Q.Draw all the isomers (geometrical and optical) of:
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🔒 Start your 14-day free trial to unlock the full solution →Concept understanding — Geometrical Isomerism Conditions
Geometrical Isomerism: The Intuition
Imagine you have two friends standing on opposite sides of a door. If the door is open, they can walk around and swap places easily — there's no real difference between who is on the left and who is on the right. But if the door is locked shut, they are stuck. One is permanently on the left side, the other on the right. That locked door creates two distinct arrangements: Friend A on the left, Friend B on the right versus Friend A on the right, Friend B on the left.
That locked door is the key idea behind geometrical isomerism.
In chemistry, molecules are three-dimensional. Atoms connected by a single bond can rotate freely — like an open door. But a double bond (or a ring structure) locks the atoms in place. If you have two different groups attached to each carbon of a double bond, you get two distinct spatial arrangements that cannot interconvert without breaking the bond. These are geometrical isomers (also called cis-trans or E-Z isomers).
The Precise Conditions
For a molecule to show geometrical isomerism, it must satisfy two conditions simultaneously:
Condition 1: There must be a restricted rotation around a bond — typically a carbon-carbon double bond (C=C) or a ring structure.
Condition 2: Each of the two atoms (or groups) involved in that restricted rotation must have two different substituents attached to it.
Let's unpack each.
Condition 1: Restricted Rotation
A single bond (C−C) allows free rotation — the atoms spin around the bond axis like a wheel. So no geometrical isomers exist there. A double bond (C=C) has a pi (π) bond that locks the molecule flat. Rotation would break the π bond, which requires a lot of energy (about 250–270 kJ/mol). At room temperature, this rotation simply does not happen.
Rings (like cyclopropane, cyclobutane, etc.) also restrict rotation because the ring is a closed loop — atoms cannot rotate past each other without breaking the ring.
Condition 2: Two Different Substituents on Each End
This is the "different groups" rule. Look at each carbon of the double bond (or each ring carbon involved). If both carbons have two different groups attached, geometrical isomers exist. If even one carbon has two identical groups, there is only one possible arrangement.
A common mistake: students check only one carbon. Both carbons must have two different substituents. If one carbon has two identical groups (like two hydrogens), the molecule is identical in both arrangements — no isomerism.
How to Check: A Step-by-Step Method
Take any molecule with a double bond. Follow these steps:
- Identify the double bond (or ring). Mark the two carbon atoms involved.
- List the two groups attached to the first carbon. Are they different from each other? If yes, proceed. If no → no geometrical isomerism.
- List the two groups attached to the second carbon. Are they different from each other? If yes → geometrical isomerism exists. If no → no geometrical isomerism.
If the two groups on a carbon are identical, the molecule is symmetric about that carbon. Flipping the other side gives the same molecule — no isomers.
Examples to Cement the Idea
Example 1: But-2-ene (CH3CH=CHCH3)
- Carbon 1 of the double bond: attached to CH3 and H → different ✓
- Carbon 2 of the double bond: attached to CH3 and H → different ✓
Result: Two geometrical isomers exist — cis (both methyl groups on the same side) and trans (methyl groups on opposite sides).
Example 2: 1,2-Dichloroethene (ClCH=CHCl)
- Carbon 1: attached to Cl and H → different ✓
- Carbon 2: attached to Cl and H → different ✓
Result: cis and trans isomers exist.
Example 3: 1,1-Dichloroethene (Cl2C=CH2)
- Carbon 1: attached to Cl and Cl → identical ✗ …
Why this formula?
Geometrical Isomerism: Why the Conditions Hold
Geometrical isomerism (also called cis-trans or E-Z isomerism) arises when atoms or groups are arranged differently in space around a rigid part of a molecule — typically a double bond or a ring. The key is that rotation is restricted, so the spatial positions become fixed and distinct.
Let’s break down why the conditions are what they are.
1. The Core Requirement: Restricted Rotation
For two molecules to be geometrical isomers, they must have the same connectivity but different spatial arrangement due to a barrier to rotation.
- Double bonds (C=C): The π-bond locks the two carbons in place — rotation requires breaking the π-bond (energy ~250 kJ/mol), so it doesn’t happen at room temperature.
- Rings (e.g., cycloalkanes): The ring structure physically prevents free rotation about C–C single bonds within the ring.
Why this matters: Without restricted rotation, the molecule would freely interconvert between arrangements — no distinct isomers exist.
