JEE AdvancedChemistryBasics of Organic ChemistryMultiple correct+4 / −2
Among the given options, the compound(s) in which all the atoms are in one plane in all the possible conformations (if any) is(are)
- A

- B

- C= C = 0
- D= C =
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Correct answer: B, C
To determine which of the given compounds have all atoms in one plane in all possible conformations, we need to analyze the geometry and conformational flexibility of each molecule.
Step 1: Analyze Option A (Biphenyl)
- Structure: Biphenyl consists of two benzene rings connected by a carbon-carbon single bond.
- Planarity of Rings: Each benzene ring is individually planar because all its carbon atoms are hybridized.
- Conformations: There is free rotation around the C-C single bond connecting the two rings. This rotation leads to different conformations.
- Steric Hindrance: In the gas phase, the most stable conformation is one where the two rings are twisted relative to each other by about 44 degrees. This twisted conformation is non-planar. The reason for this twist is to minimize the steric repulsion between the hydrogen atoms on the ortho positions of the two rings.
- Conclusion: Since biphenyl exists in non-planar conformations, not all of its atoms lie in a single plane in all possible conformations. Therefore, option A is incorrect.
Step 2: Analyze Option B (Naphthalene)
- Structure: Naphthalene is an aromatic hydrocarbon consisting of two fused benzene rings.
- Hybridization: All ten carbon atoms in the naphthalene molecule are hybridized.
- Rigidity and Planarity: The fused ring system makes the molecule rigid. There are no single bonds around which significant rotation can occur, so there is essentially only one conformation.
- Geometry: Due to the hybridization of all carbon atoms and the fused ring structure, the entire molecule, including all carbon and hydrogen atoms, is planar.
- Conclusion: Since naphthalene has a single, rigid, planar conformation, all its atoms are in one plane. Therefore, option B is correct.
Step 3: Analyze Option C (Ketene, )
- Structure: Ketene has the structure .
- Hybridization:
- The central carbon atom () is involved in two double bonds, so it is hybridized.
- The terminal carbon atom () is involved in one double bond and two single bonds, so it is hybridized.
- Geometry:
- The hybridization of the central carbon () means that the atoms bonded to it ( and O) are arranged linearly. Thus, the skeleton is linear.
- The hybridization of the terminal carbon () means that the two hydrogen atoms and the central carbon atom () attached to it lie in the same plane.
- Since the group is planar, and the oxygen atom is collinear with the bond, the entire molecule must be planar.
- Conformations: The presence of double bonds restricts rotation, making the molecule rigid. It exists in only one conformation.
- Conclusion: Since the single conformation of ketene is planar, all its atoms are in one plane. Therefore, option C is correct.
Step 4: Analyze Option D (Allene, )
- Structure: Allene has the structure .
- Hybridization:
- The central carbon atom () is hybridized.
- The terminal carbon atoms ( and ) are hybridized.
- Geometry:
- The hybridization of results in a linear skeleton.
- The central carbon atom () uses two perpendicular p-orbitals (e.g., and ) to form the two -bonds with the terminal carbons.
- The plane of the group is determined by the p-orbital used for its -bond. If uses to bond with , the plane will be the xz-plane.
- Consequently, must use its other p-orbital, , to bond with . This forces the plane to be the xy-plane.
- The two terminal groups lie in planes that are perpendicular to each other.
- Conclusion: Allene is a non-planar molecule. Since its only conformation is non-planar, it does not satisfy the condition. Therefore, option D is incorrect.
Final Answer Summary:
- A: Not always planar. Incorrect.
- B: Rigid and planar. Correct.
- C: Rigid and planar. Correct.
- D: Rigid and non-planar. Incorrect.
The compounds in which all atoms are in one plane in all possible conformations are Naphthalene (B) and Ketene (C).
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