Organic Chemistry 331- CH 6

For the following reaction: 1) Add curved arrows for the first step. 2) Draw both the organic and inorganic intermediate species. Include nonbonding electrons and charges, where applicable. Include hydrogen atoms.

unknown

Alkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C-Hg bond to a C-H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structure of the Hg-containing compound and the final alcohol product formed in the following reaction sequence.

(Partially incorrect)