bond

CH3–CH2–CH=CH2 But-1-ene Double bond at C-1

CH3–CH2–CH=CH–CH3 Pent-2-ene Double bond at C-2

Alkynes (C≡C triple bond) — suffix: -yne

Word Root + hyphen + Position of triple bond + hyphen + yne

Formula IUPAC Name Notes

CH≡C–CH2–CH3 But-1-yne Triple bond at C-1

CH3–C≡C–CH3 But-2-yne Triple bond at C-2

CH≡CH Ethyne (Acetylene) Simplest alkyne

FUNCTIONAL GROUPS — NOMENCLATURE

■ A functional group is an atom or group of atoms bonded to carbon that gives an organic compound its
characteristic chemical and physical properties.

Functional
Name Class IUPAC Suffix / Rule Example
Group

–OH Hydroxyl Alcohol alkane–e + ol (position before 'ol') Propan-1-ol

–COOH Carboxyl Carboxylic acid alkane–e + oic acid Ethanoic acid

–CHO Aldehydic Aldehyde alkane–e + al Ethanal

alkane–e + one (position before

>C=O Keto Ketone Pentan-2-one
'one')

Shorter alkyl = alkoxy Longer alkyl =

–O–R Alkoxy Ether Methoxyethane
alkane

–F, –Cl, Position + fluoro/chloro/ bromo/iodo

Halo Halo compound 1-Chloropropane
–Br, –I + alkane

Alcohol (–OH) naming detail:

alkane – e + hyphen + position no. of –OH + hyphen + ol

Formula IUPAC Name

CH3–OH Methanol

CH3–CH2–OH Ethanol
 CH3–CH2–CH2–OH Propan-1-ol

CH3–CH(OH)–CH3 Propan-2-ol

CH3–CH2–CH2–CH2–OH Butan-1-ol

ISOMERISM

■ Compounds having the same molecular formula but different chemical and physical properties are called
isomers. This phenomenon is called isomerism.

■ Chain Isomerism ■ Position Isomerism ■ Functional Group Isomerism

Same molecular formula but differ in Same molecular formula & same Same molecular formula but differ in
the structure of the carbon chain functional group, but differ in the the type of functional group.
(branching). position of the functional group.
CH3–CH2–OH (Ethanol) vs
CH3–CH2–CH2–CH3 vs CH3–CH2–CH2–OH vs CH3–O–CH3 (Methoxymethane) (Both:
CH3–CH(CH3)–CH3 (Both: C4H10) CH3–CH(OH)–CH3 (Both: C3H8O) C2H6O)

Chain isomers of Pentane (C5H12):

# Structural Formula IUPAC Name

1 CH3–CH2–CH2–CH2–CH3 Pentane

2 CH3–CH(CH3)–CH2–CH3 2-Methylbutane

3 CH3–C(CH3)2–CH3 2,2-Dimethylpropane

WORD ROOTS & QUICK REFERENCE

Carbon-chain word roots (C1 – C10):

C atoms Word Root Alkane Alkene Alkyne

1 Meth- Methane — —

2 Eth- Ethane Ethene Ethyne

3 Prop- Propane Propene Propyne

4 But- Butane But-1-ene/ But-2-ene But-1-yne/ But-2-yne

5 Pent- Pentane Pent-1-ene Pent-1-yne

6 Hex- Hexane Hex-1-ene Hex-1-yne

7 Hept- Heptane Hept-1-ene Hept-1-yne

8 Oct- Octane Oct-1-ene Oct-1-yne

9 Non- Nonane Non-1-ene Non-1-yne

10 Dec- Decane Dec-1-ene Dec-1-yne

General molecular formulas:

Class General Formula Suffix Bond type

Alkane CnH(2n+2) -ane Single (C–C)

Alkene CnH(2n) -ene Double (C=C)

Alkyne CnH(2n-2) -yne Triple (C≡C)

Memory Tips ■

■ For alcohols: think Propan-1-ol → –OH is on carbon 1.

■ For ketones: the keto group is never at C-1 or the last C (that would be an aldehyde).

■ For ethers: shorter alkyl = alkoxy prefix, longer alkyl = alkane base name.

■ Chain isomers: same formula, different carbon skeleton.

■ Position isomers: same skeleton & same group, different position.

■ Functional group isomers: same formula but different type of group.

FUNCTIONAL ISOMERISM & METAMERISM

■ When compounds have the same molecular formula but different functional groups, they are known as
functional isomers. This phenomenon is called functional isomerism.

Examples of Functional Isomers:

Co
mpo Structural Formula Functional Group IUPAC Name
und

i CH3–CH2–CHO Aldehydic (–CHO) Propanal

ii CH3–CO–CH3 Keto (>C=O) Propanone

iii CH3–CH2–OH Hydroxyl (–OH) Ethanol

iv CH3–O–CH3 Alkoxy (–O–R) Methoxymethane

v CH3–CH2–CH2–CHO Aldehydic (–CHO) Butanal

vi CH3–CH2–CO–CH3 Keto (>C=O) Butan-2-one

METAMERISM

■ Compounds having the same molecular formula but different alkyl groups attached to either side of the
functional group (bivalent group: –O–, >C=O) are called metamers. This phenomenon is metamerism.

■ Note: Metamers are also examples of position isomers. Metamerism arises only in compounds with bivalent
functional groups such as ethers (–O–) and ketones (>C=O).

Examples of Metamers (Ethers — C4H10O):

Co
mpo Structural Formula Alkyl groups on either side of –O– IUPAC Name
und

i CH3–CH2–O–CH2–CH3 Ethyl & Ethyl (same) Ethoxyethane

ii CH3–O–CH2–CH2–CH3 Methyl & Propyl (different) Methoxypropane

Examples of Metamers (Ketones — C5H10O):

Co
mpo Structural Formula Alkyl groups on either side of >C=O IUPAC Name
und
 i CH3–CH2–CO–CH2–CH3 Ethyl & Ethyl (same) Pentan-3-one

ii CH3–CO–CH2–CH2–CH3 Methyl & Propyl (different) Pentan-2-one

ALL 4 TYPES OF ISOMERISM — SUMMARY

Same molecular
Type What differs? Example pair
formula?

Butane vs 2-Methylpropane
Chain Isomerism ✔ Yes Carbon skeleton (branching)
(C4H10)

Propan-1-ol vs Propan-2-ol
Position Isomerism ✔ Yes Position of the functional group
(C3H8O)

Functional Group Ethanol vs Methoxymethane

✔ Yes Type of functional group
Isomerism (C2H6O)

Alkyl groups on either side of Ethoxyethane vs

Metamerism ✔ Yes
bivalent group Methoxypropane (C4H10O)

Chemistry Standard X · Chapter 1: Nomenclature of Organic Compounds & Isomerism · Study Notes