Which of the following is the correct IUPAC name? (i) 3-Ethyl-4,4-dimethylheptane (ii) 4,4-Dimethyl-3-ethylhep

NCERT Exemplar · Q1

Q. Which of the following is the correct IUPAC name?

(i) 3-Ethyl-4,4-dimethylheptane

(ii) 4,4-Dimethyl-3-ethylheptane

(iii) 5-Ethyl-4,4-dimethylheptane

(iv) 4,4-Bis(methyl)-3-ethylheptane

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Concept understanding — Chain Isomerism

Chain Isomerism: The Skeleton of a Molecule

Imagine you have a set of 5 identical Lego bricks. You can snap them together in a straight line — one after the other — to make a long, thin rod. Or, you could take the same 5 bricks and make a "T" shape: a straight chain of 4 bricks, with the 5th brick attached to the middle one. Both structures use exactly the same number and type of bricks, but their shapes are different.

That difference in shape — specifically, in the carbon skeleton — is the heart of chain isomerism.

The Intuition

Carbon atoms love to bond with each other to form chains. But they don't always have to form a single, straight line. They can branch off. When two molecules have the same molecular formula (same number of each atom) but differ in how their carbon atoms are connected — one is a straight chain, another is branched — they are chain isomers.

Think of it like a family tree. The same set of people can be arranged in a direct line (grandparent → parent → child) or with branches (grandparent has two children, each with their own children). The "people" (carbon atoms) are the same, but the "connections" (bonds) form different patterns.

The Precise Statement

Chain isomerism is a type of structural isomerism where two or more compounds have the same molecular formula but differ in the arrangement of the carbon skeleton (the carbon chain). This difference arises because the carbon atoms can be linked in a straight chain or in one or more branched chains.

Important

Chain isomers always have the same molecular formula but different structural formulas due to different carbon skeletons. They are distinct compounds with different physical and chemical properties.

A Concrete Example: Pentane ( $C_5H_{12}$ )

The molecular formula $C_5H_{12}$ can represent three different chain isomers. Let's draw them:

n-Pentane (normal pentane): A straight chain of 5 carbons.

CH_3-CH_2-CH_2-CH_2-CH_3

Isopentane (2-methylbutane): A chain of 4 carbons with a 1-carbon branch (a methyl group, $-CH_3$ ) attached to the second carbon.

CH_3-CH(CH_3)-CH_2-CH_3

Neopentane (2,2-dimethylpropane): A central carbon bonded to four other carbons — a highly branched structure.

C(CH_3)_4

Isomer Name	Common Name	Structure (Condensed)	Boiling Point (°C)
Pentane	n-Pentane	$CH_3(CH_2)_3CH_3$	36.1
2-Methylbutane	Isopentane	$(CH_3)_2CHCH_2CH_3$	27.7
2,2-Dimethylpropane	Neopentane	$C(CH_3)_4$	9.5

Notice how the boiling point drops as the molecule becomes more branched. This is because branching reduces the surface area available for intermolecular forces (London dispersion forces), making the molecule easier to vaporize.

Watch out

A common mistake is to think that any difference in structure is chain isomerism. It is only about the carbon skeleton. If two molecules have the same skeleton but different positions of a double bond or a functional group, that is a different type of isomerism (position isomerism), not chain isomerism.

When Does Chain Isomerism Occur?

Chain isomerism is possible only when the carbon chain is long enough to allow branching. For alkanes:

Methane ( $CH_4$ ), Ethane ( $C_2H_6$ ), Propane ( $C_3H_8$ ): No chain isomers. There is only one way to arrange the carbons.
Butane ( $C_4H_{10}$ ): Two chain isomers (n-butane and isobutane).
Pentane ( $C_5H_{12}$ ): Three chain isomers (as shown above).
The number of possible chain isomers increases rapidly as the number of carbon atoms increases.

Why Does This Matter?

Chain isomers are different compounds. They have different:

Physical properties: Boiling point, melting point, density.
Chemical reactivity: The branching affects how easily the molecule reacts in certain reactions (e.g., combustion, halogenation).
Biological activity: In organic chemistry and biochemistry, the shape of a molecule determines how it interacts with enzymes and receptors. A branched isomer might be a drug, while its straight-chain isomer might be inactive or even toxic.

So, when you see a molecular formula like $C_6H_{14}$ , don't just think "hexane." Ask yourself: How many different ways can I arrange these six carbon atoms? That question is the beginning of understanding chain isomerism.

