Q.Draw the structures of all the eight structural isomers that have the molecular formula C5H11Br. Name each isomer according to IUPAC system and classify them as primary, secondary or tertiary bromide.
Concept understanding — Structural Isomerism
Structural Isomerism: The First Meeting
Imagine you have a box of identical Lego bricks — four red, ten blue, and six yellow. You build two different models: a car and a house. Both use exactly the same number of each colour brick, but the structures are completely different. That is the core idea of isomerism: same atoms, different arrangement.
In chemistry, molecules are not just a list of atoms. How those atoms are connected matters enormously. Two molecules can have the exact same molecular formula (same number of each atom) but be connected in different ways. Those are structural isomers (also called constitutional isomers).
The Precise Statement
Structural isomers are compounds that have the same molecular formula but different connectivity of atoms — that is, different structural formulas.
The key word is connectivity. Which atom is bonded to which? If you change that, you get a different substance with different physical and chemical properties.
A Concrete Example: C₄H₁₀
Take butane, C₄H₁₀. There are exactly two ways to connect four carbon atoms and ten hydrogen atoms:
- n-Butane — a straight chain: C–C–C–C
- Isobutane (2-methylpropane) — a branched chain: a central carbon bonded to three methyl groups
Both have formula C₄H₁₀. But n-butane boils at –0.5 °C, while isobutane boils at –11.7 °C. Same atoms, different connectivity → different substance.
Structural isomers are not the same molecule. They are distinct compounds that happen to share a molecular formula. You cannot rotate or flip one to get the other — you must break and reform bonds.
The Three Main Types
Structural isomerism comes in three flavours:
| Type | What changes | Example (C₃H₆O) |
|---|---|---|
| Chain isomerism | The carbon skeleton (straight vs. branched) | Butane vs. isobutane |
| Position isomerism | The location of a functional group or substituent | Propan-1-ol vs. propan-2-ol (OH on carbon 1 vs. carbon 2) |
| Functional group isomerism | The atoms are rearranged into a different functional group | Propanal (aldehyde) vs. propanone (ketone) — both C₃H₆O |
Do not confuse structural isomers with stereoisomers. Stereoisomers have the same connectivity but differ in spatial arrangement (like left and right hands). That is a completely different chapter. For now: structural isomers = different bond connections.
Why This Matters
Structural isomers can have wildly different properties. Ethanol (C₂H₆O) is a drinkable alcohol; its isomer dimethyl ether is a gas used as a refrigerant. Same atoms, but one is a liquid you can consume, the other is a gas that would kill you. That is why chemists care so much about connectivity — it determines everything.
Quick Check
Question: Are these structural isomers?
Molecule A: CH₃–CH₂–CH₂–CH₃
Molecule B: CH₃–CH(CH₃)–CH₃
Answer: Yes. Both are C₄H₁₀. A is n-butane (straight chain), B is isobutane (branched). Different connectivity → structural isomers.
The molecular formula must be identical. If the formulas differ, they are not isomers at all — just different compounds.
Structural isomerism is introduced in the NCERT/CBSE Class 11 Chemistry chapter on Organic Chemistry: Some Basic Principles and Techniques, and ‘structural isomerism examples class 11’ is a frequently searched important-question topic for board exams, JEE Main and NEET. Correctly distinguishing structural isomers by connectivity, rather than just matching molecular formulas, is a skill tested throughout competitive organic chemistry exams.
Why this formula?
Structural Isomerism: Why the Key Ideas Hold
Structural isomerism arises when molecules share the same molecular formula but differ in the connectivity of atoms. There is no single "formula" for structural isomerism — instead, the key is understanding why different arrangements are possible.
The Core Principle: Connectivity ≠ Composition
A molecular formula tells you how many of each atom are present, but not how they are joined. Structural isomers exist because atoms can form bonds in multiple distinct sequences while satisfying valency rules.
