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Basics of Organic Chemistry question

2021 · 22 Jul · Shift 2 · Q8
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Basics of Organic Chemistry question

2021 · 22 Jul · Shift 2 · Q8

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Which of the following molecules does not show stereo isomerism?
  1. A
    3, 4-Dimethylhex-3-ene
  2. B
    3-Methylhex-1-ene
  3. C
    3-Ethylhex-3-ene
  4. D
    4-Methylhex-1-ene
View written solutionFree

Correct answer: C

  1. Idea: A molecule can show stereoisomerism if it has either:
    • a geometrical isomerism element (like E/ZE/ZE/Z or cis/trans around a double bond), or
    • an optical isomerism element (a chiral center).

We check each option.


  1. Option A: 3,4-Dimethylhex-3-ene

Structure around the double bond: CH3CH2C(CH3)=C(CH3)CH2CH3\text{CH}_3\text{CH}_2\text{C}(\text{CH}_3)=\text{C}(\text{CH}_3)\text{CH}_2\text{CH}_3CH3​CH2​C(CH3​)=C(CH3​)CH2​CH3​

At carbon-3 of the double bond, the two groups are:

  • CH3\text{CH}_3CH3​
  • C2H5\text{C}_2\text{H}_5C2​H5​

At carbon-4 of the double bond, the two groups are:

  • CH3\text{CH}_3CH3​
  • C2H5\text{C}_2\text{H}_5C2​H5​

Since each double-bond carbon has two different groups, geometrical isomerism (E/ZE/ZE/Z) is possible.

So, A shows stereoisomerism.


  1. Option B: 3-Methylhex-1-ene

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

Check geometrical isomerism:

  • At carbon-1 of the double bond, it is CH2=\text{CH}_2=CH2​=, so one carbon has two identical H atoms.
  • Therefore, no geometrical isomerism.

Check chirality at carbon-3: Carbon-3 is attached to

  • H\text{H}H
  • CH3\text{CH}_3CH3​
  • CH=CH2\text{CH}=\text{CH}_2CH=CH2​
  • CH2CH2CH3\text{CH}_2\text{CH}_2\text{CH}_3CH2​CH2​CH3​

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

Hence, B shows optical isomerism, so it shows stereoisomerism.


  1. Option C: 3-Ethylhex-3-ene

Structure: CH3CH2−C(C2H5)=CH−CH2CH3\text{CH}_3\text{CH}_2-\text{C}(\text{C}_2\text{H}_5)=\text{CH}-\text{CH}_2\text{CH}_3CH3​CH2​−C(C2​H5​)=CH−CH2​CH3​

More clearly, at carbon-3 of the double bond, the attached groups are:

  • left side chain: C2H5\text{C}_2\text{H}_5C2​H5​
  • substituent: C2H5\text{C}_2\text{H}_5C2​H5​

So carbon-3 has two identical ethyl groups attached.

For geometrical isomerism, each double-bond carbon must have two different groups. That fails here. Thus, no geometrical isomerism.

Now check optical isomerism:

  • There is no chiral center, because no tetrahedral carbon has four different groups.

Hence, C does not show stereoisomerism.


  1. Option D: 4-Methylhex-1-ene

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

Check geometrical isomerism:

  • Double bond is terminal (CH2=CH−\text{CH}_2=\text{CH}-CH2​=CH−), so one alkene carbon has two H atoms.
  • Therefore, no geometrical isomerism.

Check chirality at carbon-4: Carbon-4 is attached to

  • H\text{H}H
  • CH3\text{CH}_3CH3​
  • CH2CH3\text{CH}_2\text{CH}_3CH2​CH3​
  • CH2CH=CH2\text{CH}_2\text{CH}=\text{CH}_2CH2​CH=CH2​

These are four different groups, so carbon-4 is a chiral center.

Hence, D shows optical isomerism.


  1. Conclusion

Only option C does not show any stereoisomerism.

Therefore, the correct answer is: C\boxed{\text{C}}C​


  1. Comparison with stored correct answer

Stored correct answer: C

My derived answer: C

They agree.

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