If you've searched "Chain Isomerism class 11 chemistry notes" or "Chain Isomerism NCERT solutions", this page covers exactly that ground — the concept is a standard part of the Class 11 Chemistry NCERT/CBSE syllabus. It also carries real weight in JEE Main, NEET and state CET Chemistry papers, where questions on chain isomerism test both conceptual understanding and calculation speed.

The key is to number the longest carbon chain so that substituents get the lowest locant set (lowest number at the first point of difference). For the given structure, the correct IUPAC name is 3-Ethyl-4,4-dimethylheptane, which corresponds to option (i).

Identify the longest carbon chain.

The parent chain must be the longest continuous carbon chain. In this molecule, the longest chain has 7 carbons — a heptane. Any branching off this chain are substituents.
Number the chain to give the lowest locants.

IUPAC rules say: number from the end that gives the substituents the smallest possible numbers at the first point of difference.
- If you number from left to right, the substituents appear at positions 3 (ethyl) and 4,4 (two methyl groups).
- If you number from right to left, the substituents appear at positions 4 (ethyl) and 4,4 (two methyl groups) — but here the first point of difference is at position 3 vs. 4, so left-to-right wins.
List substituents in alphabetical order.

Alphabetical order ignores prefixes like di-, tri-, etc. So "ethyl" comes before "methyl". The name becomes: 3-ethyl-4,4-dimethylheptane.
Check the options.
- (i) 3-Ethyl-4,4-dimethylheptane — matches our result.
- (ii) 4,4-Dimethyl-3-ethylheptane — same locants but wrong order (ethyl should come first alphabetically).
- (iii) 5-Ethyl-4,4-dimethylheptane — numbering from the wrong end gives higher locants.
- (iv) 4,4-Bis(methyl)-3-ethylheptane — "bis(methyl)" is not standard; "dimethyl" is correct.

Watch out

A common mistake is to number from the end that gives the lowest sum of locants, but IUPAC uses the first point of difference rule. Here, both numbering directions give a sum of 11 (3+4+4 vs. 4+4+4), so the sum doesn't help — you must compare the first number that differs: 3 vs. 4.

Tip

When substituents are the same (like two methyls), use the prefixes di-, tri-, etc., but keep them in alphabetical order with other substituents. "Ethyl" before "dimethyl" because 'e' comes before 'm'.

Note

The printed NCERT Exemplar answer key gives option (ii) (4,4-Dimethyl-3-ethylheptane). That name lists the substituents in the wrong order: IUPAC cites substituents alphabetically, so ethyl must come before methyl — exactly as the textbook's own §8.5.2 worked example (3-ethyl-4,4-dimethylheptane) shows. The chemically correct name is option (i).

✓Final answer

The correct IUPAC name is 3-Ethyl-4,4-dimethylheptane, option (i) .

Same / Similar Concept — real previous-year questions on the same or a closely similar concept, not this exact question.

CBSE 2026Set ANNUAL1 mark
$Q. Write the isomers of pentane.$
›Reveal solutionSolution
Pentane (C5H12) has exactly three chain (structural) isomers: n-pentane, isopentane, and neopentane.

All three isomers share the same molecular formula, C5H12, but differ in how the 5 carbons are connected:

n-Pentane: CH3-CH2-CH2-CH2-CH3 — a straight, unbranched chain of 5 carbons.

Isopentane (2-methylbutane): (CH3)2CH-CH2-CH3 — a 4-carbon main chain (butane) with one methyl branch on C2.

Neopentane (2,2-dimethylpropane): C(CH3)4 — a central carbon bonded to four methyl groups, i.e., a 3-carbon main chain (propane) with two methyl branches, both on C2.

These differ in physical properties too (e.g., boiling point decreases as branching increases: n-pentane 36 C is greater than isopentane 28 C which is greater than neopentane 9.5 C), because more compact, branched molecules have less surface contact and weaker van der Waals forces between molecules.

✓Final answer
$Pentane's three isomers: n-pentane, isopentane (2-methylbutane), and neopentane (2,2-dimethylpropane).$
CBSE 2024Set ANNUAL1 markMCQ
$Q. CH3-CH(CH3)-CH2-CH2-CH3 is$
(a) Isopentane
(b) Neopentane
(c) Isohexane
(d) n-pentane
›Reveal solutionSolution
Counting all carbons in CH3-CH(CH3)-CH2-CH2-CH3 gives 6 total, so this is a hexane isomer (2-methylpentane), commonly called isohexane, not isopentane (which only has 5 carbons).