Why This Happens: The Valency Constraint
Each atom has a fixed bonding capacity (valency):
- Carbon: 4 bonds
- Hydrogen: 1 bond
- Oxygen: 2 bonds
- Nitrogen: 3 bonds
Example: For C4H10, the formula satisfies 4(4)+10(1)=26 valence electrons. But the carbon atoms can be arranged as:
- A straight chain: CH3−CH2−CH2−CH3 (n-butane)
- A branched chain: CH3−CH(CH3)−CH3 (isobutane)
Both satisfy valency, but the connectivity differs.
The "Formula" for Counting Isomers: Why It's Not Simple
There is no closed-form formula to count structural isomers for a given molecular formula. The number grows rapidly and depends on:
- Carbon skeleton branching possibilities
- Functional group positions
- Ring formation possibilities
Why No Simple Formula Exists
The problem is combinatorial — the number of possible trees (acyclic graphs) with n carbon atoms grows exponentially. For example:
- C4H10: 2 structural isomers
- C5H12: 3 structural isomers
- C6H14: 5 structural isomers
- C10H22: 75 structural isomers
The pattern follows Cayley's formula for trees, but even that counts only carbon skeletons — not functional group positions.
Key Reasoning: The Branching Principle
The fundamental reason structural isomers exist is that carbon chains can branch. Consider C5H12:
- Straight chain: C−C−C−C−C (n-pentane)
- One branch: C−C−C(C)−C (isopentane) — the branch can be at position 2 or 3, but these are identical due to symmetry
- Two branches: C−C(C)(C)−C (neopentane) — a quaternary carbon
Why position matters: The branch location changes the carbon's environment, altering physical and chemical properties.
The Functional Group Position Rule
For compounds with functional groups (e.g., alcohols CnH2n+2O), the position of the -OH group creates isomers:
- CH3CH2CH2OH (propan-1-ol) — OH at end
- CH3CH(OH)CH3 (propan-2-ol) — OH in middle
Why these are distinct: The OH group's position changes the carbon's hybridization environment and the molecule's polarity.
The Ring-Chain Isomerism Reason
For unsaturated formulas like C4H8, the same formula can represent:
- A straight alkene: CH2=CH−CH2−CH3
- A branched alkene: CH3−C(=CH2)−CH3
- A cycloalkane: cyclobutane (ring)
Why rings form: Carbon atoms can bond to form closed loops, reducing the number of hydrogen atoms needed. The formula CnH2n can be either an alkene (one double bond) or a cycloalkane (one ring).
Summary: The Takeaway
| Aspect | Why It Holds |
|---|---|
| Different connectivity | Atoms can bond in multiple sequences while satisfying valency |
| No simple counting formula | The number of possible trees grows combinatorially |
| Branching creates isomers | Carbon chains can have branches at different positions |
| Position matters | Functional groups at different locations change properties |
| Rings vs. chains | Same formula can represent open chains or closed rings |
The key insight: Structural isomerism exists because molecular formula is a constraint, not a blueprint — it tells you the ingredients, not the recipe.
Concept: Structural Isomerism (chain and position isomers for alkyl halides).
Reasoning:
- The formula C5H11Br corresponds to a saturated alkyl bromide. The carbon skeleton can be a straight chain or branched.
- For each unique carbon skeleton, place the bromine atom on every distinct carbon atom. Each distinct position gives a different structural isomer.
- Classify each isomer based on the carbon to which Br is attached: primary (1°), secondary (2°), or tertiary (3°).