2. Condition 1: Two Different Groups on Each Carbon (for C=C)
Consider a general alkene:
C=C
Each carbon must have two different substituents (not counting the other carbon of the double bond).
Why?
- If one carbon has two identical groups (e.g., both H), then swapping the groups on that carbon produces the same molecule — no isomerism.
Example:
- 1,2-dichloroethene (ClHC=CHCl): Each carbon has H and Cl (different) → geometrical isomers exist.
- 1,1-dichloroethene (Cl2C=CH2): One carbon has two Cl (identical) → no geometrical isomers.
Formal condition:
For a C=C bond, geometrical isomerism is possible iff each doubly bonded carbon bears two different substituents.
3. Condition 2: For Rings — Similar Logic
In a ring (e.g., cyclopropane, cyclohexane), the ring itself restricts rotation. Here, geometrical isomerism occurs when two substituents on different ring carbons can be on the same side (cis) or opposite sides (trans).
Why?
- The ring is a closed loop — you cannot rotate one carbon relative to another without breaking bonds.
- If the two substituents are on different carbons, their relative orientation (same side / opposite sides) is fixed.
Condition:
- The ring must have at least two substituents (could be same or different) on different carbons.
- If both substituents are on the same carbon, swapping them doesn’t change the molecule (no isomerism).
Example:
- 1,2-dimethylcyclopropane: Two methyl groups on adjacent carbons → cis and trans isomers exist.
- 1,1-dimethylcyclopropane: Both methyls on same carbon → no geometrical isomerism.
4. The E-Z Notation (Why It’s Needed)
When the four substituents on a C=C are all different, cis-trans naming fails. The Cahn-Ingold-Prelog priority rules assign E (opposite sides) or Z (same side).
Why this works:
- Priority is based on atomic number (higher = higher priority). …
Concept: Geometrical Isomerism in octahedral complexes with bidentate ligands (en = ethylenediamine). Optical activity arises when the complex lacks a plane of symmetry.
(i) [CoCl2(en)2]+
- Two Cl ligands can be cis (90°) or trans (180°).
- cis form has no plane of symmetry → exists as a pair of non-superimposable mirror images (optical isomers). …
All three are octahedral Co(III) complexes; the bidentate en must occupy two cis sites. (i) [CoCl2(en)2]+ -> 3 isomers: trans (optically inactive) + cis (optically active d/l pair).
(ii) [Co(NH3)Cl(en)2]2+ -> 3 isomers: trans (inactive) + cis (active d/l pair).
(iii) [Co(NH3)2Cl2(en)]+ -> 4 isomers: three geometrical forms, of which the cis-NH3/cis-Cl form is optically active (d/l).
(i) [CoCl2(en)2]+
Co(III), octahedral; two en chelates and two Cl−.
- trans: the two Cl− are 180∘ apart and the two en lie in the equatorial plane. A plane of symmetry is present -> optically inactive.
- cis: the two Cl− are 90∘ apart. The ion has no plane of symmetry -> optically active, existing as a non-superimposable d/l enantiomeric pair.
Total = 3 isomers (1 trans + cis d and l).
(ii) [Co(NH3)Cl(en)2]2+
Type [M(en)2bc] with b=NH3, c=Cl.
- trans (NH3 and Cl axial, 180∘): a plane of symmetry is present -> optically inactive.
- cis (NH3 and Cl at 90∘): no plane of symmetry -> optically active, a d/l pair.
Total = 3 isomers (1 trans + cis d and l).
(iii) [Co(NH3)2Cl2(en)]+
Type [M(en)a2b2] with a=NH3, b=Cl. en takes two cis sites; the remaining four sites hold two NH3 and two Cl. Only one trans pair of sites is available, so exactly three geometrical arrangements exist: …
Method: Coordination Isomer Enumeration via Coordination Sphere Analysis
We use the Coordination Geometry + Ligand Arrangement method for octahedral complexes. The steps:
- Identify coordination number → 6 (octahedral) for all.
- List all ligands and their denticity (monodentate vs bidentate).
- Determine possible geometric arrangements for bidentate ligands (en = ethylenediamine, bidentate).
- Check for optical activity — look for absence of plane of symmetry / centre of inversion.
- Draw all distinct isomers — geometric first, then optical.
(i) [CoCl2(en)2]+
Step 1: Co(III), coordination number 6. Ligands: 2 × Cl⁻ (monodentate), 2 × en (bidentate).