Structure: CH3-CH(CH3)-CH2-CH2-CH3

Count the carbons: the main chain CH3-CH-CH2-CH2-CH3 has 5 carbons, plus the branch -CH3 on the second carbon adds 1 more, for a total of 6 carbons -- this is a hexane (C6H14) isomer.

IUPAC name: numbering the main chain to give the substituent the lowest locant, the methyl group is on C2, giving 2-methylpentane.

Common names for the pentane/hexane isomers:

n-pentane = straight-chain C5H12.

Isopentane = 2-methylbutane, C5H12 (5 carbons total).

Neopentane = 2,2-dimethylpropane, C5H12 (5 carbons total).

Isohexane = 2-methylpentane, C6H14 (6 carbons total) -- this matches our compound.

✓Final answer
$(c) Isohexane.$
CBSE 2023Set ANNUAL1 markMCQ
$Q. Which among the following is an isomeric pair$
(a) Propane and Propene
(b) Butane and 2-methyl propane
(c) Pentane and propane
(d) Butane and Isopropane
›Reveal solutionSolution
Butane and 2-methylpropane are chain isomers (both C4H10).

Isomers are compounds with the same molecular formula but different arrangements of atoms. Checking the pairs:

Butane: CH3-CH2-CH2-CH3, formula C4H10

2-methylpropane (isobutane): (CH3)3CH, formula C4H10 Both have the molecular formula C4H10 but differ in carbon-chain branching, so they are chain isomers. The other pairs have different molecular formulae (e.g. propane C3H8 vs propene C3H6), so they are not isomers.

Structural isomerism is introduced in the NCERT/CBSE Class 11 Chemistry chapter Organic Chemistry - Some Basic Principles and Techniques.

✓Final answer
$(b) Butane and 2-methyl propane.$
CBSE 2018Set annual21 markMCQ
$Q. The structure of Isobutane is:$
(a) CH3-CH2-CH3
(b) CH3-CH(CH3)-CH3
(c) CH3-CH3
(d) CH4
›Reveal solutionSolution
Isobutane is 2-methylpropane — a central CH carbon flanked by three methyl groups — distinguishing it from the straight-chain propane, ethane, and methane shown in the other options.

Isobutane (also called 2-methylpropane, molecular formula C4H10) is the branched-chain structural isomer of n-butane. Its structure has a central carbon atom bonded to three -CH3 (methyl) groups and one hydrogen atom:

CH3-CH(CH3)-CH3, i.e., a central CH carbon with three methyl substituents (equivalent to writing (CH3)3CH).

Checking the other options:

(a) CH3-CH2-CH3 is propane (C3H8), a straight-chain 3-carbon alkane — not isobutane.

(c) CH3-CH3 is ethane (C2H6), a 2-carbon alkane.

(d) CH4 is methane, a 1-carbon alkane.

Only option (b) has the branched, 4-carbon skeleton (one central carbon bonded to three methyl groups) that defines isobutane.

✓Final answer
$The correct option is (b) CH3-CH(CH3)-CH3 — the branched structure of isobutane (2-methylpropane), with a central carbon bonded to three methyl groups.$
CBSE 2018Set annual21 markMCQ
$Q. The number of chain isomers in Hexane is:$
(a) 4
(b) 5
(c) 3
(d) 6
›Reveal solutionSolution
Counting every distinct way to arrange six carbons into a chain, with or without branches, gives exactly five different hexane skeletons.

Chain (structural) isomers of an alkane are compounds with the same molecular formula but different arrangements (connectivity) of the carbon skeleton. For hexane, C6H14, the five possible chain isomers are:

n-Hexane: CH3-CH2-CH2-CH2-CH2-CH3 (straight chain)

2-Methylpentane: (CH3)2CH-CH2-CH2-CH3

3-Methylpentane: CH3-CH2-CH(CH3)-CH2-CH3

2,2-Dimethylbutane: (CH3)3C-CH2-CH3

2,3-Dimethylbutane: (CH3)2CH-CH(CH3)2

Each of these has the same molecular formula (C6H14) but a distinct carbon skeleton (different branching pattern), making them chain/structural isomers of one another. No sixth distinct arrangement of 6 carbons exists without repeating one of these five skeletons.

✓Final answer
$The correct option is (b) 5 — hexane has exactly 5 chain isomers (n-hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, 2,3-dimethylbutane).$

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Q.Which of the following is the correct IUPAC name?

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