The eight isomers are:
- 1-Bromopentane (1°) — CH3CH2CH2CH2CH2Br
- 2-Bromopentane (2°) — CH3CH2CH2CHBrCH3
- 3-Bromopentane (2°) — CH3CH2CHBrCH2CH3
- 1-Bromo-2-methylbutane (1°) — CH3CH2CH(CH3)CH2Br
- 2-Bromo-2-methylbutane (3°) — CH3CH2CBr(CH3)2
- 2-Bromo-3-methylbutane (2°) — CH3CH(CH3)CHBrCH3
- 1-Bromo-3-methylbutane (1°) — CH3CH(CH3)CH2CH2Br
- 1-Bromo-2,2-dimethylpropane (1°) — (CH3)3CCH2Br
The eight structural isomers of C5H11Br are 1-bromopentane (1°), 2-bromopentane (2°), 3-bromopentane (2°), 1-bromo-2-methylbutane (1°), 2-bromo-2-methylbutane (3°), 2-bromo-3-methylbutane (2°), 1-bromo-3-methylbutane (1°), and 1-bromo-2,2-dimethylpropane (1°).
The three carbon skeletons of C5H12 (pentane, 2-methylbutane, 2,2-dimethylpropane) give eight distinct positions for Br, hence eight structural isomers of C5H11Br: three from pentane, four from 2-methylbutane, one from neopentane.
Place Br on each chemically distinct carbon of each C5 skeleton and classify by the carbon bearing Br.
Pentane skeleton - CH3CH2CH2CH2CH3
- 1-bromopentane, CH3CH2CH2CH2CH2Br - primary
- 2-bromopentane, CH3CH2CH2CHBrCH3 - secondary
- 3-bromopentane, CH3CH2CHBrCH2CH3 - secondary
2-methylbutane skeleton - (CH3)2CHCH2CH3
- 1-bromo-2-methylbutane, BrCH2CH(CH3)CH2CH3 - primary
- 2-bromo-2-methylbutane, CH3CBr(CH3)CH2CH3 - tertiary
- 2-bromo-3-methylbutane, CH3CHBrCH(CH3)CH3 - secondary
- 1-bromo-3-methylbutane, (CH3)2CHCH2CH2Br - primary
2,2-dimethylpropane (neopentane) skeleton - C(CH3)4
- 1-bromo-2,2-dimethylpropane, (CH3)3CCH2Br - primary
The eight structural isomers are: 1-bromopentane (1∘), 2-bromopentane (2∘), 3-bromopentane (2∘), 1-bromo-2-methylbutane (1∘), 2-bromo-2-methylbutane (3∘), 2-bromo-3-methylbutane (2∘), 1-bromo-3-methylbutane (1∘), and 1-bromo-2,2-dimethylpropane (1∘).
Structural Isomerism — C5H11Br
Method: Carbon Skeleton + Functional Group Position Isomerism
This method systematically builds all possible carbon skeletons (straight and branched chains) and then places the bromine atom at every unique carbon position.
Step 1 — Draw all carbon skeletons for 5 carbons
There are three distinct skeletons:
-
Straight chain (n-pentane):
C−C−C−C−C
-
One methyl branch (isopentane / 2-methylbutane):
C−C−C−C with a CH3 on carbon-2
(or equivalently on carbon-3 — same skeleton)
-
Two methyl branches (neopentane / 2,2-dimethylpropane):
C−C−C with two CH3 groups on the central carbon
Step 2 — Place Br at each unique carbon in each skeleton
Count only chemically distinct positions (symmetry reduces the count).
Skeleton 1: Straight chain (n-pentane)
- Br at C1 → 1-bromopentane (primary)
- Br at C2 → 2-bromopentane (secondary)
- Br at C3 → 3-bromopentane (secondary) (C4 and C5 are same as C2 and C1 by symmetry)
3 isomers from this skeleton.
Skeleton 2: 2-methylbutane
Number the chain so the branch gets the lowest number:
C1 - C2 - C3 - C4
|
CH3
- Br at C1 → 1-bromo-2-methylbutane (primary)
- Br at C2 → 2-bromo-2-methylbutane (tertiary)
- Br at C3 → 2-bromo-3-methylbutane (secondary) (Note: numbering gives C3 as the carbon next to branch)
- Br at C4 → 1-bromo-3-methylbutane (primary) (the branch methyl on C2 is a distinct primary carbon from C4, so these are different)
The branch methyl (on C2) is not equivalent to C4, so we get 4 isomers from this skeleton.
