a) Interpretation: The structures of alkenes that would yield the alcohol shown on hydration are to be given. Among hydroboration-oxidation and oxymercuration-demercuration, which method could be used to prepare the alcohol also has to be stated. Concept introduction: The hydroboration reaction takes place with syn stereochemistry and results in a non-Markovnikov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with less number of alkyl substitutents. The oxymercuration-demercuration reaction takes place with anti stereochemistry and results in Markovnokov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with more number of alkyl substitutents. To give: The structures of alkenes that would yield the alcohol shown on hydration. To state: Among hydroboration-oxidation and oxymercuration-demercuration methods which method can be used to prepare the alcohol from alkenes.

Question

Select the reagent that you would use to convert an alkene to a Markovnikov (more substituted) alcohol without possibility of carbocation rearrangement. o H2SO4, H2O OBH3-THF, then H2O2, H2O, NaOH Hg(OAc)2, H2O, then NaBH4 o OsO4, TBHP, H2O

Answer 1

Question

Chapter 8.SE, Problem 23VC

Interpretation Introduction

a)

Interpretation:

The structures of alkenes that would yield the alcohol shown on hydration are to be given. Among hydroboration-oxidation and oxymercuration-demercuration, which method could be used to prepare the alcohol also has to be stated.

Concept introduction:

The hydroboration reaction takes place with syn stereochemistry and results in a non-Markovnikov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with less number of alkyl substitutents.

The oxymercuration-demercuration reaction takes place with anti stereochemistry and results in Markovnokov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with more number of alkyl substitutents.

To give:

The structures of alkenes that would yield the alcohol shown on hydration.

To state:

Among hydroboration-oxidation and oxymercuration-demercuration methods which method can be used to prepare the alcohol from alkenes.

Interpretation Introduction

b)

Interpretation:

The structures of alkenes that would yield the alcohol shown on hydration are to be given. Among hydroboration-oxidation and oxymercuration-demercuration, the method which can be used to prepare the alcohol also has to be stated.

Concept introduction:

The hydroboration reaction takes place with syn stereochemistry and results in a non-Markovnikov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with less number of alkyl substitutents.

The oxymercuration-demercuration reaction takes place with anti stereochemistry and results in Markovnokov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with more number of alkyl substitutents.

To give:

The structures of alkenes that would yield the alcohol shown on hydration.

To state:

Among hydroboration-oxidation and oxymercuration-demercuration, the method which can be used to prepare the alcohol.

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