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Basics of Organic Chemistry question

2015 · Shift 0 · Q2
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Basics of Organic Chemistry question

2015 · Shift 0 · Q2

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Which of the following compounds will exhibit geometrical isomerism?
  1. A
    3-Phenyl-1-butene
  2. B
    2-Phenyl-1-butene
  3. C
    1,1-Diphenyl-1-propane
  4. D
    1-Phenyl-2-butene
View written solutionFree

Correct answer: D

  1. Condition for geometrical isomerism
    A compound shows geometrical (E/ZE/ZE/Z or cis-trans) isomerism about a double bond only if each carbon of the C=CC=CC=C bond has two different substituents.

  2. Check each option

Option A: 3-Phenyl-1-butene

Structure: CH2=CH−CH(Ph)−CH3\mathrm{CH_2=CH-CH(Ph)-CH_3}CH2​=CH−CH(Ph)−CH3​ For the double bond:

  • Left carbon = CH2\mathrm{CH_2}CH2​, substituents are HHH and HHH
  • Since one double-bond carbon has two identical substituents, geometrical isomerism is not possible.

Option B: 2-Phenyl-1-butene

Structure: CH2=C(Ph)−CH2−CH3\mathrm{CH_2=C(Ph)-CH_2-CH_3}CH2​=C(Ph)−CH2​−CH3​ For the double bond:

  • Left carbon = CH2\mathrm{CH_2}CH2​, substituents are HHH and HHH
  • Again, one double-bond carbon has identical substituents, so geometrical isomerism is not possible.

Option C: 1,1-Diphenyl-1-propane

Structure: (Ph)2C−CH2−CH3\mathrm{(Ph)_2C-CH_2-CH_3}(Ph)2​C−CH2​−CH3​ This is a saturated compound; there is no C=CC=CC=C double bond to restrict rotation. Hence geometrical isomerism is not possible.

Option D: 1-Phenyl-2-butene

Structure: Ph−CH2−CH=CH−CH3\mathrm{Ph-CH_2-CH=CH-CH_3}Ph−CH2​−CH=CH−CH3​ For the double bond:

  • Left double-bond carbon has substituents: HHH and CH2Ph\mathrm{CH_2Ph}CH2​Ph
  • Right double-bond carbon has substituents: HHH and CH3\mathrm{CH_3}CH3​

Each carbon of the double bond has two different groups, so geometrical isomerism is possible.

  1. Conclusion Only Option D exhibits geometrical isomerism.
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