Step 2: The two en ligands can occupy positions relative to each other:
- cis — both en rings adjacent (90° apart)
- trans — both en rings opposite (180° apart)
Step 3: Check optical activity:
- cis isomer: No plane of symmetry → optically active (exists as a pair of enantiomers)
- trans isomer: Has a plane of symmetry → optically inactive
Isomers:
- Geometrical: cis and trans
- Optical: cis has two enantiomers (d and l); trans has none
Total isomers: 3 (cis-d, cis-l, trans)
(ii) [Co(NH3)Cl(en)2]2+
Step 1: Ligands: 1 × NH₃, 1 × Cl⁻ (both monodentate), 2 × en (bidentate).
Step 2: The two en ligands are bidentate, so (as in part (i)) they can only occupy cis positions relative to each other — a chelate ring cannot span trans sites. This leaves two remaining coordination positions for NH₃ and Cl⁻, and these two remaining positions can themselves be cis or trans to each other.
Step 3: So there are exactly two geometrical arrangements:
- cis: NH₃ and Cl⁻ occupy adjacent (cis) positions → 1 geometrical isomer
- trans: NH₃ and Cl⁻ occupy opposite (trans) positions → 1 geometrical isomer
Step 4: Check optical activity:
- cis (NH₃/Cl cis): No plane of symmetry → optically active (2 enantiomers)
- trans (NH₃/Cl trans): Has a plane of symmetry → optically inactive
Total isomers: 3 (cis: d and l; trans: 1)
(iii) [Co(NH3)2Cl2(en)]+
Step 1: Ligands: 2 × NH₃, 2 × Cl⁻ (monodentate), 1 × en (bidentate).
Step 2: The en ligand is fixed in one position. The four monodentate ligands occupy the remaining four positions.
Step 3: Possible arrangements of the two NH₃ and two Cl: with en chelating two adjacent sites, only one trans axis survives among the four remaining positions — so the two NH₃ and the two Cl can never BOTH be trans at the same time. The distinct arrangements are: …
🧠 Core Concept Recap (Why This Matters)
Geometrical isomerism in coordination compounds arises when ligands can occupy different positions around the metal ion. Optical isomerism occurs when the complex is non-superimposable on its mirror image (chiral).
Key conditions for geometrical isomerism:
- Coordination number 4 or 6 (most common)
- Presence of at least two different types of ligands (or ambidentate ligands)
- Ma₂b₂, Ma₂bc, M(AA)₂, M(AA)bc type complexes (where AA = bidentate ligand)
✗ Common Mistake #1: Forgetting that en is a bidentate ligand
What students do wrong:
They treat en (ethylenediamine) as two separate monodentate ligands. This leads to wrong isomer counts and wrong geometries.
Example: In [CoCl₂(en)₂]⁺, some students draw en as two separate NH₂CH₂CH₂NH₂ groups — but it’s one chelating ligand that occupies two adjacent positions.
How to avoid:
- Always remember:
enis bidentate — it occupies two coordination sites but acts as one ligand unit. - In drawings, show
enas a curved line connecting two coordination positions.
✗ Common Mistake #2: Confusing cis and trans for bidentate ligands
What students do wrong:
For [CoCl₂(en)₂]⁺, they think en can be placed trans to each other — but bidentate ligands cannot span trans positions (too far apart).
How to avoid:
- A single bidentate ligand can never span two trans positions — each
enmust chelate two adjacent (cis) sites; the chelate ring is too short to reach across the octahedron. - The cis/trans labels of
[CoCl₂(en)₂]⁺therefore refer to the two Cl⁻ ligands, not to the en rings — and the cis form is optically active.
✗ Common Mistake #3: Missing optical isomerism in [CoCl₂(en)₂]⁺
What students do wrong:
They draw only cis and trans geometrical isomers, but forget that the cis isomer is chiral (non-superimposable mirror image).
How to avoid:
- Check for plane of symmetry in the cis isomer. In
[CoCl₂(en)₂]⁺, the cis form has no plane of symmetry → it exists as a pair of enantiomers (d and l). - Trans isomer has a plane of symmetry → no optical isomerism.
Correct answer for (i):
- Geometrical: cis and trans
- Optical: cis → 2 enantiomers; trans → none
✗ Common Mistake #4: Claiming [Co(NH₃)Cl(en)₂]²⁺ has only ONE arrangement because en "fixes" everything
What students do wrong:
They reason that since both en ligands must chelate cis positions, the NH₃ and Cl have no freedom left — and conclude only one geometrical isomer exists. Others try to draw a trans arrangement of a single en ligand itself.
