MolSynapsequestion bank
MolSynapse / Question bank / Stereoisomerism / Enantiomers versus diastereomers of drawn pairs
JEE Advanced levelSingle correct optionDifficulty 3 of 3st303

The two structures shown (left and right) are stereoisomers of 2,4-dibromopentane drawn with opposite wedge patterns at both stereocentres. They are related as

  1. Aenantiomers
  2. Bconstitutional isomers
  3. Cdiastereomers
  4. Didentical (same compound)

Answer: D

The left structure has descriptors at C2 and at C4; reversing both wedges gives at C2 and at C4 in the right structure. Since C2 and C4 carry identical groups, numbering the chain from the other end converts (2R,4S) into (2S,4R). Both structures are the meso form of 2,4-dibromopentane, which has a mirror plane through C3. A meso compound is superimposable on its mirror image, so the two drawings represent the same compound.
Practice Stereoisomerism More on Enantiomers versus diastereomers of drawn pairs

More questions on Enantiomers versus diastereomers of drawn pairs