Which of the following molecules do not rotate the plane of plane-polarized light?

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Correct Answer: A. 1, 4
Rotation of plane polarized light is indicative of a chiral molecule. If not, the compounds must be meso or achiral. Compounds 1 and 4 are meso compounds, which, despite having two or more stereocenters, are not chiral (superposable on its mirror image). Compounds 2 and 3 are chiral molecules.
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