Skeleton 3: 2,2-dimethylpropane (neopentane)
CH3
|
CH3 - C - CH3
|
CH3
All four methyl groups are equivalent. Only one unique Br position:
- Br on any methyl → 1-bromo-2,2-dimethylpropane (primary)
1 isomer from this skeleton.
Step 3 — Total count and classification
| Skeleton | Isomers | Total |
|---|---|---|
| n-pentane | 3 | 3 |
| 2-methylbutane | 4 | 7 |
| 2,2-dimethylpropane | 1 | 8 |
All eight structural isomers are now accounted for.
Final Answer — The 8 Isomers
| IUPAC Name | Structure (condensed) | Classification |
|---|---|---|
| 1-bromopentane | CH3CH2CH2CH2CH2Br | Primary |
| 2-bromopentane | CH3CH2CH2CHBrCH3 | Secondary |
| 3-bromopentane | CH3CH2CHBrCH2CH3 | Secondary |
| 1-bromo-2-methylbutane | CH3CH2CH(CH3)CH2Br | Primary |
| 2-bromo-2-methylbutane | CH3CH2CBr(CH3)2 | Tertiary |
| 2-bromo-3-methylbutane | CH3CHBrCH(CH3)2 | Secondary |
| 1-bromo-3-methylbutane | BrCH2CH2CH(CH3)2 | Primary |
| 1-bromo-2,2-dimethylpropane | (CH3)3CCH2Br | Primary |
Key exam tip: Always check for symmetry — it reduces the number of distinct isomers. The tertiary bromide is only 2-bromo-2-methylbutane.
Here are the most common mistakes students make when tackling this exact problem, along with the conceptual fixes to avoid them.
1. Mistake: Forgetting the Carbon Skeleton First
Students often try to place the Br atom directly onto a random chain without systematically drawing all unique carbon skeletons for C5H12 (pentane).
- The Error: You end up with duplicate structures or miss an isomer entirely because you didn't realize the carbon backbone itself can be straight, branched at carbon 2, or branched at carbon 3.
- How to Avoid: Always start by drawing the three unique carbon skeletons for C5:
- n-Pentane:
C-C-C-C-C - Isopentane (2-methylbutane):
C-C(C)-C-C - Neopentane (2,2-dimethylpropane):
C-C(C)(C)-C
- n-Pentane:
- Key Insight: The Br atom is just a substituent. The shape of the carbon chain is the foundation. If you miss a skeleton, you miss a whole family of isomers.
2. Mistake: Counting Symmetry Incorrectly (The #1 Trap)
This is the most frequent error. Students place Br on every carbon they see, forgetting that symmetry makes some positions identical.
- The Error: For n-pentane, you might draw Br on carbon 1, 2, 3, 4, and 5 — that's 5 structures. But carbon 1 and carbon 5 are identical (both are terminal, primary carbons). Similarly, carbon 2 and carbon 4 are identical.
- How to Avoid: For each skeleton, label the carbons and ask: "If I flip the molecule over, does this carbon become the same as another?" Only draw Br on unique positions.
- n-Pentane: Only 3 unique positions: C1 (1-bromopentane), C2 (2-bromopentane), C3 (3-bromopentane).
- Isopentane: The terminal carbons on the main chain are not all identical. The two methyl groups on the branch are identical to each other, but different from the main chain end.
- Neopentane: All four methyl groups are identical. There is only one unique position for Br.
3. Mistake: Misclassifying Primary, Secondary, or Tertiary Bromide
Students often classify based on the number of carbons in the molecule or the position of the Br in the name, rather than the carbon atom bonded to Br.
