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Question

The reagent that can effect the following conversion is:


A
(i) Br2/CCl4, (ii) NaNH2 (excess)/NH3 then CH3I, (iii) Na/NH3
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B
(i) Br2/CCl4, (ii) LiNH2 (excess)/NH3 then CH3I, (iii) Na/NH3, (iv) OsO4 then hydrolysis
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C
(i) Br2/CCl4, (ii) LiNH2 (excess)/NH3 then CH3I(excess),(iii) H2/Lindlar's catalyst, (iv) OsO4 then NaHSO3
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D
(i) NaNH2 (4 eq)/NH3 then CH3I(excess), (ii) OsO4 then NaHSO4
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Solution

The correct option is C (i) Br2/CCl4, (ii) LiNH2 (excess)/NH3 then CH3I(excess),(iii) H2/Lindlar's catalyst, (iv) OsO4 then NaHSO3

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