How to avoid:
- Each
enmust chelate two adjacent sites, but the two REMAINING sites (holding NH₃ and Cl) can still be cis or trans to each other — that is exactly the cis/trans choice. - cis (NH₃ and Cl at 90°): no plane of symmetry → chiral → 2 enantiomers
- trans (NH₃ and Cl at 180°): plane of symmetry → optically inactive
Correct answer for (ii):
- Geometrical: cis and trans
- Optical: the cis form exists as a d/l pair → 3 stereoisomers in total
✗ Common Mistake #5: Overcounting or undercounting isomers for [Co(NH₃)₂Cl₂(en)]⁺
What students do wrong:
They treat en as two separate ligands and try to draw many cis/trans combinations — but en is bidentate, so it occupies two adjacent sites. Some students also wrongly assume NH₃ and Cl can BOTH be trans to each other at once.
How to avoid:
- First, fix
enas a cis unit (it must be adjacent) — this leaves only one genuine trans axis among the remaining four sites, so NH₃ and Cl can never both be trans simultaneously. - Then, place the two
NH₃and twoClin the remaining four positions. - Possible arrangements:
- Both NH₃ cis to each other and both Cl cis to each other → one isomer (chiral, gives a d/l pair) …
- GUJCET 2025Set 031 markMCQQ.If [Co(NH3)x(NO2)y] shows facial and meridional isomers, identify values of x and y. (A) x=4,y=2 (B) x=2,y=2 (C) x=2,y=4 (D) x=3,y=3
›Reveal solutionSolution
[!TLDR]
fac-mer isomerism requires an MA3B3 octahedral complex, so x=3 and y=3.
Concept
In an octahedral complex, facial-meridional (geometrical) isomerism arises specifically for the MA3B3 stoichiometry: the three identical ligands either share a common face (fac) or lie along a meridian (mer).
Solution …
- GUJCET 2025Set 031 markMCQQ.How many minimum numbers of C-atom containing monohaloalkane shows Optical Isomerism? (A) 6 (B) 4 (C) 3 (D) 5
›Reveal solutionSolution
Optical isomerism needs an asymmetric carbon (four different groups); the smallest such monohaloalkane has 4 carbons.
Concept — chirality. A carbon bonded to four different groups is a stereocentre.
Steps.
- 1, 2, 3 carbons cannot give four different groups on one carbon (e.g. 2-chloropropane's central C has two identical CH3). …
- GUJCET 2024Set 131 markMCQQ.Identify the optically active compound from the following. (A) [Pt(NH3)2Cl2] (B) [Co(NH3)6]Cl2 (C) [Co(en)3]Cl3 (D) [Co(NH3)5Cl]Cl
›Reveal solutionSolution
A tris(bidentate) octahedral complex like [Co(en)3]3+ is chiral (has Δ and Λ enantiomers), so it is optically active.
Concept: Optical activity requires the absence of any symmetry plane/centre.
- [Pt(NH3)2Cl2] (square planar) has a plane of symmetry — optically inactive.
- [Co(NH3)6]2+ and [Co(NH3)5Cl]2+ are symmetric — inactive. …
- GUJCET 2023Set 091 markMCQQ.What kind of isomerism exists between [Cr(H2O)6]Cl3 and [Cr(H2O)5Cl]Cl2⋅H2O? (A) Ionisation (B) Solvate (C) Coordination (D) Linkage
›Reveal solutionSolution
[!TLDR]
Water shifting between the coordination sphere and the lattice makes these solvate (hydrate) isomers.
Concept
Solvate (hydrate) isomerism arises when the number of solvent molecules inside the coordination sphere differs, the extra solvent instead being present as molecules of crystallisation.
Solution …
- GSEB Higher Secondary Certificate (HSC) Examination 2023Set ANNUAL1 markMCQQ.Number of possible isomers for [Cr(H2O)2(C2O4)2]^- are ___.(a) 6(b) 4(c) 2(d) 3
›Reveal solutionSolution
[M(AA)2B2] type: trans (1) + cis (optically active, 2 enantiomers) = 3 isomers.
[Cr(H2O)2(C2O4)2]^- has two bidentate oxalate ligands (AA) and two monodentate water ligands (B), i.e. type [M(AA)2B2].
- Geometric isomers: cis (the two H2O adjacent) and trans (the two H2O opposite). …
- GUJCET 2022Set 171 markMCQQ.How many numbers of Geometrical Isomers of [Pt (NH3) (Br) (Cl) (Py)] will have? (A) 3 (B) 2 (C) 1 (D) 4
›Reveal solutionSolution
Square-planar Mabcd gives exactly 3 geometrical isomers.
