Question

Select the structural formula(s) for the product(s) obtained when 1-butene reacts with Hg(OAc)2 in THF and H2O, then NaBH4, OH-.

Answer 1

CH3CH2CH(OH)CH3

Step-by-step explanation:

This reaction follows the Markonikovs rule which states that the addition of an acid yo an assymetric alkene, the proton given off by the acid goes to the Carbon attached/with more hydrogen substituents and the rest of the acid ion goes to the Carbon with more alkyl substituents.

The reaction under goes 2 steps,

The first step called Oxymercuration involves the dissociation of Hg(OAc)2 into HgOAc+ and OAc-. The double bond in 1-butene (high electron site) bonds to an electron deficient HgOAc+ thereby forming an unstable complex, the lone pairs of oxygen in the water molecule (H2O) is attracted and a conplex is further formed with a proton on the now bonded H2O molecule.

To stabilise this, the proton(H+) is removed and then Deoxymercuration occurs. Deoxymercuration is simply removing the HgOAc+ molecule from the compound. This is done by the further reaction with the mixture of NaBH4 in alkaline medium; this is a string reducing reagent (reducting reagent - addition of excess Hydrogen) to form a secondary alcohol(Butan-2-ol)

Below us the mechanism in the attachment, i hope this was helpful.