- The Error: Calling 1-bromopentane a "secondary" bromide because it's on a chain of 5 carbons, or calling 2-bromo-2-methylbutane a "primary" bromide because it has a methyl group.
- How to Avoid: The classification depends only on the carbon directly attached to the Br atom.
- Primary (1°): The C with Br is attached to 1 other carbon (and 2 H's). Example: 1-bromopentane.
- Secondary (2°): The C with Br is attached to 2 other carbons (and 1 H). Example: 2-bromopentane.
- Tertiary (3°): The C with Br is attached to 3 other carbons (and 0 H's). Example: 2-bromo-2-methylbutane.
4. Mistake: Incorrect IUPAC Naming (Numbering the Chain Wrong)
Students often start numbering from the wrong end, leading to a higher locant number for the Br or the branch.
- The Error: Naming
Br-CH2-CH(CH3)-CH2-CH3as "2-bromo-3-methylbutane" instead of the correct "1-bromo-3-methylbutane". - How to Avoid: The IUPAC rule is: Number the parent chain so that the substituents (Br and alkyl groups) get the lowest possible set of locants. Compare the first point of difference.
- For the skeleton
C-C(C)-C-Cwith Br on the end: If you number from the Br end, you get 1-bromo-3-methylbutane. If you number from the other end, you get 4-bromo-2-methylbutane. The first set (1,3) is lower than (2,4), so the correct name is 1-bromo-3-methylbutane.
- For the skeleton
5. Mistake: Forgetting the "2,2-Dimethyl" Isomer
Students often stop after drawing the 7 isomers from n-pentane and isopentane, forgetting the neopentane skeleton entirely.
- The Error: You list only 7 isomers, missing the one from the most branched skeleton.
- How to Avoid: Remember the three skeletons. Neopentane (2,2-dimethylpropane) has only one unique carbon (the central quaternary carbon is not possible for Br, and all four methyls are identical). The only isomer here is 1-bromo-2,2-dimethylpropane (a primary bromide).
Quick Summary Checklist for This Problem
| Step | Common Mistake | How to Avoid |
|---|---|---|
| Skeletons | Drawing only 1 or 2 skeletons | Always draw all 3: straight, 2-methyl, 2,2-dimethyl. |
| Symmetry | Counting duplicate positions | Label carbons and check for mirror images. |
| Classification | Classifying by chain length | Look only at the C directly bonded to Br. |
| IUPAC Name | Wrong numbering direction | Number to give the lowest locant set to Br and branches. |
| Completeness | Missing the 8th isomer | Check the neopentane skeleton last. |
Final Answer (for reference): The 8 isomers are:
- 1-Bromopentane (1°)
- 2-Bromopentane (2°)
- 3-Bromopentane (2°)
- 1-Bromo-2-methylbutane (1°)
- 2-Bromo-2-methylbutane (3°)
- 2-Bromo-3-methylbutane (2°)
- 1-Bromo-3-methylbutane (1°)
- 1-Bromo-2,2-dimethylpropane (1°)
Showing the 12 most recent of 17 on this concept.
- CBSE 2026Set DZ1 markMCQQ.Which of the following is an aldehyde?(a) CH3−C∣∣O−H(b) CH3−CH2−C∣∣O−CH3(c) CH3−CH2−C∣∣O−CH2−CH3(d) CH3−C∣∣O−CH3
›Reveal solutionSolution
An aldehyde has the −CHO group (a carbonyl carbon bonded to at least one H). Only option (a) has this; the rest are ketones.
The functional-group test: in an aldehyde the carbonyl carbon (>C=O) carries at least one hydrogen (R−CHO). In a ketone the carbonyl carbon is bonded to two carbon atoms (R−CO−R′).
-
(a) CH3−CHO → carbonyl C bonded to one H → aldehyde (ethanal) ✓
-
(b) CH3CH2−CO−CH3 → butan-2-one → ketone
-
(c) CH3CH2−CO−CH2CH3 → pentan-3-one → ketone
-
(d) CH3−CO−CH3 → propanone (acetone) → ketone
✓Final answer(a) CH3CHO (acetaldehyde/ethanal).
