Problem: In each reaction box, place the best reagent and conditions from the list below Br2      excess NaNH2      PBr3      2 equiv. NaNH2      NaBH4      CH3CH2Br      H2, Lindlar catalyst      CH3Br       Na, NH3 (l)      HBr      BH3/THF      H20, H2SO4, HgSO4      H2O2, NaOH, H20       

FREE Expert Solution

Given reaction: Addition of a methyl group at the end → possible via alkynides


Possible sequence of reactions:

1. Halogenation → form vicinal dihalides (Br2)

2. Double elimination + deprotonation → form alkyne then alkynide (excess NaNH2)

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Problem Details

In each reaction box, place the best reagent and conditions from the list below

 Br2      excess NaNH2      PBr3      2 equiv. NaNH2      NaBH     CH3CH2Br      H2, Lindlar catalyst      CH3Br       Na, NH3 (l)      HBr      BH3/THF      H20, H2SO4, HgSO4      H2O2, NaOH, H20       

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Addition Retrosynthesis concept. If you need more Addition Retrosynthesis practice, you can also practice Addition Retrosynthesis practice problems.