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JEE Advanced levelNumerical answerDifficulty 3 of 3o1244

The meso diol shown reacts with benzaldehyde under acid catalysis to give a cyclic acetal (1,3-dioxolane) whose two ring stereocentres derived from the diol keep their configuration. Counting configurational stereoisomers of the acetal in which those two centres stay as drawn, how many stereoisomers can form? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 2

Butane-2,3-diol drawn is the meso (2R,3S) isomer, so its two methyl-bearing ring carbons keep configurations that put the methyls cis in the ring. The new acetal carbon C2 carries phenyl, hydrogen and two ring oxygens, and phenyl can be cis or trans to the methyls. RDKit enumeration with the diol centres fixed gives 2 distinct stereoisomers (both achiral, diastereomers).
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