PMDC Verified Question 48 of 83
Which of the following will have a meso isomer?
A
2-chlorobutane
B
2,3-dichlorobutane
C
2,3-dichloropentane
D
1,2-dichlobutane
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option B: 2,3-dichlorobutane
Concept:

A meso compound is an achiral molecule that contains multiple chiral centers but possesses an internal plane of symmetry.

Solution:

  • To have a plane of symmetry, the two halves of the molecule must be identical.


  • 2,3-dichlorobutane: \( \text{CH}_3\text{--CH}(\text{Cl})\text{--CH}(\text{Cl})\text{--CH}_3 \). It has two chiral centers (C2 and C3) with identical substituent sets.


  • In the (2R, 3S) or (2S, 3R) configuration, the molecule can be rotated to show a plane of symmetry splitting the C2-C3 bond.


  • Thus, it exists as a meso isomer.


Why other options are incorrect:

2-chlorobutane and 1,2-dichlorobutane lack symmetric halves. 2,3-dichloropentane has different ends (an ethyl group vs a methyl group), preventing an internal plane of symmetry.

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