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JEE Advanced levelNumerical answerDifficulty 3 of 3o3253

The secondary bromide shown (configuration not specified) is hydrolysed in water by an pathway, and its cation undergoes the favourable 1,2-methyl shift. Ignoring elimination, count every configurational stereoisomer (optical isomers counted separately) of all alcohols that can form by capture of the unrearranged and rearranged cations. Give your answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 3

The compound is 2-bromo-3,3-dimethylbutane. Water captures the unrearranged cation to give 3,3-dimethylbutan-2-ol (one stereocentre, 2 enantiomers) and the rearranged tertiary cation to give 2,3-dimethylbutan-2-ol (no stereocentre, 1 compound). RDKit enumeration: 2 + 1 = 3. Answer: 3.
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