When (6R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (5R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.
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