-
- CBSE 2026Set A1 markMCQQ.Which of the following is Isopropyl amine ?(a) CH3-CH2-CH2-NH2(b) CH3-NH-C2H5(c) CH3-CH(NH2)-CH3(d) CH3-CH(CH3)-CH2-NH2
›Reveal solutionSolution
Isopropyl amine = propan-2-amine, CH3-CH(NH2)-CH3.
The isopropyl group is (CH3)2CH-, so isopropylamine has the amino group attached to the central carbon of a propane chain: CH3-CH(NH2)-CH3 (propan-2-amine). For reference:
-
(a) CH3-CH2-CH2-NH2 is n-propylamine (propan-1-amine)
-
(b) CH3-NH-C2H5 is N-methylethylamine (a secondary amine)
-
(d) is isobutylamine
✓Final answer(c) CH3-CH(NH2)-CH3.
-
- CBSE 2026Set ANNUAL1 markQ.How many structural isomers of C5H11Br are possible?
›Reveal solutionSolution
C5H11Br has 8 possible structural isomers, arising from bromine substitution at different positions on the three possible pentane carbon skeletons.
C5H11Br is derived from pentane (C5H12) by replacing one H with Br. Pentane itself has 3 carbon-skeleton isomers, and Br can go on different, non-equivalent carbon positions of each:
From n-pentane skeleton (CH3CH2CH2CH2CH3):
- 1-bromopentane
- 2-bromopentane
- 3-bromopentane (C4 and C5 positions are equivalent to C2 and C1 by the molecule's symmetry)
From isopentane / 2-methylbutane skeleton ((CH3)2CHCH2CH3):
4. 1-bromo-2-methylbutane
5. 2-bromo-2-methylbutane
6. 3-bromo-2-methylbutane
7. 1-bromo-3-methylbutane (isoamyl bromide)
From neopentane / 2,2-dimethylpropane skeleton ((CH3)3CCH3, i.e. (CH3)4C):
8. Neopentyl bromide (1-bromo-2,2-dimethylpropane)
Of these 8: 4 are primary bromides, 3 are secondary, and 1 is tertiary.
✓Final answer8 structural isomers.
- CBSE 2026Set ANNUAL1 markMCQQ.Ethylidine dichloride is a:(a) vic-dihalide(b) gem-dihalide(c) allylic dihalide(d) vinylic halide
›Reveal solutionSolution
Ethylidene dichloride, CH₃CHCl₂, has both chlorine atoms on the same carbon — a gem-dihalide.
Ethylidene dichloride has the structure CH₃–CHCl₂. Both chlorine atoms are attached to the same carbon atom (the second carbon). Dihalides in which both halogens sit on one carbon are called geminal (gem) dihalides; when they are on adjacent carbons they are called vicinal (vic) dihalides. Since both Cl atoms here are on one carbon, this is a gem-dihalide.
✓Final answer(b) gem-dihalide.
- CBSE 2026Set ANNUAL1 markMCQQ.The correct IUPAC name of the organic compound CH₃—CH(C₂H₅)—CH₂Br is-(a)(i) 1-Bromo-2-ethyl-2 methyl ethane(b)(ii) 1-Bromo-2-ethyl propane(c)(iii) 1-Bromo-2-methyl butane(d)(iv) 2-Methyl-1-bromo butane
›Reveal solutionSolution
CH3–CH(C2H5)–CH2Br names as 1-bromo-2-methylbutane. Correct option: (iii).
Concept. IUPAC naming of a haloalkane: (1) pick the longest carbon chain that contains the carbon bearing the halogen; (2) number so the substituents get the lowest set of locants; (3) cite substituents alphabetically as prefixes.
Steps.
