Chapter 12, Problem 12.23P

Interpretation Introduction

(a)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the $-\text{OH}$ group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(b)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. The hydrogen atom finishes up bound to the highly substituted carbon, and boron finishes up attached to the fewer substituted carbon atom in the double bond.

Interpretation Introduction

(c)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the $-\text{OH}$ group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.