MCQMediumJEE 2025Isomerism (Structural, Stereoisomerism)

JEE Chemistry 2025 Question with Solution

Identify the number of structure/s from the following which can be correlated to D-glyceraldehyde.

Four Fischer projection structures labeled A, B, C and D showing aldehyde and hydroxyl group arrangements for stereochemical comparison with D-glyceraldehyde.
  • A

    four

  • B

    three

  • C

    two

  • D

    one

Answer

Correct answer:C

Step-by-step solution

Standard Method

Given: Four structures are to be checked for correlation with D-glyceraldehyde.

Find: The number of structures that can be correlated to D-glyceraldehyde.

The solution states that D-glyceraldehyde is identified by the Fischer projection in which the hydroxyl group at the relevant chiral center is on the right side. It then compares the given structures one by one.

From the extracted comparison:

  1. Structure A does not match D-glyceraldehyde.
  2. Structure B matches D-glyceraldehyde.
  3. Structure C matches D-glyceraldehyde.
  4. Structure D does not match D-glyceraldehyde.

Therefore, the number of structures correlated to D-glyceraldehyde is 22.

The correct option is C.

Note: The prose inside the solution mentions three, but that contradicts both the listed matching structures (B and C only) and the solution stating the correct option is C. Hence the defensible conclusion from the provided solution content is two.

Using the Fischer projection criterion

Given: Correlation is to be made with D-glyceraldehyde using the Fischer projection idea.

Find: How many of the shown structures have the same relevant stereochemical correlation.

The hint says to check the configuration at the chiral center. The extracted solution further states:

  • D-glyceraldehyde has a chiral center.
  • In its Fischer projection, the hydroxyl group is on the right.

Now apply this criterion to the listed structures as described in the solution:

  • A: does not match.
  • B: hydroxyl group on the second carbon is on the right, so it matches.
  • C: hydroxyl group on the second carbon is on the right, so it matches.
  • D: does not match.

Hence, exactly two structures correlate to D-glyceraldehyde.

Therefore, the correct answer is 22, that is, option C.

Common mistakes

  • Checking all hydroxyl groups instead of the relevant chiral-center configuration. This is wrong because correlation to D-glyceraldehyde is decided by the stereochemical reference used in the Fischer projection. Instead, compare the specified chiral center in the correct orientation.

  • Trusting the isolated word three in the provided explanation without reconciling it with the structure-wise analysis. This is wrong because the same solution text marks only B and C as matching and the solution gives option C. Instead, use the explicit structure-by-structure conclusion.

  • Ignoring Fischer projection orientation rules. This is wrong because reversing or rotating a Fischer projection improperly can change the apparent left-right position of substituents. Instead, compare the structures using the standard Fischer convention.

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