Solving Anti-Markovnikov Addition Rxns with Peroxide

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SUMMARY

The discussion focuses on the anti-Markovnikov addition of HBr to alkenes in the presence of peroxides, specifically addressing the stereochemistry of the resulting products. The reactions analyzed include 2-methylpropene, 1-methylcyclopropene, and 1-phenylpropene, all yielding racemic mixtures due to the non-stereospecific nature of the addition. The participants confirm that the addition generates a maximum of four different products for the second reaction, although the author initially miscalculated the product count. The ambiguity in the textbook regarding stereochemistry is noted as a potential source of confusion.

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I'm trying to solve some organic chem reactions out of a new textbook with an answer key that's confusing me. All three rxns involve anti-markovnikov addition of HBr to an alkene using a peroxide. A peroxide radical generates a bromine radical, the electrophile which then adds to the least subsituted carbon. I would think that these rxns would be non-sterospecific, thus generating a maximum of four different products. Here are the reactions and what I think the answers should be.

I don't care about exact answers I'm just want to confirm stereochemistry:

1) 2-methylpropene +HBr + peroxide--->a racemic mix of two products, right?

2) 1-methylcyclopropene+HBr+peroxide---> 2 different racemic mixtures, four total different products

3) 1-phenylpropene + HBr +peroxide---->again, a racemic mixture of two product


My book is ambiguous in it's description of stereochem for the products, perhaps because it's an advanced text which just assumes this stuff is obvious.
 
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edit: OOPS! My bad...
I don't get 4 products for 2). Do you postulate that the double bond migrates?
 

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