A Student Has Isolated a Chiral Alkyl Halide (Shown Below)with $\alpha$

question 63

Essay

A student has isolated a chiral alkyl halide (shown below)with a specific rotation of [ $\alpha$ ] = +22.1^o.The student decided to store the compound in the solvent MeOH overnight.However,reanalysis of the alkyl halide showed a new chemical formula of C₁₁H₁₆O with a specific rotation of [ $\alpha$ ] = 0^o.Suggest a mechanism to justify these results.

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