Match the correct reagents/conditions needed to form the products indicated (the

Question

Match the correct reagents/conditions needed to form the products indicated (there are 3 separate products) when treated with (E)-3-methylpent-2-ene.

(2S 3R)-2 3-dichloro-3-methylpentane

aqueous HCl

(2S 3R)-2-chloro-3-methylpentan-3-ol

Cl2

(2R 3S)-3-methylpentan-2-ol

Cl2 and water

Hg(OAc)2 in H2O followed by sodium borohydride

BH3 then hydrogen peroxide and NaOH

Match the correct reagents/conditions needed to form the products indicated (there are 3 separate products) when treated with (E)-3-methylpent-2-ene.

Explanation / Answer

1) (E)-3-methylpent-2-ene. + Cl2 ----> (2S 3R)-2 3-dichloro-3-methylpentane

2) (E)-3-methylpent-2-ene + aqueous HCl -----> (2S 3R)-2-chloro-3-methylpentan-3-ol

3) )-3-methylpent-2-ene + BH3/THF + H2O2 ----> (2R 3S)-3-methylpentan-2-ol

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