(a) When HBr adds across the double bond of 1,2-dimethylcyclopentene, the product is a mixture of the cis and trans isomers. Show why this addition is not stereospecific. (b) When 1,2-dimethylcyclopentene undergoes hydroboration–oxidation, one diastereomer of the product predominates. Show why this addition is stereospecific, and predict the stereochemistry of the major product.
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