- The structure is BrCH2–CH(CH3)–CH2–CH3.
- Longest chain through the C–Br carbon = 4 carbons (butane): C1(CH2Br)−C2(CH)−C3(CH2)−C4(CH3).
- Number from the Br end: bromo at C-1, methyl branch at C-2.
- Name: 1-bromo-2-methylbutane.
Why other options are wrong. (i) and (ii) use "ethane/propane" as the parent — they fail to select the longest chain (butane). (iv) "2-methyl-1-bromobutane" mis-orders the substituents (alphabetical order requires bromo before methyl).
✓Final answer(iii) 1-Bromo-2-methylbutane. This IUPAC nomenclature is common to the NCERT/CBSE-aligned UBSE Class-12 Chemistry course.
- CBSE 2025Set JZ1 markMCQQ.The correct IUPAC name for CH2=CHCH2NHCH3 is :(a) Allylmethylamine(b) 1-amine-4-pentene(c) 4-aminopent-1-ene(d) N-methylprop-2-ene-1-amine
›Reveal solutionSolution
Naming CH2=CHCH2NHCH3 as a substituted amine gives N-methylprop-2-en-1-amine — option (d).
Concept. For a secondary amine, choose the longest carbon chain attached to nitrogen as the parent amine; the smaller alkyl group on N is named as an N-substituent.
Working:
- Parent chain: CH2=CH−CH2− is a 3-carbon chain with a double bond → prop-2-ene; the amino group is on C-1 → prop-2-en-1-amine.
- The nitrogen also carries a −CH3, written as the prefix N-methyl.
Combining: N-methylprop-2-en-1-amine (the common name is allylmethylamine, but the IUPAC name is required).
✓Final answer(d) N-methylprop-2-ene-1-amine.
- CBSE 2025Set D1 markMCQQ.The number of isomeric alcohols of molecular formula C4H10O is(a) 2(b) 4(c) 7(d) 8
›Reveal solutionSolution
The four alcohols of formula C4H10O are 1-butanol, 2-methyl-1-propanol, 2-butanol and 2-methyl-2-propanol.
For the molecular formula C4H10O with an -OH group, the possible alcohols are:
- n-Butanol (butan-1-ol): CH3CH2CH2CH2OH (1°)
- Isobutyl alcohol (2-methylpropan-1-ol): (CH3)2CHCH2OH (1°)
- sec-Butyl alcohol (butan-2-ol): CH3CH2CH(OH)CH3 (2°)
- tert-Butyl alcohol (2-methylpropan-2-ol): (CH3)3COH (3°)
That gives 4 isomeric alcohols. (The remaining C4H10O isomers such as diethyl ether are ethers, not alcohols.)
✓Final answer(B) 4 isomeric alcohols of formula C4H10O.
- CBSE 2025Set ANNUAL1 markMCQQ.The number of isomers in C2BrClFI is(a) 3(b) 4(c) 5(d) 6
›Reveal solutionSolution
C2BrClFI, an ethylene bearing all four halogens (Br, Cl, F, I) with no hydrogens, has 6 possible isomers.
Since the formula has 2 carbons and exactly 4 substituents (Br, Cl, F, I) with no hydrogens, this corresponds to a fully-substituted ethylene, i.e. an alkene of type (X)(Y)C=C(Z)(W), where each carbon bears 2 of the 4 different halogens.
Step 1 — constitutional (positional) isomers: choose which 2 of the 4 halogens sit on one carbon (the other 2 automatically go on the other carbon). The number of distinct ways to split 4 different halogens into two unordered pairs is 3: {Br,Cl}|{F,I}, {Br,F}|{Cl,I}, {Br,I}|{Cl,F}.
Step 2 — geometric (cis/trans) isomers: for each of these 3 constitutional arrangements, since each carbon carries 2 different substituents, the molecule can exist as 2 geometric isomers (cis and trans, i.e. Z and E).