Concept. Pt(II) complexes are square planar. For a square-planar complex with four different monodentate ligands (Mabcd), the number of geometrical isomers equals 3 — determined by which ligand sits trans to a chosen reference ligand (the other three each in turn). …
- GSEB Higher Secondary Certificate (HSC) Examination 2022Set ANNUAL1 markMCQQ.For [PtCl2(NH3)2], which type of isomerism is (correctly) possible? (Source scan of the options is severely degraded/illegible even after re-rendering at 6x native resolution with contrast enhancement - see transcriber note.)(a) [illegible in source scan](b) [illegible in source scan](c) [illegible in source scan](d) [illegible in source scan]
›Reveal solutionSolution
The options for this MCQ could not be transcribed from the source scan even at 6x re-render, so the specific correct letter cannot be determined honestly - but the underlying chemistry is answerable.
[PtCl2(NH3)2] is a square planar complex of the type [MA2B2]. This class of complex characteristically exhibits geometrical (cis-trans) isomerism: the cis isomer has the two identical ligands (Cl) adjacent (90° apart) and the trans isomer has them opposite (180° apart). Square planar MA2B2 complexes do NOT show optical isomerism (they have a plane of symmetry in both cis and trans forms), so if the options include 'optical isomerism' that would be the incorrect choice, while 'geometrical (cis …
- GUJCET 2020Set 071 markMCQQ.Which isomerism is possible in hexa ammine cobalt (III) hexa cyanido chromate (III) complex? (A) Ionisation isomerism (B) Co-ordination isomerism (C) Linkage isomerism (D) Solvate isomerism
›Reveal solutionSolution
[Co(NH3)6][Cr(CN)6] has complex cation and complex anion ⇒ coordination isomerism. …
- GUJCET 2019Set 131 markMCQQ.Which of the following complex possess meridional isomer? (A) [Co(NH3)5Cl] (B) [Co(NH3)2Cl4] (C) [Co(NH3)4Cl2] (D) [Co(NH3)3Cl3]
›Reveal solutionSolution
Meridional (mer) and facial (fac) isomers occur only for an octahedral MA3B3 type, i.e. [Co(NH3)3Cl3].
Concept: In an octahedral MA3B3 complex the three identical ligands can occupy three positions around a meridian (mer) or three positions forming a triangular face (fac). This isomerism is unique to the A3B3 pattern.
Steps:
- [Co(NH3)5Cl] = MA5B: no such isomerism. …
- GSEB Higher Secondary Certificate (HSC) Examination 2018Set ANNUAL1 markMCQQ.Which of the following complex ions does not possess optical isomerism?(a) [Co(en)2(NH3)2]^2+(b) [Co(CO)4(en)]^3+(c) [Co(en)(H2O)4]^2+(d) [Co(H2O)3Br3]^3+
›Reveal solutionSolution
[Co(H2O)3Br3] is type MA3B3 (all monodentate); its geometric isomers are achiral, so it has no optical isomerism.
Optical isomerism in octahedral complexes needs a non-superimposable mirror image (no plane of symmetry).
- (a) [Co(en)2(NH3)2]^2+ , type M(AA)2B2: the cis form is chiral -> DOES show optical isomerism.
- (d) [Co(H2O)3Br3]^3+ , type MA3B3 with only monodentate ligands: both the facial (fac) and meridional (mer) arrangements possess a plane of symmetry and are superimposable on their mirror images -> NO optical isomerism. …
- GUJCET 2014Set A1 markMCQQ.Which of the following complex does not show optical isomerism? (A) [Cr(C2O4)3]3− (B) Cis [Pt(Br)2(en)2]2+ (C) [CrCl2(NH3)2en]+ (D) [Cr(NH3)4SO4]+
›Reveal solutionSolution
[!TLDR] [Cr(NH3)4(SO4)]+ has a symmetry plane and is achiral; the other three (tris-oxalato, cis-bis-en, and the en/2NH3/2Cl complex) can be resolved into enantiomers.
Concept
Optical isomerism requires a chiral (dissymmetric) complex — one with no plane and no centre of symmetry. Tris-chelate complexes [M(AA)3] and cis-[M(AA)2X2] / cis-[M(AA)2XY] arrangements are classic chiral octahedral species.
Solution
- (A) [Cr(C2O4)3]3−: tris(oxalato) — chiral, shows optical isomerism.
- (B) cis-[Pt(Br)2(en)2]2+: cis-bis(en) — chiral, shows optical isomerism. …
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