Problem: Propose a plausible synthesis for the following transformation by completing the reaction diagram: Reaction 1: a) (1) O3; (2) H2O b) HC≡CNa c) Br2, hv d) Br2, H2O Intermediate product A:Reaction 2: a) (1) Hg(OAc)2, H2O; (2) NaBH4 b) (1) BH3•THF; (2) H2O2, NaOH c) (1) NaOMe; (2) HBr, ROOR d) (1) t-BuOK; (2) HBr Intermediate product B: Reaction 3: a) OsO4, NMO b) EtI c) NaNH2 d) HC≡CNa Intermediate product C: Reaction 4: a) Conc. H2SO4 b) H2, Pt c) H2, Lindlar's Catalyst d) t-BuOK 

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We are asked to propose a plausible synthesis for the following transformation by completing the reaction diagram: 


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Problem Details

Propose a plausible synthesis for the following transformation by completing the reaction diagram: 

Reaction 1: 

a) (1) O3; (2) H2

b) HC≡CNa 

c) Br2, hv 

d) Br2, H2

Intermediate product A:

Reaction 2: 

a) (1) Hg(OAc)2, H2O; (2) NaBH4 

b) (1) BH3•THF; (2) H2O2, NaOH 

c) (1) NaOMe; (2) HBr, ROOR 

d) (1) t-BuOK; (2) HBr 

Intermediate product B: 

Reaction 3: 

a) OsO4, NMO 

b) EtI 

c) NaNH2 

d) HC≡CNa 

Intermediate product C: 

Reaction 4: 

a) Conc. H2SO4 

b) H2, Pt 

c) H2, Lindlar's Catalyst 

d) t-BuOK 



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