JEE Challenger
More from Organic Chemistry - Basic Principles

Determine Correct Stereochemical Relationships Among Given Molecules

Which of the given statement(s) about N,O,P\mathbf{N}, \mathbf{O}, \mathbf{P} and Q\mathbf{Q} with respect to M\mathbf{M} is (are) correct ?

Question Diagram 1

Options

A

M\mathbf{M} and N\mathbf{N} are non-mirror image stereoisomers

Correct
B

M\mathbf{M} and O\mathbf{O} are identical

Correct
C

M\mathbf{M} and P\mathbf{P} are enantiomers

Correct
D

M\mathbf{M} and Q\mathbf{Q} are identical

Step-by-Step Solution

To determine the stereochemical relationships among the given molecules M,N,O,P,\mathbf{M}, \mathbf{N}, \mathbf{O}, \mathbf{P}, and Q\mathbf{Q}, we assign absolute configurations (R/S)(R/S) to the two chiral centers in each structure using the Cahn-Ingold-Prelog (CIP) priority rules.


1. Priority Rules for the Chiral Centers

The given compound is 1-chloropropane-1,2-diol with two chiral carbons, denoted as C1\text{C}_1 and C2\text{C}_2:

  1. At C1\text{C}_1 (carbon attached to −Cl,−OH,−H,-\text{Cl}, -\text{OH}, -\text{H}, and C2\text{C}_2): Priority 1: −Cl>Priority 2: −OH>Priority 3: −C2>Priority 4: −H\text{Priority 1: } -\text{Cl} > \text{Priority 2: } -\text{OH} > \text{Priority 3: } -\text{C}_2 > \text{Priority 4: } -\text{H}

  2. At C2\text{C}_2 (carbon attached to −OH,−C1,−CH3,-\text{OH}, -\text{C}_1, -\text{CH}_3, and −H-\text{H}): Priority 1: −OH>Priority 2: −C1>Priority 3: −CH3>Priority 4: −H\text{Priority 1: } -\text{OH} > \text{Priority 2: } -\text{C}_1 > \text{Priority 3: } -\text{CH}_3 > \text{Priority 4: } -\text{H}


2. Absolute Configuration Analysis

Molecule M:

  • Front carbon (C2\text{C}_2): −CH3-\text{CH}_3 is at the bottom, −OH-\text{OH} is top-left, −H-\text{H} is top-right. Viewing along the C2−C1\text{C}_2-\text{C}_1 bond gives the configuration 2R2R.
  • Back carbon (C1\text{C}_1): −HO-\text{HO} is top-left, −H-\text{H} is top-right, −Cl-\text{Cl} is bottom-right. Determining priority path yields the configuration 1S1S. M  ⟹  (1S,2R)\mathbf{M} \implies (1S, 2R)

Molecule N:

  • Front carbon (C1\text{C}_1): −Cl-\text{Cl} is at the bottom, −H-\text{H} is on the left, −OH-\text{OH} is on the right, which gives the configuration 1S1S.

  • Back carbon (C2\text{C}_2): −HO-\text{HO} is top-left, −H-\text{H} is top-right, −CH3-\text{CH}_3 is on the right, which gives the configuration 2S2S. N  ⟹  (1S,2S)\mathbf{N} \implies (1S, 2S)

  • Relationship (M\mathbf{M} vs N\mathbf{N}): M (1S,2R)\mathbf{M}\,(1S, 2R) and N (1S,2S)\mathbf{N}\,(1S, 2S) differ at one chiral center. They are non-superimposable, non-mirror image stereoisomers, i.e., diastereomers (non-mirror image stereoisomers).
      ⟹  \implies Statement (A) is CORRECT.


Molecule O:

  • Rotating the back carbon (C1\text{C}_1) of molecule M\mathbf{M} by 120∘120^\circ counter-clockwise around the C1−C2\text{C}_1-\text{C}_2 single bond yields molecule O\mathbf{O}.

  • Since bond rotation does not alter absolute configuration: O  ⟹  (1S,2R)\mathbf{O} \implies (1S, 2R)

  • Relationship (M\mathbf{M} vs O\mathbf{O}): Both molecules have the configuration (1S,2R)(1S, 2R) and represent conformers of the same compound. Thus, M\mathbf{M} and O\mathbf{O} are identical.
      ⟹  \implies Statement (B) is CORRECT.


Molecule P:

  • Front carbon (C2\text{C}_2): −CH3-\text{CH}_3 is at 12 o'clock, −OH-\text{OH} is at 8 o'clock, −H-\text{H} is at 4 o'clock, yielding configuration 2S2S.

  • Back carbon (C1\text{C}_1): −OH-\text{OH} is at 2 o'clock, −Cl-\text{Cl} is at 6 o'clock, −H-\text{H} is at 10 o'clock, yielding configuration 1R1R. P  ⟹  (1R,2S)\mathbf{P} \implies (1R, 2S)

  • Relationship (M\mathbf{M} vs P\mathbf{P}): M (1S,2R)\mathbf{M}\,(1S, 2R) and P (1R,2S)\mathbf{P}\,(1R, 2S) have all chiral centers inverted. They are non-superimposable mirror images of each other, i.e., enantiomers.
      ⟹  \implies Statement (C) is CORRECT.


Molecule Q:

  • Front carbon (C2\text{C}_2): Configuration is 2S2S (identical to P\mathbf{P}).

  • Back carbon (C1\text{C}_1): −H-\text{H} is at 2 o'clock, −Cl-\text{Cl} is at 6 o'clock, −OH-\text{OH} is at 10 o'clock, yielding configuration 1S1S. Q  ⟹  (1S,2S)\mathbf{Q} \implies (1S, 2S)

  • Relationship (M\mathbf{M} vs Q\mathbf{Q}): M (1S,2R)\mathbf{M}\,(1S, 2R) and Q (1S,2S)\mathbf{Q}\,(1S, 2S) are diastereomers, not identical.
      ⟹  \implies Statement (D) is INCORRECT.


Conclusion

The correct options are A, B, and C.