Problem: Propose a plausible synthesis for the following transformation by completing the reaction diagram: Reaction 1: a) H2; Pt b) HBr; ROOR c) H3O+ d) Conc. H2SO4 Intermediate A: Reaction 2: a) H2; Pt b) HC≡CNa c) Br2 d) HBr Intermediate B: Reaction 3: a) OsO4; NMO b) H2; Lindlar's Catalyst c) HC≡CNa d) NaNH2 Intermediate C: Reaction 4: a) H3O+ b) t-BuOK c) (1) O3; (2) H2O d) (1) O3; (2) DMS Predict the reagent(s) required to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne. a) HBr, ROOR b) 1) OsO4; 2) NaHSO3, H2O c) NaBr d) 1) xs NaNH2; 2) H3O+ e) HBr 

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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) H2; Pt 

b) HBr; ROOR 

c) H3O

d) Conc. H2SO

Intermediate A: 

Reaction 2: 

a) H2; Pt 

b) HC≡CNa 

c) Br2 

d) HBr 

Intermediate B: 

Reaction 3: 

a) OsO4; NMO 

b) H2; Lindlar's Catalyst 

c) HC≡CNa 

d) NaNH

Intermediate C: 

Reaction 4: 

a) H3O+ 

b) t-BuOK 

c) (1) O3; (2) H2

d) (1) O3; (2) DMS 

Predict the reagent(s) required to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne. 

a) HBr, ROOR 

b) 1) OsO4; 2) NaHSO3, H2

c) NaBr 

d) 1) xs NaNH2; 2) H3O+ 

e) HBr 

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