The incorrect statements regarding geometrical isomerism are : (A) Propene shows geometrical isomerism. (B) Trans isomer has identical atoms/groups on the opposite sides of the double bond. (C) Cis-but-2-ene has higher dipole moment than trans-but-2-ene. (D) 2-methylbut-2-ene shows two geometrical isomers. (E) Trans-isomer has lower melting point that cis isomer. Choose the CORRECT answer from the options given below : (1) (A), (D) and (E) only (2) (C), (D) and (E) only (3) (B) and (C) only (4) (A) and (E) only
Detailed Explanation
Key Theory
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Requirement for Geometrical (cis–trans) Isomerism
• Each carbon of the C=C must be bonded to two different substituents.
• If either carbon carries two identical groups, no cis/trans is possible. -
Cis vs. Trans
• Cis: Identical (or priority-1) groups on the same side of the double bond.
• Trans: Identical (or priority-1) groups on opposite sides. -
Physical Property Trends
• Melting point: Trans > Cis (better crystal packing).
• Boiling point & Dipole: Cis > Trans (net dipole higher in cis).
Applying the Theory to Each Statement
Label | Molecule / Statement | Why it is Correct or Wrong |
---|---|---|
(A) | Propene has CH₃–CH=CH₂ | Terminal carbon has two H’s → no geometrical isomerism → statement wrong |
(B) | Definition of trans | Matches textbook definition → statement right |
(C) | Dipole of cis-but-2-ene higher | True, vectors add → statement right |
(D) | 2-Methylbut-2-ene gives two GI | Left C of C=C has two CH₃’s (identical) → no GI → statement wrong |
(E) | Trans melts lower than cis | Trend is opposite → statement wrong |
Hence the incorrect ones are (A), (D), (E).
Simple Explanation (ELI5)
What’s Being Asked?
Imagine you have toy cars linked by a stiff rod (the double bond). Because the rod can’t twist, the cars may be stuck facing the same direction (cis) or opposite directions (trans).
The question lists five sentences about these “stuck-together” cars and asks which sentences are wrong.
How To Check Each Sentence
- Propene: One end of the rod has two identical wheels (two H’s), so you can’t tell left from right—no cis/trans possible.
- Trans meaning: "Same pieces on opposite sides" is the right definition.
- Dipole moment: When the big pieces (CH₃) sit on the same side (cis), their little pulls add up, so the magnet‐arrow (dipole) is bigger than in trans.
- 2-Methylbut-2-ene: One end of the rod again has two identical CH₃ groups, so it can’t have cis/trans.
- Melting point: Trans shapes are straighter like sticks and pack better, so they usually melt at higher temperatures than the bent cis shapes.
Result
So the wrong ones are (A), (D), and (E).
Step-by-Step Solution
Step-by-Step Verification
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Check Propene (CH₃–CH=CH₂)
• Right-hand carbon has two H’s ⇒ only one unique group
• No geometrical isomerism ⇒ Statement (A) is wrong -
Definition of Trans
• Trans = identical groups on opposite sides ⇒ Statement (B) is correct -
Dipole in But-2-ene
• In cis-isomer, CH₃ vectors reinforce
• In trans-isomer, CH₃ vectors cancel
• ⇒ Statement (C) is correct -
2-Methylbut-2-ene (CH₃–C(CH₃)=CH–CH₃)
• Left carbon attached to CH₃ & CH₃ (identical)
• Cannot form cis/trans ⇒ Statement (D) is wrong -
Melting Points
• Trans isomers more symmetrical → better crystal packing → higher than cis
• Statement (E) says the opposite ⇒ wrong
List of Incorrect Statements
(A), (D), (E)
Final Answer
Option (1)
Examples
Example 1
Cis and trans fats: trans fats pack tightly, giving them higher melting points—hence they are solid at room temperature, unlike cis vegetable oils.
Example 2
Vision chemistry: the cis–trans isomerisation of retinal in our eyes triggers the vision signal.
Example 3
Polymer stiffness: trans-polyisoprene (gutta-percha) is hard; cis-polyisoprene (natural rubber) is elastic—the difference is just cis vs. trans at many double bonds.
Visual Representation
References
- [1]Paula Yurkanis Bruice – Organic Chemistry (chapter on stereochemistry)
- [2]Peter Sykes – A Guidebook to Mechanism in Organic Chemistry (section on cis–trans isomerism)
- [3]IIT JEE Main & Advanced – Previous Years’ Question Papers on Stereochemistry
- [4]NCERT Chemistry Class 11 – Chapter 12 Organic Chemistry: Some Basic Principles and Techniques