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Basics of Organic Chemistry question

2021 · Shift 1 · Q2
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Basics of Organic Chemistry question

2021 · Shift 1 · Q2

JEE AdvancedChemistryBasics of Organic ChemistryMCQ+3 / −1
Among the following, the conformation that corresponds to the most stable conformation of meso-butane-2,3-diol is
  1. A
    JEE Advanced 2021 Paper 1 Online Chemistry - Basics of Organic Chemistry Question 27 English Option 1
  2. B
    JEE Advanced 2021 Paper 1 Online Chemistry - Basics of Organic Chemistry Question 27 English Option 2
  3. C
    JEE Advanced 2021 Paper 1 Online Chemistry - Basics of Organic Chemistry Question 27 English Option 3
  4. D
    JEE Advanced 2021 Paper 1 Online Chemistry - Basics of Organic Chemistry Question 27 English Option 4
View written solutionFree

Correct answer: B

Step-by-Step Solution:

  1. Identify the Molecule: The molecule is meso-butane-2,3-diol. Its structure is CH3-CH(OH)-CH(OH)-CH3. The term "meso" indicates that the molecule has chiral centers (C2 and C3) but is achiral overall due to an internal plane of symmetry in at least one of its conformations.

  2. Analyze Factors Affecting Conformational Stability: The stability of a conformation is determined by several factors:

    • Torsional Strain: Staggered conformations are significantly more stable than eclipsed conformations.
    • Steric Strain (van der Waals repulsion): Repulsion between bulky groups. Conformations where bulky groups are far apart (anti) are more stable than those where they are close (gauche).
    • Intramolecular Hydrogen Bonding: When groups like -OH are close enough (gauche), they can form an intramolecular hydrogen bond, which is a strong stabilizing interaction.
  3. Evaluate the Given Conformations (Newman Projections): The question provides four Newman projections looking down the C2-C3 bond. The substituents on each carbon are a methyl group (CH3), a hydroxyl group (OH), and a hydrogen atom (H).

    • Option D: This is an eclipsed conformation. The groups on the front carbon are directly in front of the groups on the back carbon. Eclipsed conformations have high torsional and steric strain, making them the least stable. Therefore, Option D can be eliminated.

    • Options A, B, and C: These are all staggered conformations, which are more stable than the eclipsed form. We need to compare their relative stabilities.

      • Conformation A: The two hydroxyl (OH) groups are anti (180° apart). The two methyl (CH3) groups are gauche (60° apart). While the anti position for OH groups minimizes their interaction, the gauche interaction between the two bulky CH3 groups causes significant steric strain. Also, no intramolecular hydrogen bonding is possible between the anti OH groups.

      • Conformation B: The two bulky methyl (CH3) groups are anti to each other. This is the most favorable arrangement for the largest groups as it minimizes steric repulsion. The two hydroxyl (OH) groups are gauche to each other. This arrangement allows for intramolecular hydrogen bonding between the hydrogen of one OH group and the oxygen of the other. This hydrogen bond is a strong stabilizing force. The combination of minimized steric strain (anti CH3 groups) and the stabilizing effect of intramolecular hydrogen bonding makes this conformation highly stable.

      • Conformation C: Both the methyl (CH3) groups and the hydroxyl (OH) groups are in gauche positions. While the gauche OH groups can form a stabilizing hydrogen bond (similar to B), the gauche interaction between the bulky CH3 groups introduces significant steric strain (similar to A). The destabilizing steric strain from the gauche methyl groups makes this conformation less stable than conformation B.

  4. Compare Stabilities and Conclude:

    • Stability Order: Eclipsed << Staggered So, D is the least stable.

    • Comparing staggered conformations:

      • Stability of B vs. A: B has CH3 groups anti (low steric strain) and H-bonding (stabilizing). A has CH3 groups gauche (high steric strain) and no H-bonding. Thus, B is much more stable than A.
      • Stability of B vs. C: B has CH3 groups anti (low steric strain). C has CH3 groups gauche (high steric strain). Although both can have H-bonding, the lower steric strain in B makes it more stable than C.

    Therefore, conformation B, which features the bulkiest groups (CH3) in an anti arrangement and allows for intramolecular hydrogen bonding between the gauche OH groups, is the most stable conformation of meso-butane-2,3-diol.

Final Answer: The most stable conformation is B.

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