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Solutions_Manual_for_Organic_Chemistry_6th_Ed 429

Solutions_Manual_for_Organic_Chemistry_6th_Ed 429 - 1...

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18-54 (a) (] BuLi (] CH31 (] .. .. S X S S, .. .. .. . S S X S _C I H H H CH3 H C / eH , t / CH , C "c H2O: .. + ' H .. .. ' H : S : S ·· ' H ·· ' H HS S-H 0: II .. .. . C .... H 'CH3 (c) Mercuric ion, Hg 2 + , assists the hydrolysis in two ways. First, mercuric ion is a Lewis acid of moderate strength, performing the same function as a proton from a protic acid. The effectiveness of Hg 2 + as a Lewis acid is partly due to its charge: even complexed with a sulfur, the mercury atom still has a positive charge, attracting
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