destroyer orgo # 19

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DentalDorito

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This is a bridged hexane......how can both D's be straight down rather that one axial and one equatorial making them syn? Basically I think C book says B.....please help me understand
 
This is a bridged hexane......how can both D's be straight down rather that one axial and one equatorial making them syn? Basically I think C book says B.....please help me understand

D2 reacting with Pt adds in SYN orientation.
 
This is an interesting question. I would have also picked answer C since that shows "cis" or syn addition to the chair if that molecule is a chair confirmation. Otherwise B is right because of that bulky group (preferential attack).

anyone else have suggestion?
 
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