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Basics of Organic Chemistry question

2002 · Shift 0 · Q12
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Basics of Organic Chemistry question

2002 · Shift 0 · Q12

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Which of the following does not show geometrical isomerism?
  1. A
    1,2-dichloro-1-pentene
  2. B
    1,3-dichloro-2-pentene
  3. C
    1,1-dichloro-1-pentene
  4. D
    1,4-dichloro-2-pentene
View written solutionFree

Correct answer: C

  1. Condition for geometrical isomerism

Geometrical isomerism about a double bond is possible only when each carbon of the C=CC=CC=C bond has two different substituents.

If any one of the double-bonded carbons has two identical groups, then geometrical isomerism is not possible.


  1. Check each option

Option A: 1,21,21,2-dichloro-111-pentene

Structure: CHCl=C(Cl)−CH2−CH2−CH3\mathrm{CHCl=C(Cl)-CH_2-CH_2-CH_3}CHCl=C(Cl)−CH2​−CH2​−CH3​

  • Carbon-1 of double bond has: H\mathrm{H}H and Cl\mathrm{Cl}Cl
  • Carbon-2 of double bond has: Cl\mathrm{Cl}Cl and C3H7\mathrm{C_3H_7}C3​H7​

Both double-bonded carbons have two different groups.

⇒\Rightarrow⇒ Shows geometrical isomerism.


Option B: 1,31,31,3-dichloro-222-pentene

Structure: CH2Cl−CH=C(Cl)−CH2−CH3\mathrm{CH_2Cl-CH=C(Cl)-CH_2-CH_3}CH2​Cl−CH=C(Cl)−CH2​−CH3​

  • Carbon-2 of double bond has: H\mathrm{H}H and CH2Cl\mathrm{CH_2Cl}CH2​Cl
  • Carbon-3 of double bond has: Cl\mathrm{Cl}Cl and C2H5\mathrm{C_2H_5}C2​H5​

Again, both carbons have two different substituents.

⇒\Rightarrow⇒ Shows geometrical isomerism.


Option C: 1,11,11,1-dichloro-111-pentene

Structure: CCl2=CH−CH2−CH2−CH3\mathrm{CCl_2=CH-CH_2-CH_2-CH_3}CCl2​=CH−CH2​−CH2​−CH3​

  • Carbon-1 of double bond has: Cl\mathrm{Cl}Cl and Cl\mathrm{Cl}Cl
  • Carbon-2 of double bond has: H\mathrm{H}H and C3H7\mathrm{C_3H_7}C3​H7​

Here, one double-bond carbon has two identical substituents (Cl\mathrm{Cl}Cl and Cl\mathrm{Cl}Cl).

⇒\Rightarrow⇒ Does not show geometrical isomerism.


Option D: 1,41,41,4-dichloro-222-pentene

Structure: CH2Cl−CH=CH−CHCl−CH3\mathrm{CH_2Cl-CH=CH-CHCl-CH_3}CH2​Cl−CH=CH−CHCl−CH3​

  • Carbon-2 of double bond has: H\mathrm{H}H and CH2Cl\mathrm{CH_2Cl}CH2​Cl
  • Carbon-3 of double bond has: H\mathrm{H}H and CHClCH3\mathrm{CHClCH_3}CHClCH3​

Both double-bonded carbons have two different groups.

⇒\Rightarrow⇒ Shows geometrical isomerism.


  1. Conclusion

The compound that does not show geometrical isomerism is: C: 1,1-dichloro-1-pentene\boxed{\text{C: }1,1\text{-dichloro-}1\text{-pentene}}C: 1,1-dichloro-1-pentene​


  1. Comparison with stored correct answer

Stored correct answer: C

Derived answer: C

They match.

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