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Basics of Organic Chemistry question

2010 · Shift 0 · Q3
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Basics of Organic Chemistry question

2010 · Shift 0 · Q3

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Out of the following, the alkene that exhibits optical isomerism is
  1. A
    3–methyl–2–pentene
  2. B
    4–methyl–1–pentene
  3. C
    3–methyl–1–pentene
  4. D
    2–methyl–2–pentene
View written solutionFree

Correct answer: C

  1. Condition for optical isomerism
    An organic compound shows optical isomerism if it has a chiral carbon (an asymmetric carbon attached to four different groups) and lacks an internal plane of symmetry.

  2. Check each alkene option


Option A: 3-methyl-2-pentene

Structure:

CH3−CH=C(CH3)−CH2−CH3\text{CH}_3-\text{CH}=\text{C}(\text{CH}_3)-\text{CH}_2-\text{CH}_3CH3​−CH=C(CH3​)−CH2​−CH3​

At carbon-3, the double-bonded carbon is sp2sp^2sp2 hybridized, so it cannot be chiral.
No other carbon has four different substituents.

So, A is not optically active.


Option B: 4-methyl-1-pentene

Structure:

CH2=CH−CH2−CH(CH3)−CH3\text{CH}_2=\text{CH}-\text{CH}_2-\text{CH}(\text{CH}_3)-\text{CH}_3CH2​=CH−CH2​−CH(CH3​)−CH3​

Now check carbon-4: It is attached to:

  • H\text{H}H
  • CH3\text{CH}_3CH3​
  • another CH3\text{CH}_3CH3​
  • CH2−CH=CH2\text{CH}_2-\text{CH}=\text{CH}_2CH2​−CH=CH2​

Since two substituents are identical (CH3\text{CH}_3CH3​ and CH3\text{CH}_3CH3​), this carbon is not chiral.

So, B is not optically active.


Option C: 3-methyl-1-pentene

Structure:

CH2=CH−CH(CH3)−CH2−CH3\text{CH}_2=\text{CH}-\text{CH}(\text{CH}_3)-\text{CH}_2-\text{CH}_3CH2​=CH−CH(CH3​)−CH2​−CH3​

Check carbon-3: It is attached to:

  • H\text{H}H
  • CH3\text{CH}_3CH3​
  • CH2CH3\text{CH}_2\text{CH}_3CH2​CH3​
  • CH=CH2\text{CH}=\text{CH}_2CH=CH2​

These are four different groups, so carbon-3 is a chiral center.

Hence, C exhibits optical isomerism.


Option D: 2-methyl-2-pentene

Structure:

CH3−C(CH3)=CH−CH2−CH3\text{CH}_3-\text{C}(\text{CH}_3)=\text{CH}-\text{CH}_2-\text{CH}_3CH3​−C(CH3​)=CH−CH2​−CH3​

The double-bond carbon is sp2sp^2sp2 hybridized and cannot be chiral.
No other carbon has four different substituents.

So, D is not optically active.


  1. Final conclusion Only 3-methyl-1-pentene has a chiral carbon and therefore shows optical isomerism.
C\boxed{\text{C}}C​
  1. Comparison with stored correct answer
    Stored correct answer = C
    Derived answer = C
    So, they agree.
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