JEE Main · 2021 · Shift-IIeasyHC-014

Arrange the following conformational isomers of n-butane in order of their increasing potential energy:

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

Arrange the following conformational isomers of n-butane in order of their increasing potential energy: image

Options
  1. a

    I < III < IV < II

  2. b

    I < IV < III < II

  3. c

    II < III < IV < I

  4. d

    II < IV < III < I

Correct Answera

I < III < IV < II

Detailed Solution

Step 1: Identify the four conformations of n-butane

For n-butane (\ceCH3CH2CH2CH3\ce{CH3CH2CH2CH3}), the Newman projection about the C2–C3 bond gives:

  • Conformation I (Anti): Dihedral angle = 180°, two \ceCH3\ce{CH3} groups are anti — most stable (lowest PE)
  • Conformation II (Fully eclipsed): Dihedral angle = 0°, two \ceCH3\ce{CH3} groups eclipsed — least stable (highest PE)
  • Conformation III (Gauche): Dihedral angle = 60°, \ceCH3\ce{CH3} groups gauche — second most stable
  • Conformation IV (Partially eclipsed): Dihedral angle = 120°, \ceCH3\ce{CH3} eclipses \ceH\ce{H} — between gauche and fully eclipsed

Step 2: Order by potential energy (increasing)

Potential energy order (lowest to highest): Anti (I)<Gauche (III)<Partially eclipsed (IV)<Fully eclipsed (II)\text{Anti (I)} < \text{Gauche (III)} < \text{Partially eclipsed (IV)} < \text{Fully eclipsed (II)}

Step 3: Match to answer choices

Increasing PE: I < III < IV < II → Option (a)

Key Points to Remember:

  • Anti (180°) = most stable for n-butane; gauche (60°) has 3.8 kJ/mol more PE
  • Fully eclipsed (0°) = least stable; 19 kJ/mol above anti
  • Partially eclipsed (120°) is between gauche and fully eclipsed
  • Stability order: anti > gauche > partially eclipsed > fully eclipsed

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