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JEE Advanced levelNumerical answerDifficulty 3 of 3o3239

The dibromide shown has unspecified configuration at both stereocentres, i.e. it is the mixture of all its stereoisomers. It reacts completely with excess in DMF, with inversion at each carbon bearing Br. Count every configurational stereoisomer (optical isomers counted separately; a meso form counts once) of the dinitrile product constitution that is obtained from this mixture. Give your answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 3

The compound is 2,4-dibromopentane, with two stereocentres and a mirror-symmetric constitution: (R,R), (S,S) and meso (R,S). Each is converted by double inversion into a dinitrile of the matching type: (R,R) to (S,S), (S,S) to (R,R), and meso to meso. All three stereoisomers of 2,4-dimethylpentanedinitrile are therefore obtained (RDKit count: 3). Answer: 3.
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