Complcated Chemistry Reaction - impossible?

AI Thread Summary
The discussion revolves around a complex chemistry reaction involving multiple steps, including a 221 reaction that produces either anti-Markovnikov or Markovnikov bromides depending on the reagents used. The second step involves creating an organolithium or Grignard reagent, which is crucial for the subsequent reactions. Participants express confusion about the formation of a Grignard reagent when lithium is used and question discrepancies in carbon counts in the products. Clarifications are sought regarding the mechanics of the Grignard reaction and the transformation of double bonds. The conversation highlights the intricacies of organic chemistry reactions and the importance of understanding each step's implications.
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Complcated Chemistry Reaction - impossible??

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Help :(
My notes say:

Step 1 is a 221 reaction. If peroxides are used in your version, then the anti-Markovnikov bromide is formed. If your version had only HBr, the the Markovnikov bromide is formeed.

Step 2 creates organolithium or Grignard reagent (depending on your version).

Steps 3 is a strong acid (D2O) - strong base (organometallic carbon) reaction which gives a deuterated alkane.

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I managed to get A right but I can't get B right :(
 
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Why would you think you would get a grignard when you treat with lithium? Why does your answer show four carbons when your starting material is propene?
 


What exactly is the grignard reaction then?
Don't you just remove a C=C bond and make it a single C-C bond and add a another –Br bond to the end of one C atom ??
 
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