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Basics of Organic Chemistry question

2011 · Shift 1 · Q15
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Basics of Organic Chemistry question

2011 · Shift 1 · Q15

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)
  1. A
    IIT-JEE 2011 Paper 1 Offline Chemistry - Basics of Organic Chemistry Question 17 English Option 1
  2. B
    IIT-JEE 2011 Paper 1 Offline Chemistry - Basics of Organic Chemistry Question 17 English Option 2
  3. C
    H2CH_2CH2​C = C = 0
  4. D
    H2CH_2CH2​C = C = CH2CH_2CH2​
View written solutionFree

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)

Biphenyl
  1. Structure: Biphenyl consists of two benzene rings connected by a carbon-carbon single bond.
  2. Planarity of Rings: Each benzene ring is individually planar because all its carbon atoms are sp2sp^2sp2 hybridized.
  3. Conformations: There is free rotation around the C-C single bond connecting the two rings. This rotation leads to different conformations.
  4. 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.
  5. 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)

Naphthalene
  1. Structure: Naphthalene is an aromatic hydrocarbon consisting of two fused benzene rings.
  2. Hybridization: All ten carbon atoms in the naphthalene molecule are sp2sp^2sp2 hybridized.
  3. 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.
  4. Geometry: Due to the sp2sp^2sp2 hybridization of all carbon atoms and the fused ring structure, the entire molecule, including all carbon and hydrogen atoms, is planar.
  5. 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, H2C=C=OH_2C = C = OH2​C=C=O)

Ketene
  1. Structure: Ketene has the structure H2Ca=Cb=OH_2C_a=C_b=OH2​Ca​=Cb​=O.
  2. Hybridization:
    • The central carbon atom (CbC_bCb​) is involved in two double bonds, so it is spspsp hybridized.
    • The terminal carbon atom (CaC_aCa​) is involved in one double bond and two single bonds, so it is sp2sp^2sp2 hybridized.
  3. Geometry:
    • The spspsp hybridization of the central carbon (CbC_bCb​) means that the atoms bonded to it (CaC_aCa​ and O) are arranged linearly. Thus, the Ca−Cb−OC_a-C_b-OCa​−Cb​−O skeleton is linear.
    • The sp2sp^2sp2 hybridization of the terminal carbon (CaC_aCa​) means that the two hydrogen atoms and the central carbon atom (CbC_bCb​) attached to it lie in the same plane.
    • Since the H2CaH_2C_aH2​Ca​ group is planar, and the oxygen atom is collinear with the Ca−CbC_a-C_bCa​−Cb​ bond, the entire molecule must be planar.
  4. Conformations: The presence of double bonds restricts rotation, making the molecule rigid. It exists in only one conformation.
  5. 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, H2C=C=CH2H_2C = C = CH_2H2​C=C=CH2​)

Allene
  1. Structure: Allene has the structure H2Ca=Cb=CcH2H_2C_a=C_b=C_cH_2H2​Ca​=Cb​=Cc​H2​.
  2. Hybridization:
    • The central carbon atom (CbC_bCb​) is spspsp hybridized.
    • The terminal carbon atoms (CaC_aCa​ and CcC_cCc​) are sp2sp^2sp2 hybridized.
  3. Geometry:
    • The spspsp hybridization of CbC_bCb​ results in a linear Ca−Cb−CcC_a-C_b-C_cCa​−Cb​−Cc​ skeleton.
    • The central carbon atom (CbC_bCb​) uses two perpendicular p-orbitals (e.g., pyp_ypy​ and pzp_zpz​) to form the two π\piπ-bonds with the terminal carbons.
    • The plane of the H2CaH_2C_aH2​Ca​ group is determined by the p-orbital used for its π\piπ-bond. If CbC_bCb​ uses pyp_ypy​ to bond with CaC_aCa​, the H2CaH_2C_aH2​Ca​ plane will be the xz-plane.
    • Consequently, CbC_bCb​ must use its other p-orbital, pzp_zpz​, to bond with CcC_cCc​. This forces the H2CcH_2C_cH2​Cc​ plane to be the xy-plane.
    • The two terminal CH2CH_2CH2​ groups lie in planes that are perpendicular to each other.
  4. 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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