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Basics of Organic Chemistry question

2004 · Shift 0 · Q24
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Basics of Organic Chemistry question

2004 · Shift 0 · Q24

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Amongst the following compounds, the optically active alkane having lowest molecular mass is
  1. A
    AIEEE 2004 Chemistry - Basics of Organic Chemistry Question 237 English Option 1
  2. B
    AIEEE 2004 Chemistry - Basics of Organic Chemistry Question 237 English Option 2
  3. C
    AIEEE 2004 Chemistry - Basics of Organic Chemistry Question 237 English Option 3
  4. D
    AIEEE 2004 Chemistry - Basics of Organic Chemistry Question 237 English Option 4
View written solutionFree

Correct answer: A

  1. Key idea: condition for optical activity in an alkane

An alkane will be optically active if it contains a chiral carbon atom, i.e. a carbon attached to four different groups.

  1. Check the smallest possible alkane formulas
  • CH4\mathrm{CH_4}CH4​, C2H6\mathrm{C_2H_6}C2​H6​, C3H8\mathrm{C_3H_8}C3​H8​: clearly achiral.
  • C4H10\mathrm{C_4H_{10}}C4​H10​ (butane, isobutane): no chiral carbon.
  • C5H12\mathrm{C_5H_{12}}C5​H12​ isomers:
    • n-pentane: achiral
    • isopentane (2-methylbutane): achiral
    • neopentane (2,2-dimethylpropane): achiral

So no optically active alkane exists up to molecular formula C5H12\mathrm{C_5H_{12}}C5​H12​.

  1. Now examine C6H14\mathrm{C_6H_{14}}C6​H14​ isomers

Possible isomers include:

  • n-hexane
  • 2-methylpentane
  • 3-methylpentane
  • 2,2-dimethylbutane
  • 2,3-dimethylbutane

Check for chirality:

  • In 2-methylpentane, the possible substituted carbon has two identical methyl groups somewhere in comparison, so no carbon has four different substituents.
  • In 3-methylpentane, the central carbon is attached to two identical ethyl groups, so achiral.
  • In 2,2-dimethylbutane, no chiral center.
  • In 2,3-dimethylbutane, each middle carbon is attached to identical groups in a symmetric structure, so achiral.

Hence, all C6H14\mathrm{C_6H_{14}}C6​H14​ isomers are achiral.

  1. Examine C7H16\mathrm{C_7H_{16}}C7​H16​ isomers

Consider 3-methylhexane:

CH3−CH2−CH(CH3)−CH2−CH2−CH3\mathrm{CH_3-CH_2-CH(CH_3)-CH_2-CH_2-CH_3}CH3​−CH2​−CH(CH3​)−CH2​−CH2​−CH3​

At carbon-3, the four groups attached are:

  • H\mathrm{H}H
  • CH3\mathrm{CH_3}CH3​
  • C2H5\mathrm{C_2H_5}C2​H5​
  • C3H7\mathrm{C_3H_7}C3​H7​

These are four different groups, so carbon-3 is chiral. Therefore, 3-methylhexane is optically active.

Thus, the alkane with the lowest molecular mass that can be optically active has molecular formula:

C7H16\mathrm{C_7H_{16}}C7​H16​
  1. Conclusion

The required compound is 3-methylhexane (or equivalently the option corresponding to the first optically active alkane).

Since the actual option structures are not visible and the stored correct answer is A, I compare with the conceptual result: if option A is 3-methylhexane, then the stored answer is correct.

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