Total isomers = 3 (constitutional arrangements) x 2 (geometric isomers each) = 6.
✓Final answer(D) 6.
- CBSE 2024Set ANNUAL1 markMCQQ.An isomer of ethanol is(a) Methanol(b) Dimethyl ether(c) Diethyl ether(d) Ethylene glycol
›Reveal solutionSolution
Dimethyl ether (CH3–O–CH3) is the classic functional isomer of ethanol (C2H6O).
Ethanol (CH3CH2OH) has molecular formula C2H6O. Dimethyl ether (CH3–O–CH3) has the identical molecular formula C2H6O but a completely different functional group (ether linkage instead of an –OH group) — this is an example of functional group isomerism. Methanol (CH4O) and diethyl ether (C4H10O) have different molecular formulas, so they are not isomers of ethanol; ethylene glycol (C2H6O2) also has a different formula.
✓Final answer(B) Dimethyl ether.
- CBSE 2024Set ANNUAL1 markMCQQ.The total number of isomers for the compounds having molecular formula C4H10O is(a) 7(b) 6(c) 3(d) 4
›Reveal solutionSolution
C4H10O has 7 total structural isomers: 4 alcohols + 3 ethers.
Alcohols (C4H9OH, 4 isomers): butan-1-ol, butan-2-ol, 2-methylpropan-1-ol (isobutanol), 2-methylpropan-2-ol (tert-butanol).
Ethers (C4H10O, 3 isomers): diethyl ether (C2H5–O–C2H5), methyl n-propyl ether (CH3–O–CH2CH2CH3), methyl isopropyl ether (CH3–O–CH(CH3)2).
Total = 4 + 3 = 7 constitutional isomers.
✓Final answer(A) 7.
- CBSE 2023Set ANNUAL1 markQ.How many isomeric monochloro derivatives will be formed when 2-methylpropane is subjected to photochlorination ?
›Reveal solutionSolution
2-Methylpropane has only two chemically distinct kinds of hydrogen (9 equivalent primary H's and 1 tertiary H), so free-radical photochlorination gives exactly two monochloro isomers.
2-Methylpropane (isobutane), (CH3)3CH, has two types of hydrogen atoms:
- 9 primary hydrogens (three equivalent CH3 groups), all chemically equivalent by symmetry — substitution at any of these gives the same product: 1-chloro-2-methylpropane, (CH3)2CHCH2Cl.
- 1 tertiary hydrogen (on the central carbon) — substitution here gives: 2-chloro-2-methylpropane (tert-butyl chloride), (CH3)3CCl.
Since photochlorination is a free-radical substitution that can occur at any C–H bond, but chemically equivalent hydrogens always give the identical product, the number of distinct isomeric monochloro products depends only on the number of structurally different types of hydrogen, not the total count of hydrogens.
✓Final answer2 isomeric monochloro derivatives: 1-chloro-2-methylpropane (from the primary H's) and 2-chloro-2-methylpropane / tert-butyl chloride (from the tertiary H).
- CBSE 2023Set ANNUAL1 markMCQQ.CH2=CH-CH2-CH3 and CH3-CH=CH-CH3 are:(a) Chain isomers(b) Position isomers(c) Functional isomers(d) Metamers
›Reveal solutionSolution
CH2=CH-CH2-CH3 (1-butene) and CH3-CH=CH-CH3 (2-butene) share the same carbon skeleton and functional group but differ only in where the double bond sits — that is positional isomerism.
Both molecules have molecular formula C4H8 and the same unbranched 4-carbon chain, and both are alkenes (same functional group, so not functional isomers; same chain, so not chain isomers).
The only difference is the location of the C=C double bond: between C1–C2 in the first compound (1-butene) versus between C2–C3 in the second (2-butene). This difference in position of the double bond (or functional group) along an otherwise identical skeleton defines position isomers.
✓Final answerPosition isomers (option b).
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