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Topic: Stereoisomer question  (Read 1650 times)

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Offline owlpower

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Stereoisomer question
« on: July 09, 2016, 07:52:19 AM »
https://upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Damascenone.png/200px-Damascenone.png

Beta-damasoenone (image in link above) can react with the following sets of reagents and conditions to give different products.Which set of reagents and conditions below will give the most number of stereo-isomers after the reaction?

A Br2 in CCl4
B LiAlH4 in dry ether
C 2,4-dinitrophenyihydrazine
D H2, nickel at high temperature

How do you solve questions involving stereoisomers as products? There are so many possible variants present. My guess is either A or D since Br/H can be added to beta-damascenone.

May I ask how do you solve question types like these? What are your thought processes?


Offline kriggy

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Re: Stereoisomer question
« Reply #1 on: July 09, 2016, 10:58:58 AM »
Try to figure out what can be the possible products with every one of those reagents.

Offline AWK

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Re: Stereoisomer question
« Reply #2 on: July 09, 2016, 02:33:15 PM »
Your structure has no chiral center. You always obtain a racemic mixture if reaction is stereospecific. Just look at mechanism of each reaction.
AWK

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