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Biomolecules question

2015 · Shift 1 · Q16
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Biomolecules question

2015 · Shift 1 · Q16

JEE AdvancedChemistryBiomoleculesMultiple correct+4 / −2
The structure of D-(+)-glucose is JEE Advanced 2015 Paper 1 Offline Chemistry - Biomolecules Question 13 English The structure of L-(−-−)-glucose is
  1. A
    JEE Advanced 2015 Paper 1 Offline Chemistry - Biomolecules Question 13 English Option 1
  2. B
    JEE Advanced 2015 Paper 1 Offline Chemistry - Biomolecules Question 13 English Option 2
  3. C
    JEE Advanced 2015 Paper 1 Offline Chemistry - Biomolecules Question 13 English Option 3
  4. D
    JEE Advanced 2015 Paper 1 Offline Chemistry - Biomolecules Question 13 English Option 4
View written solutionFree

Correct answer: A

  1. Interpret the question

    The question asks for the structures of:

    • D-(+)-glucose\text{D-(+)-glucose}D-(+)-glucose
    • L-(-)-glucose\text{L-(-)-glucose}L-(-)-glucose

    This is a stereochemistry question about D/L configuration and optical rotation.

  2. Key concept: D and L notation

    For monosaccharides, D/L is assigned by comparing the configuration at the chiral carbon farthest from the aldehyde group (the penultimate carbon) with glyceraldehyde.

    • In D-glucose, the −OH-OH−OH on the penultimate carbon (C5C_5C5​ in glucose) is on the right in the Fischer projection.
    • In L-glucose, the −OH-OH−OH on C5C_5C5​ is on the left.
  3. Fischer projection of D-glucose

    For aldohexose glucose, the standard Fischer projection has the following OHOHOH arrangement from C2C_2C2​ to C5C_5C5​:

    D-glucose: Right, Left, Right, Right\text{D-glucose: Right, Left, Right, Right}D-glucose: Right, Left, Right, Right

    So its Fischer projection is:

    • C2C_2C2​: OHOHOH on right
    • C3C_3C3​: OHOHOH on left
    • C4C_4C4​: OHOHOH on right
    • C5C_5C5​: OHOHOH on right
  4. Fischer projection of L-glucose

    L-glucose is the mirror image of D-glucose. Therefore the OHOHOH positions from C2C_2C2​ to C5C_5C5​ become:

    L-glucose: Left, Right, Left, Left\text{L-glucose: Left, Right, Left, Left}L-glucose: Left, Right, Left, Left

  5. About (+)(+)(+) and (−)(-)(−) signs

    The symbols (+)(+)(+) and (−)(-)(−) indicate direction of optical rotation, while D/L indicates configuration. For glucose, it is known that:

    • D-glucose is dextrorotatory: D-(+)-glucose\text{D-(+)-glucose}D-(+)-glucose
    • L-glucose is levorotatory: L-(-)-glucose\text{L-(-)-glucose}L-(-)-glucose

    Hence the required structures are the standard Fischer projections of D-glucose and its mirror image L-glucose.

  6. Matching with options

    Since the actual option figures are not visible in the prompt, we rely on the stored answer and the known stereochemistry. The correct option must be the one showing:

    • D-(+)-glucose as RLRRRLRRRLRR (from C2C_2C2​ to C5C_5C5​ in terms of side of OHOHOH = right, left, right, right)
    • L-(-)-glucose as its mirror image LRLLLRLLLRLL

    The stored correct answer is A, so option A must correspond to these structures.

  7. Conclusion

    Therefore, the correct answer is A.

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